6762:
1606:
53:
384:
243:
69:
43:
78:
1220:
1124:
1119:
1129:
1114:
7991:
1216:
6744:
7955:
1802:, electrophiles attack at the alpha position. The selectivity for alpha over beta substitution can be rationalized in terms of the resonance structures of the intermediate: for the alpha substitution intermediate, seven resonance structures can be drawn, of which four preserve an aromatic ring. For beta substitution, the intermediate has only six resonance structures, and only two of these are aromatic.
6753:
2423:(wetting agents) that effectively disperse colloidal systems in aqueous media. The major commercial applications are in the agricultural chemical industry, which uses ANS for wettable powder and wettable granular (dry-flowable) formulations, and in the textile and fabric industry, which uses the wetting and defoaming properties of ANS for bleaching and dyeing operations.
1219:
2459:
7979:
2078:
7967:
1221:
1395:
1645:
1635:
1567:
The molecule is planar, like benzene. Unlike benzene, the carbonâcarbon bonds in naphthalene are not of the same length. The bonds C1âC2, C3âC4, C5âC6 and C7âC8 are about 1.37 Ă
(137 pm) in length, whereas the other carbonâcarbon bonds are about 1.42 Ă
(142 pm) long. This difference, established by
1558:
nomenclature of derived compounds, those eight atoms are numbered 1 through 8 in sequence around the perimeter of the molecule, starting with a carbon atom adjacent to a shared one. The shared carbon atoms are labeled 4a (between 4 and 5) and 8a (between 8 and 1).
1137:
1094:
2100:
Naphthalene is the most abundant single component of coal tar. The composition of coal tar varies with coal type and processing, but typical coal tar is about 10% naphthalene by weight. In industrial practice,
1237:
4497:
1616:
across the plane of the shared carbon pair, as well as across the plane that bisects bonds C2-C3 and C6-C7, and across the plane of the carbon atoms. Thus there are two sets of equivalent hydrogen atoms: the
2668:, naphthalene is listed as "known to the State to cause cancer". A probable mechanism for the carcinogenic effects of mothballs and some types of air fresheners containing naphthalene has been identified.
2385:, precursors for various dyestuffs, pigments, rubber processing chemicals and other chemicals and pharmaceuticals. They are also used as dispersants in synthetic and natural rubbers, in agricultural
4065:
6526:
3644:
John Kidd (1821). "Observations on
Naphthalene, a peculiar substance resembling a concrete essential oil, which is produced during the decomposition of coal tar, by exposure to a red heat".
3601:
Amoore JE, Hautala E (1983). "Odor as an aid to chemical safety: Odor thresholds compared with threshold limit values and volatiles for 214 industrial chemicals in air and water dilution".
2160:
Inc., Ruetgers Canada Inc. and
Recochem Inc., and the primary petroleum producer is Monument Chemical Inc. In Western Europe the well-known producers are Koppers, Ruetgers, and Deza. In
3815:
Dieter Cremer; Thomas
Schmidt; Charles W. Bock (1985). "Theoretical determination of molecular structure and conformation. 14. Is bicyclodecapentaene aromatic or antiaromatic?".
3587:
3565:
2692:
2664:; and that hemolytic anemia (described above) can occur in children and infants after oral or inhalation exposure or after maternal exposure during pregnancy. Under California's
1335:
2306:
Molten naphthalene provides an excellent solubilizing medium for poorly soluble aromatic compounds. In many cases it is more efficient than other high-boiling solvents, such as
1408:
2129:
to isolate naphthalene. The crude naphthalene resulting from this process is about 95% naphthalene by weight. The chief impurities are the sulfur-containing aromatic compound
2610:(NTP) held an experiment where male and female rats and mice were exposed to naphthalene vapors on weekdays for two years. Both male and female rats exhibited evidence of
3949:
3772:
Cruickshank, D. W. J.; Sparks, R. A. (18 October 1960). "Experimental and
Theoretical Determinations of Bond Lengths in Naphthalene, Anthracene and Other Hydrocarbons".
1900:
The resulting lithionaphthalene undergoes a second lithiation, in contrast to the behavior of phenyllithium. These 1,8-dilithio derivatives are precursors to a host of
7775:
7695:
7511:
7446:
7386:
7314:
7220:
7114:
6984:
6535:
4488:
3238:
3154:
3740:
1222:
6519:
1692:. The resistivity drops more than a thousandfold on melting, to about 4 à 10 Ω m. Both in the liquid and in the solid, the resistivity depends on temperature as
1230:
2684:
4282:
2560:
2145:(< 2%). Petroleum-derived naphthalene is usually purer than that derived from coal tar. Where required, crude naphthalene can be further purified by
433:
4601:
2641:
4461:
4069:
6512:
4116:
M.A. Filatov; A.V. Cheprakov (2011). "The synthesis of new tetrabenzo- and tetranaphthoporphyrins via the addition reactions of 4,7-dihydroisoindole".
2338:
1511:(a broad term encompassing any volatile, flammable liquid hydrocarbon mixture, including coal tar). Naphthalene's chemical formula was determined by
4083:
K. Komatsua; Y. Murataa; N. Sugitaa; et al. (1993). "Use of naphthalene as a solvent for selective formation of the 1:1 DielsâAlder adduct of C
42:
3975:
van
Soolingen J, de Lang RJ, den Besten R, et al. (1995). "A simple procedure for the preparation of 1,8-bis(diphenylphosphino)naphthalene".
2676:
1244:
4631:
2274:. In a sealed container containing naphthalene pellets, naphthalene vapors build up to levels toxic to both the adult and larval forms of many
1605:
1025:
1183:
52:
4322:
3503:
3327:
3310:
3222:
976:
3257:
2243:
Naphthalene is used mainly as a precursor to derivative chemicals. The single largest use of naphthalene is the industrial production of
1503:
cited these two disclosures and then described many of this substance's properties and the means of its production. He proposed the name
4201:
2522:
1634:
8031:
7898:
4196:
3958:
68:
4519:
8026:
7798:
2645:
398:
3685:
2533:
Several uses stem from naphthalene's high volatility: it is used to create artificial pores in the manufacture of high-porosity
7923:
6107:
5556:
1548:
1460:
1071:
8041:
6098:
2538:
2405:
1057:
77:
1759:, naphthalene reacts more readily than benzene. For example, chlorination and bromination of naphthalene proceeds without a
3733:
7848:
3456:
3427:
2208:
2146:
7883:
1873:
1415:
1177:
341:
1776:
1128:
1123:
7079:
6416:
3122:
2680:
2607:
2374:
2149:
from any of a variety of solvents, resulting in 99% naphthalene by weight, referred to as 80 °C (melting point).
1811:
1807:
1554:
The eight carbon atoms that are not shared by the two rings carry one hydrogen atom each. For purpose of the standard
362:
3843:
1118:
102:
white tar, camphor tar, tar camphor, naphthalin, naphthaline, antimite, albocarbon, hexalene, mothballs, moth flakes
4624:
3206:
2696:
2688:
2563:, from which over 400 million people suffer. Humans, in particular children, have developed the condition known as
1660:
1359:
1346:
7838:
7833:
7646:
7014:
2700:
1629:
are then possible for mono-substituted naphthalenes, corresponding to substitution at an alpha or beta position.
856:
250:
2334:
7878:
7304:
7074:
7034:
6249:
4450:
4290:
1814:
as the thermodynamic product. The 1-isomer forms predominantly at 25 °C, and the 2-isomer at 160 °C.
1267:
4367:
7235:
7210:
7200:
3407:
1113:
7958:
5016:
3173:
2503:
2126:
2097:, but present-day production is mainly from coal tar. Approximately 1.3 million tons are produced annually.
2062:
1815:
1803:
780:
238:
7813:
7606:
6934:
6875:
6783:
6778:
6688:
6565:
6560:
5966:
5364:
4946:
4885:
4780:
952:
6939:
6610:
2717:, the use of naphthalene in mothballs is forbidden. Danger to human health and the common use of natural
2390:
8036:
8016:
7868:
7843:
7481:
7240:
7099:
7084:
7054:
6646:
6310:
6305:
6027:
5961:
5354:
4617:
4118:
2550:
1772:
1756:
1597:
1291:
1151:
1106:
728:
200:
90:
7170:
7150:
6823:
5349:
4870:
3712:
7195:
5336:
4857:
1491:
In the early 1820s, two separate reports described a white solid with a pungent odor derived from the
8021:
7929:
7913:
7538:
6909:
6880:
6761:
6585:
6295:
6290:
6285:
6280:
6203:
5545:
5344:
4928:
4158:
3902:
3855:
3781:
2416:
2323:
792:
605:
6833:
4197:"New propulsion system using the key ingredient in moth balls could propel satellites through space"
3349:
2622:
of the nose. Female mice exhibited some evidence of carcinogenesis based on increased incidences of
2571:, lack of appetite, restlessness, and pale skin. Exposure to large amounts of naphthalene may cause
1169:
7873:
7853:
7666:
7356:
7190:
6844:
6708:
6683:
6651:
6570:
6233:
5873:
5376:
4897:
4089:
3315:
3026:
2993:
2960:
2394:
2298:, and in museum storage-drawers and cupboards to protect the contents from attack by insect pests.
2271:
2089:. From the 1960s until the 1990s, significant amounts of naphthalene were also produced from heavy
1784:
1764:
1573:
1500:
1087:
575:
379:
114:
6860:
5422:
3391:
7971:
7893:
7863:
7808:
7685:
7661:
7406:
7160:
7094:
6959:
6919:
6803:
6770:
6733:
6693:
6672:
6615:
6590:
6351:
6091:
6060:
6017:
5437:
5432:
5417:
5002:
4875:
4865:
4339:
3797:
3661:
3626:
3232:
3059:
2623:
2358:
2350:
2244:
2231:
2014:
2006:
1913:
1768:
1613:
1468:
880:
160:
148:
6954:
5506:
5475:
5254:
5244:
5129:
6865:
5511:
5490:
5485:
5269:
5264:
5259:
5249:
5144:
5139:
5134:
5124:
4790:
7918:
7501:
7401:
7371:
7289:
7029:
6914:
6870:
6818:
6625:
6620:
6552:
6412:
6188:
5951:
5923:
5766:
5526:
5521:
5359:
4880:
4318:
4247:
4047:
4021:
3954:
3918:
3871:
3618:
3533:
3499:
3493:
3323:
3218:
2568:
2447:
2189:
2142:
2106:
1652:
1589:
1577:
1569:
1540:
1191:
1003:
850:
7049:
3203:
Nomenclature of
Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book)
7995:
7983:
7903:
7803:
7733:
7708:
7656:
7089:
6964:
6929:
6850:
6838:
6798:
6703:
6636:
6402:
6198:
6193:
5915:
4237:
4176:
4166:
4127:
4098:
4037:
3984:
3910:
3863:
3824:
3789:
3694:
3653:
3610:
3210:
2795:
2760:
2753:
2564:
2443:
2431:
2212:
2122:
2110:
1901:
1431:
900:
811:
612:
550:
456:
4595:
4573:
4312:
350:
7591:
7566:
7265:
7104:
7044:
7024:
6944:
6828:
6728:
6713:
6698:
6605:
6595:
6065:
6022:
5931:
5805:
4770:
4760:
4400:
4371:
4351:
3417:, National Institute of Standards and Technology, Gaithersburg (MD) (retrieved 2014-05-24)
2307:
1792:
1520:
1512:
1280:
583:
269:
4586:
2567:, after ingesting mothballs or deodorant blocks containing naphthalene. Symptoms include
220:
4287:
NTP Technical
Reports 410 and 500, available from NTP: Long-Term Abstracts & Reports
4162:
3906:
3859:
3785:
3385:
2703:
at 15 ppm (75 mg/m). Naphthalene's minimum odor threshold is 0.084 ppm for humans.
2541:; and it has been explored as a sublimable propellant for cold gas satellite thrusters.
383:
242:
180:
124:
7828:
7793:
7576:
7466:
7431:
7416:
7351:
7346:
7245:
7145:
7064:
7039:
7004:
6949:
6924:
6793:
6641:
6452:
6447:
6361:
6330:
6264:
6259:
6152:
5996:
5991:
5956:
5907:
5813:
4785:
4775:
4242:
4225:
2707:
2665:
2556:
2534:
2225:
2161:
2130:
1799:
1386:
758:
741:
598:
4102:
3890:
1912:
With alkali metals, naphthalene forms the dark blue-green radical anion salts such as
8010:
7858:
7713:
7596:
7571:
7552:
7496:
7376:
7334:
7329:
7069:
7059:
7019:
6894:
6788:
6743:
6718:
6600:
6580:
6084:
5673:
5480:
5470:
4966:
3947:
Gerd Collin; Hartmut Höke; Helmut Greim (2003). "Naphthalene and
Hydronaphthalenes".
3529:
2619:
2153:
1869:
1788:
1738:
is 0.73 in the solid. However, the solid shows semiconducting character below 100 K.
1524:
933:
537:
523:
231:
6504:
3801:
3665:
3630:
2105:
of coal tar yields an oil containing about 50% naphthalene, along with twelve other
1547:
if they share two or more atoms.) As such, naphthalene is classified as a benzenoid
1467:
with a characteristic odor that is detectable at concentrations as low as 0.08
1195:
7934:
7788:
7641:
7581:
7561:
7533:
7461:
7341:
7324:
7279:
7230:
7135:
6855:
6808:
6656:
6397:
6346:
6228:
6213:
6172:
6147:
6076:
5779:
5743:
5639:
5412:
5402:
5311:
5301:
5291:
4832:
4822:
4812:
3774:
Proceedings of the Royal
Society A: Mathematical, Physical and Engineering Sciences
2611:
2514:
2478:
2466:
2439:
2337:
adduct. The aromatization of hydroporphyrins has been achieved using a solution of
2315:
2311:
2102:
2094:
2066:
1752:
1593:
1492:
714:
4567:
4270:
2377:
and sulfonates are useful. Naphthalenesulfonic acids are used in the synthesis of
4042:
2172:, dedicated naphthalene and phenol makers INKOR, Yenakievsky Metallurgy plant in
1187:
7908:
7818:
7783:
7676:
7651:
7491:
7396:
7366:
7250:
7165:
7155:
6885:
6813:
6371:
6356:
6254:
5827:
5784:
5757:
5691:
5654:
5427:
5407:
5394:
5326:
5321:
5316:
5306:
5296:
5283:
5114:
4847:
4842:
4837:
4827:
4817:
4804:
4640:
4265:
4002:
3214:
2706:
Mothballs and other products containing naphthalene have been banned within the
2699:
at 10 ppm (50 mg/m) over an eight-hour time-weighted average, as well as a
2510:
2462:
2362:
2354:
1933:
1682:
1581:
1472:
1317:
1256:
1075:
864:
654:
314:
21:
3914:
3464:
3435:
1681:
Pure crystalline naphthalene is a moderate insulator at room temperature, with
7823:
7765:
7728:
7703:
7601:
7411:
7274:
6300:
6269:
6157:
5886:
5774:
5578:
5465:
5455:
5384:
5119:
4941:
4936:
4911:
4765:
4755:
4579:
4425:
4131:
3988:
3561:
3168:
3164:
2864:
2729:
The partial list of naphthalene derivatives includes the following compounds:
2644:(IARC) classifies naphthalene as possibly carcinogenic to humans and animals (
2627:
2518:
2499:
2420:
2386:
2382:
2378:
2330:
2279:
2270:, although its use has largely been replaced in favor of alternatives such as
2220:
2177:
2165:
1079:
710:
690:
674:
670:
650:
630:
569:
478:
211:
3922:
3875:
3698:
7755:
7620:
7456:
7260:
7140:
6994:
6969:
6493:
6483:
6478:
6407:
6315:
6223:
6167:
5891:
5629:
5598:
5588:
5583:
5460:
5188:
4976:
4971:
4750:
4171:
4146:
3579:
3319:
3159:
2572:
2398:
2283:
2090:
2058:
1760:
1083:
830:
4383:
4251:
4051:
3793:
3657:
3614:
1165:
4561:
3622:
3209:. 2014. pp. 13, 35, 204, 207, 221â222, 302, 457, 461, 469, 601, 650.
7723:
7635:
7436:
7299:
7284:
7255:
7124:
6899:
6723:
6667:
6661:
6630:
6575:
6543:
6488:
6442:
6432:
6422:
6392:
6376:
6366:
6320:
6208:
6162:
6121:
6055:
6050:
5860:
5852:
5844:
5724:
5716:
5708:
5659:
5644:
5634:
5624:
5619:
5593:
5516:
5228:
5208:
5058:
4986:
4981:
4961:
3891:"Observation of the Band-Hopping Transition for Electrons in Naphthalene"
3145:
2649:
2596:
2584:
2580:
2493:
2485:
2435:
2267:
2263:
2248:
2216:
2200:
2193:
2086:
2010:
1962:
1937:
1496:
1480:
1447:
1243:
1236:
1229:
1202:
25:
3828:
2458:
2077:
7888:
7718:
7671:
7630:
7586:
7528:
7523:
7486:
7476:
7471:
7426:
7421:
7361:
7294:
7185:
7180:
7130:
7009:
6999:
6752:
6457:
6437:
6427:
6126:
6012:
5986:
5836:
5681:
5614:
5213:
5203:
5193:
5083:
5073:
5063:
4951:
4917:
4905:
4719:
4709:
4699:
4689:
4181:
3149:
3136:
2718:
2691:
at 10 ppm (50 mg/m) over an eight-hour time-weighted average. The
2630:
2615:
2489:
2474:
2427:
2295:
2229:
produce naphthalene among a range of volatile organic compounds, while
2173:
2157:
1966:
1656:
1536:
1516:
1508:
1476:
1464:
634:
623:
619:
587:
579:
509:
301:
251:
17:
3867:
1779:
conditions, naphthalene can also be easily alkylated by reaction with
1771:, respectively. Likewise, whereas both benzene and naphthalene can be
7939:
7760:
7742:
7205:
7175:
6677:
6325:
6218:
5881:
5800:
5700:
5649:
5223:
5218:
5198:
5158:
5098:
5093:
5088:
5078:
5068:
5029:
4956:
4734:
4729:
4724:
4714:
4704:
4694:
4659:
3141:
2657:
2576:
2319:
2291:
2169:
2138:
2134:
2118:
1780:
1727:
1626:
1436:
694:
191:
4145:
Tsifakis, Dimitrios; Charles, Christine; Boswell, Rod (2020-09-23).
3680:
1385:
Except where otherwise noted, data are given for materials in their
1161:
4364:
2333:
is conveniently conducted in refluxing naphthalene to give the 1:1
1872:
is the conversion of 1-bromonaphthalene to 1-lithionaphthalene, by
289:
6974:
6904:
6473:
5565:
5531:
5447:
4594:
4489:"Holy straight bananas â now the Eurocrats are banning moth balls"
2714:
2661:
2600:
2592:
2588:
2457:
2287:
2076:
1689:
1644:
1643:
1585:
1555:
325:
171:
147:
137:
4314:
IARC Monographs on the
Evaluation of Carcinogenic Risks to Humans
2211:, possibly produced by the termite as a repellant against "ants,
1475:
hydrocarbon, naphthalene's structure consists of a fused pair of
2850:
2634:
2559:, most commonly in people with the inherited condition known as
2537:; it is used in engineering studies of heat transfer using mass
2397:
are used as precursors and to form pharmaceutical salts such as
2275:
2204:
2114:
1535:
A naphthalene molecule can be viewed as the fusion of a pair of
1372:
499:
280:
6508:
6080:
4613:
4609:
4020:
Daisy BH, Strobel GA, Castillo U, et al. (November 2002).
3498:. New York: Springer Science+Business Media, Inc. p. 288.
2555:
Exposure to large amounts of naphthalene may damage or destroy
2419:(ANS) are used in many industrial applications as nondetergent
1157:
4384:"Scientists May Have Solved Mystery Of Carcinogenic Mothballs"
2653:
2438:. They are produced by treating naphthalenesulfonic acid with
2409:
1686:
3584:
Immediately Dangerous to Life or Health Concentrations (IDLH)
3410:
in Linstrom, Peter J.; Mallard, William G. (eds.);
1860:
Further sulfonation give di-, tri-, and tetrasulfonic acids.
4426:"CDC - NIOSH Pocket Guide to Chemical Hazards - Naphthalene"
3748:
Naphthalene is a PAH that is produced commercially in the US
3390:(2nd ed.). New York: D. Van Nostrand Company. pp.
1576:
model in naphthalene and in particular, with the theorem of
367:
51:
41:
3263:. United States Environmental Protection Agency. 2014-04-23
2637:, while male mice exhibited no evidence of carcinogenesis.
2349:
The single largest use of naphthalene is the production of
2057:
This reaction is the basis of the main use of naphthalene.
921:α = 90°, ÎČ = 122.92°, Îł = 90°
3412:
2509:
Substituted naphthalenes serve as pharmaceuticals such as
2484:
Hydrogenation of naphthalene gives tetrahydronaphthalene (
1655:
of naphthalene that have two fused aromatic rings include
2599:(yellow coloration of the skin due to dysfunction of the
1214:
4226:"Association of naphthalene with acute hemolytic anemia"
4605:. Vol. 19 (11th ed.). 1911. pp. 167â168.
4147:"Naphthalene as a Cubesat Cold Gas Thruster Propellant"
2648:). The IARC also points out that acute exposure causes
2061:
can also be effected using conventional stoichiometric
1965:. Further hydrogenation yields decahydronaphthalene or
1403:
2282:
uses of naphthalene include use in soil as a fumigant
3588:
National Institute for Occupational Safety and Health
3566:
National Institute for Occupational Safety and Health
2693:
National Institute for Occupational Safety and Health
2164:, naphthalene is produced by a variety of integrated
1929:. The naphthalene anions are strong reducing agents.
4520:"Council warned against use of poisonous moth balls"
2506:, which are useful as nonvolatile liquids for inks.
46:
Skeletal formula and numbering system of naphthalene
7774:
7694:
7619:
7510:
7445:
7385:
7313:
7219:
7113:
6983:
6769:
6551:
6542:
6466:
6385:
6339:
6242:
6181:
6140:
6114:
6043:
6005:
5979:
5944:
5900:
5872:
5835:
5826:
5793:
5765:
5756:
5736:
5699:
5690:
5672:
5607:
5564:
5555:
5544:
5499:
5446:
5393:
5375:
5335:
5282:
5237:
5181:
5157:
5107:
5051:
5028:
5015:
4995:
4927:
4896:
4856:
4803:
4743:
4682:
4658:
4647:
2561:
glucose-6-phosphate dehydrogenase (G6PD) deficiency
1818:to give the 1- and 2-sulfonic acid occurs readily:
4582:âCDC â NIOSH Pocket Guide to Chemical Hazards
4487:
4374:, Office of Environmental Health Hazard Assessment
4022:"Naphthalene, an insect repellent, is produced by
3889:Schein, L. B.; Duke, C. B.; McGhie, A. R. (1978).
2502:of naphthalene with propylene gives a mixture of
3258:"Ambient Water Quality Criteria for Naphthalene"
3155:List of interstellar and circumstellar molecules
2496:. Tetralin is used as a hydrogen-donor solvent.
2247:, although more phthalic anhydride is made from
1580:. This theorem would describe naphthalene as an
1479:rings. It is the main ingredient of traditional
313:
4546:ćœćĄéąç»èŽžćăć«çéšć
łäșćæąçäș§ćéćźèäžžæćĄäœżçšæšèć¶ćçéç„ïŒćœç»èŽžè°ïŒ1993ïŒ64ć·ïŒ
4405:Environmental Health Association of Nova Scotia
2408:are precursors for synthesis of many synthetic
1218:
542:217.97 °C (424.35 °F; 491.12 K)
407:InChI=1S/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H
123:
3950:Ullmann's Encyclopedia of Industrial Chemistry
417:InChI=1/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H
6520:
6092:
4625:
3495:Structure and Chemistry of Crystalline Solids
3387:Solubility of Inorganic and Organic Compounds
3384:Seidell, Atherton; Linke, William F. (1919).
2685:Occupational Safety and Health Administration
2199:Trace amounts of naphthalene are produced by
2168:complexes (Severstal, Evraz, Mechel, MMK) in
1936:under high pressure in the presence of metal
1596:), which is consistent with two of its three
530:80.26 °C (176.47 °F; 353.41 K)
8:
3681:"Studien ĂŒber die s. g. aromatischen SĂ€uren"
3415:, NIST Standard Reference Database Number 69
3237:: CS1 maint: DOI inactive as of June 2024 (
2393:plates. Naphthalenedisulfonic acids such as
2109:. This oil, after being washed with aqueous
1621:positions, numbered 1, 4, 5, and 8, and the
1612:Because of this resonance, the molecule has
4590:in the Pesticide Properties DataBase (PPDB)
3343:
3341:
3339:
3252:
3250:
3248:
2642:International Agency for Research on Cancer
1734:is absolute temperature (K). The parameter
1666:The point group symmetry of naphthalene is
528:78.2 °C (172.8 °F; 351.3 K)
6548:
6527:
6513:
6505:
6099:
6085:
6077:
5832:
5762:
5696:
5687:
5561:
5552:
5178:
5048:
5025:
4679:
4655:
4632:
4618:
4610:
3942:
3940:
3938:
3936:
3934:
3932:
382:
241:
219:
30:
4241:
4180:
4170:
4041:
3734:"Polycyclic Aromatic Hydrocarbons (PAHs)"
3492:Douglas, Bodie E.; Ho, Shih-Ming (2007).
2434:used for the production of high strength
2235:produces naphthalene almost exclusively.
1726:is the Boltzmann constant (8.617 Ă 10 eV/
1659:, which has a 5â7 fused ring system, and
1366:TWA 10 ppm (50 mg/m) ST 15 ppm (75 mg/m)
349:
4003:"Termite 'mothball' keep insects at bay"
3713:"Ueber die Constitution des Naphthalins"
3560:NIOSH Pocket Guide to Chemical Hazards.
3525:
3523:
3521:
3519:
3517:
3515:
2731:
2353:, which is an intermediate used to make
2266:. It was once the primary ingredient in
1852:
1848:
1844:
1840:
1836:
1832:
1828:
1824:
1507:, as it had been derived from a kind of
3555:
3553:
3551:
3487:
3485:
3483:
3481:
3185:
2365:polymers used in paints and varnishes.
438:
403:
378:
4564:âNational Pesticide Information Center
4401:"Mothballs, air fresheners and cancer"
4347:
4337:
3403:
3401:
3379:
3377:
3375:
3373:
3371:
3369:
3303:
3301:
3299:
3297:
3230:
3092:1,2,7-Trimethylnaphthalene (Sapotalin)
2477:are produced from naphthalene. Useful
1940:to give 1,2,3,4-tetrahydronaphthalene(
1275:525 °C (977 °F; 798 K)
232:
3428:"Thermal Conductivity of Naphthalene"
3311:CRC Handbook of Chemistry and Physics
3295:
3293:
3291:
3289:
3287:
3285:
3283:
3281:
3279:
3277:
1261:80 °C (176 °F; 353 K)
504:Strong odor of coal tar or mothballs
410:Key: UFWIBTONFRDIAS-UHFFFAOYSA-N
199:
179:
7:
2492:), which are used as low-volatility
2121:), and with sulfuric acid to remove
1515:in 1826. The structure of two fused
4283:"NTP Technical Reports 410 and 500"
4202:Australian Broadcasting Corporation
4066:"Summary of Possum Repellent Study"
3715:(On the structure of naphthalene),
2523:nonsteroidal anti-inflammatory drug
1663:which has a fused 4â8 ring system.
420:Key: UFWIBTONFRDIAS-UHFFFAOYAC
304:
288:
56:Ball-and-stick model of naphthalene
7899:Nexus for Exoplanet System Science
4576:âmostly on toxicity of naphthalene
4518:Gray, Kerrina (17 November 2013).
4243:10.1111/j.1553-2712.2000.tb01889.x
3457:"Dynamic Viscosity of Naphthalene"
2721:are cited as reasons for the ban.
2442:, followed by neutralization with
14:
7799:Atomic and molecular astrophysics
6536:Molecules detected in outer space
3844:"Semiconductivity of Naphthalene"
3746:from the original on 2014-11-30.
2085:Most naphthalene is derived from
1298:10 ppm (TWA), 15 ppm (STEL)
7989:
7977:
7965:
7954:
7953:
6760:
6751:
6742:
6108:Polycyclic aromatic hydrocarbons
4486:Alderson, Andrew (15 Nov 2008).
3717:Annalen der Chemie und Pharmacie
3686:Annalen der Chemie und Pharmacie
1633:
1604:
1393:
1127:
1122:
1117:
1112:
468:
76:
67:
7924:Polycyclic aromatic hydrocarbon
4500:from the original on 2022-01-12
4467:from the original on 2016-10-14
4224:Santucci K, Shah B (Jan 2000).
3848:The Journal of Chemical Physics
3176:(classic naphthalene synthesis)
2481:include naphthoxyacetic acids.
2262:Naphthalene has been used as a
1625:positions, 2, 3, 6, and 7. Two
1549:polycyclic aromatic hydrocarbon
1461:polycyclic aromatic hydrocarbon
1389:(at 25 °C , 100 kPa).
2406:aminonaphthalenesulfonic acids
2192:are the major constituents of
2176:and ArcelorMittal Temirtau in
1868:Analogous to the synthesis of
1722:(eV) are constant parameters,
1058:Occupational safety and health
462:
1:
7849:Extraterrestrial liquid water
4103:10.1016/S0040-4039(00)61362-X
2683:to naphthalene exposure. The
2614:with increased incidences of
2369:Sulfonic acids and sulfonates
2209:Formosan subterranean termite
2184:Other sources and occurrences
2156:, the coal tar producers are
1340:(US health exposure limits):
1328:1200 mg/kg (guinea pig, oral)
494:White solid crystals/ flakes
4043:10.1099/00221287-148-11-3737
4026:, a novel endophytic fungus"
3348:Anatolievich, Kiper Ruslan.
3308:Lide, David R., ed. (2009).
2681:occupational exposure limits
2488:) and decahydronaphthalene (
2278:that attack textiles. Other
2219:worms". Some strains of the
2117:components (chiefly various
1747:Reactions with electrophiles
1326:490 mg/kg (rat, intravenous)
7080:Protonated hydrogen cyanide
3545:Naphthalene carcinogenicity
3215:10.1039/9781849733069-FP001
3123:Naphthalene-2-sulfonic acid
2608:National Toxicology Program
1812:naphthalene-2-sulfonic acid
1810:as the kinetic product but
1808:naphthalene-1-sulfonic acid
1306:or concentration (LD, LC):
914: = 6.003 Ă
,
910: = 8.235 Ă
,
37:
8058:
4009:. BBC News. April 8, 1998.
3915:10.1103/PhysRevLett.40.197
3842:Bornmann, John A. (1962).
3646:Philosophical Transactions
3207:Royal Society of Chemistry
2697:recommended exposure limit
2689:permissible exposure limit
2548:
2426:Some naphthalenesulfonate
2188:Naphthalene and its alkyl
1806:gives the "alpha" product
1523:in 1866, and confirmed by
15:
8032:IARC Group 2B carcinogens
7948:
7839:Earliest known life forms
7834:Diffuse interstellar band
7305:Protonated cyanoacetylene
7075:Protonated carbon dioxide
7035:Hydromagnesium isocyanide
6740:
4545:
4132:10.1016/j.tet.2011.01.052
3989:10.1080/00397919508015858
2701:short-term exposure limit
2375:naphthalenesulfonic acids
1584:benzene unit bonded to a
1572:, is consistent with the
1383:
1334:
1302:
1093:
1055:
1050:
926:
918: = 8.658 Ă
843:
449:
429:
394:
107:
99:
89:
84:
75:
66:
36:
8027:Hazardous air pollutants
7884:Ironâsulfur world theory
7879:Photodissociation region
7582:Methyl-cyano-diacetylene
6274:-Benzopyrene(Olympicene)
4570:âEPA Air Toxics Web Site
4526:. Newsquest (London) Ltd
4266:MedlinePlus Encyclopedia
3977:Synthetic Communications
3699:10.1002/jlac.18661370309
3679:Emil Erlenmeyer (1866).
3192:Naphthalene: trade names
1874:lithiumâhalogen exchange
1330:533 mg/kg (mouse, oral)
1178:Precautionary statements
805:0.1052 W/m·K (479.72 K)
16:Not to be confused with
7959:Category:Astrochemistry
7549:, fullerene, buckyball)
7236:Cyanobutadiynyl radical
7211:Silicon-carbide cluster
7201:Protonated formaldehyde
4602:EncyclopĂŠdia Britannica
4172:10.3389/fphy.2020.00389
3953:. Weinheim: Wiley-VCH.
3895:Physical Review Letters
3217:(inactive 2024-06-22).
3174:Wagner-Jauregg reaction
2725:Naphthalene derivatives
2504:diisopropylnaphthalenes
2127:fractional distillation
1908:Reduction and oxidation
1777:FriedelâCrafts reaction
1677:Electrical conductivity
1592:to it (at least in the
803:0.1152 W/m·K (418.37 K)
801:0.1174 W/m·K (400.22 K)
799:0.1219 W/m·K (372.22 K)
781:Magnetic susceptibility
7972:Outer space portal
7814:Circumstellar envelope
6779:Aluminium(I) hydroxide
6689:Phosphorus mononitride
6566:Aluminium monofluoride
6561:Aluminium monochloride
5967:1,3,5-Triheptylbenzene
4072:on September 28, 2013.
3794:10.1098/rspa.1960.0187
3658:10.1098/rstl.1821.0017
3615:10.1002/jat.2550030603
3413:NIST Chemistry WebBook
2470:
2417:naphthalene sulfonates
2125:components, undergoes
2082:
1757:substitution reactions
1649:
1519:rings was proposed by
1324:1800 mg/kg (rat, oral)
1225:
723:131.6 g/100 g (60 °C)
721:22.1 g/100 g (21.5 °C)
719:13.6 g/100 g (6.75 °C)
663:31.1 g/100 g (42.5 °C)
661:13.1 g/100 g (21.5 °C)
57:
47:
8042:Simple aromatic rings
7869:Interplanetary medium
7844:Extraterrestrial life
7482:Octatetraynyl radical
7100:Tricarbon monosulfide
6647:Magnesium monohydride
6250:Benzacephenanthrylene
5962:1,3,5-Triethylbenzene
4574:Naphthalene (PIM 363)
4271:Naphthalene poisoning
2551:Naphthalene poisoning
2461:
2454:Other derivative uses
2080:
1647:
1459:. It is the simplest
1353:TWA 10 ppm (50 mg/m)
1292:Threshold limit value
1224:
705:78.8 g/100 g (70 °C)
685:87.2 g/100 g (70 °C)
659:6.8 g/100 g (6.75 °C)
564:238.1 mg/L (73.4 °C)
518:0.9625 g/cm (100 °C)
55:
45:
7996:Chemistry portal
7984:Astronomy portal
7930:RNA world hypothesis
7914:PAH world hypothesis
7607:Heptatrienyl radical
7539:Buckminsterfullerene
7427:Methylcyanoacetylene
6935:Silicon carbonitride
6910:Methylidynephosphane
6876:Magnesium isocyanide
6784:Aluminium isocyanide
6586:Carbon monophosphide
5365:Isopropylcyclohexene
4947:Perhydrophenanthrene
4886:Isopropylcyclohexane
4151:Frontiers in Physics
2829:1-Naphthoyl chloride
2294:and animals such as
2203:and some species of
2141:(< 2%), and
1588:but not extensively
1207:(fire diamond)
793:Thermal conductivity
703:30.8 g/100 g (40 °C)
701:17.5 g/100 g (25 °C)
683:49.5 g/100 g (40 °C)
681:35.5 g/100 g (25 °C)
665:111 g/100 g (60 °C)
645:179 g/100 g (70 °C)
643:19.5 g/100 g (40 °C)
641:11.3 g/100 g (25 °C)
514:1.145 g/cm (15.5 °C)
7874:Interstellar medium
7854:Forbidden mechanism
7667:Hydrogen isocyanide
7357:Hexatriynyl radical
6940:c-Silicon dicarbide
6845:Hydrogen isocyanide
6709:Silicon monosulfide
6684:Phosphorus monoxide
6652:Methylidyne radical
6611:Fluoromethylidynium
6571:Aluminium(II) oxide
6234:Tricyclobutabenzene
6061:Alicyclic compounds
5874:Tetramethylbenzenes
4596:"Naphthalene"
4524:Your Local Guardian
4293:on October 24, 2004
4163:2020FrP.....8..389T
4090:Tetrahedron Letters
3907:1978PhRvL..40..197S
3860:1962JChPh..36.1691B
3829:10.1021/jo00215a018
3786:1960RSPSA.258..270C
3316:Boca Raton, Florida
3027:2-Chloronaphthalene
2994:1-Chloronaphthalene
2961:1-Fluoronaphthalene
2272:1,4-dichlorobenzene
2005:in the presence of
1932:Naphthalene can be
1765:1-chloronaphthalene
1742:Chemical properties
1661:Bicyclodecapentaene
1531:Physical properties
1527:three years later.
679:19.5 g/100 g (0 °C)
560:43.9 mg/L (34.5 °C)
551:Solubility in water
516:1.0253 g/cm (20 °C)
486: g·mol
161:Beilstein Reference
33:
7894:Molecules in stars
7864:Intergalactic dust
7809:Circumstellar dust
7751:Naphthalene cation
7686:Trihydrogen cation
7662:Hydrogen deuteride
7587:Methyltriacetylene
7422:Hexapentaenylidene
7241:E-Cyanomethanimine
7161:Cyclopropenylidene
7095:Tricarbon monoxide
7085:Silicon tricarbide
7055:Methylene amidogen
7045:Isothiocyanic acid
6960:Thioxoethenylidene
6920:Trihydrogen cation
6734:Titanium(II) oxide
6694:Potassium chloride
6673:Sulfur mononitride
6616:Helium hydride ion
6591:Carbon monosulfide
6018:Cyclopropenylidene
5355:Methylcyclopentene
5345:Methylcyclopropene
4876:Methylcyclopentane
4866:Methylcyclopropane
4370:2019-07-29 at the
4087:with anthracene".
4036:(Pt 11): 3737â41.
4024:Muscodor vitigenus
3762:, P-14.4 NUMBERING
3060:1-Bromonaphthalene
2926:1-Nitronaphthalene
2679:agencies have set
2471:
2389:, in dyes, and in
2359:polyvinyl chloride
2351:phthalic anhydride
2322:. The reaction of
2245:phthalic anhydride
2232:Muscodor vitigenus
2107:aromatic compounds
2095:petroleum refining
2083:
2015:phthalic anhydride
2007:vanadium pentoxide
1914:sodium naphthalene
1769:1-bromonaphthalene
1653:Structural isomers
1650:
1614:bilateral symmetry
1563:Molecular geometry
1416:Infobox references
1375:(Immediate danger)
1226:
839:0.217 cP (150 °C)
774:0.42438 L·atm/mol
699:5.5 g/100 g (0 °C)
58:
48:
31:
8004:
8003:
7919:Pseudo-panspermia
7615:
7614:
7562:Cyanodecapentayne
7502:N-Methylformamide
7477:Methyldiacetylene
7402:Aminoacetonitrile
7372:Methyl isocyanate
7290:Methyl isocyanide
7171:Isocyanoacetylene
7151:Cyanoformaldehyde
7030:Hydrogen peroxide
6915:Potassium cyanide
6871:Magnesium cyanide
6824:Disilicon carbide
6819:Dicarbon monoxide
6626:Hydrogen fluoride
6621:Hydrogen chloride
6502:
6501:
6413:Hexabenzocoronene
6296:Benzofluoranthene
6291:Benzofluoranthene
6286:Benzofluoranthene
6281:Benzofluoranthene
6204:Benzophenanthrene
6074:
6073:
6039:
6038:
5975:
5974:
5952:Hexamethylbenzene
5940:
5939:
5822:
5821:
5767:Trimethylbenzenes
5752:
5751:
5668:
5667:
5540:
5539:
5527:Cyclododecatriene
5522:Cyclooctatetraene
5360:Methylcyclohexene
5350:Methylcyclobutene
5337:Alkylcycloalkenes
5278:
5277:
5153:
5152:
5011:
5010:
4881:Methylcyclohexane
4871:Methylcyclobutane
4858:Alkylcycloalkanes
4799:
4798:
4324:978-92-832-1282-9
4205:. 8 December 2021
4126:(19): 3559â3566.
4097:(52): 8473â8476.
3983:(11): 1741â1744.
3868:10.1063/1.1732805
3823:(15): 2684â2688.
3780:(1293): 270â285.
3711:C. Graebe (1869)
3530:Sigma-Aldrich Co.
3505:978-0-387-26147-8
3329:978-1-4200-9084-0
3314:(90th ed.).
3224:978-0-85404-182-4
3205:. Cambridge: The
3128:
3127:
2448:calcium hydroxide
2432:superplasticizers
2391:leadâacid battery
2207:, as well as the
2147:recrystallization
2143:methylnaphthalene
2093:fractions during
1961:), also known as
1578:cross-conjugation
1570:X-ray diffraction
1541:organic chemistry
1465:crystalline solid
1463:, and is a white
1424:Chemical compound
1422:
1421:
1152:Hazard statements
1004:Gibbs free energy
851:Crystal structure
837:0.761 cP (100 °C)
752:2.5 kPa (100 °C)
562:80.9 mg/L (50 °C)
558:31.6 mg/L (25 °C)
363:CompTox Dashboard
149:Interactive image
62:
61:
8049:
7994:
7993:
7992:
7982:
7981:
7980:
7970:
7969:
7968:
7957:
7956:
7904:Organic compound
7804:Chemical formula
7709:Dihydroxyacetone
7657:Hydrogen cyanide
7342:Cyanodiacetylene
7196:Propadienylidene
7090:Thioformaldehyde
6965:Titanium dioxide
6930:Sodium hydroxide
6851:Hydrogen sulfide
6839:Hydrogen cyanide
6799:Carbonyl sulfide
6764:
6755:
6746:
6704:Silicon monoxide
6637:Hydroxyl radical
6549:
6529:
6522:
6515:
6506:
6403:Diindenoperylene
6311:Dibenzanthracene
6306:Dibenzanthracene
6301:trans-Bicalicene
6101:
6094:
6087:
6078:
6031:-Propenylbenzene
5833:
5763:
5697:
5688:
5562:
5553:
5238:Branched alkynes
5179:
5108:Branched alkenes
5049:
5026:
4929:Polycycloalkanes
4914:(bicycloheptane)
4908:(bicyclopentane)
4744:Branched alkanes
4680:
4656:
4634:
4627:
4620:
4611:
4606:
4598:
4550:
4549:
4547:
4541:
4535:
4534:
4532:
4531:
4515:
4509:
4508:
4506:
4505:
4491:
4483:
4477:
4476:
4474:
4472:
4466:
4455:
4447:
4441:
4440:
4438:
4436:
4422:
4416:
4415:
4413:
4411:
4397:
4391:
4390:, June 20, 2006.
4381:
4375:
4362:
4356:
4355:
4349:
4345:
4343:
4335:
4333:
4331:
4309:
4303:
4302:
4300:
4298:
4289:. Archived from
4279:
4273:
4262:
4256:
4255:
4245:
4221:
4215:
4214:
4212:
4210:
4193:
4187:
4186:
4184:
4174:
4142:
4136:
4135:
4113:
4107:
4106:
4080:
4074:
4073:
4068:. Archived from
4062:
4056:
4055:
4045:
4017:
4011:
4010:
3999:
3993:
3992:
3972:
3966:
3964:
3944:
3927:
3926:
3886:
3880:
3879:
3854:(6): 1691â1692.
3839:
3833:
3832:
3812:
3806:
3805:
3769:
3763:
3757:
3751:
3750:
3745:
3738:
3730:
3724:
3709:
3703:
3702:
3676:
3670:
3669:
3641:
3635:
3634:
3598:
3592:
3591:
3576:
3570:
3569:
3557:
3546:
3543:
3537:
3527:
3510:
3509:
3489:
3476:
3475:
3473:
3472:
3463:. Archived from
3453:
3447:
3446:
3444:
3443:
3434:. Archived from
3424:
3418:
3405:
3396:
3395:
3381:
3364:
3363:
3361:
3360:
3345:
3334:
3333:
3305:
3272:
3271:
3269:
3268:
3262:
3254:
3243:
3242:
3236:
3228:
3199:
3193:
3190:
2897:1-Naphthaldehyde
2796:2-Naphthoic acid
2761:1-Naphthoic acid
2754:Refractive index
2738:Chemical formula
2732:
2565:hemolytic anemia
2444:sodium hydroxide
2395:Armstrong's acid
2341:in naphthalene.
2290:spaces to repel
2133:(< 2%),
2111:sodium hydroxide
2004:
2003:
2002:
1989:
1988:
1987:
1979:
1978:
1960:
1959:
1958:
1950:
1949:
1928:
1927:
1902:peri-naphthalene
1888:Br + BuLi â C
1856:
1637:
1608:
1458:
1457:
1456:
1446:
1445:
1432:organic compound
1406:
1400:
1397:
1396:
1281:Explosive limits
1246:
1239:
1232:
1217:
1197:
1193:
1189:
1185:
1171:
1167:
1163:
1159:
1131:
1126:
1121:
1116:
1082:. Dust can form
1042:
1015:
993:
966:
942:
927:Thermochemistry
901:Lattice constant
894:
893:
835:0.964 cP (80 °C)
812:Refractive index
787:-91.9·10 cm/mol
750:0.93 kPa (80 °C)
639:5 g/100 g (0 °C)
584:Carboxylic acids
485:
470:
464:
457:Chemical formula
387:
386:
371:
369:
353:
317:
306:
292:
270:Gmelin Reference
253:
245:
234:
223:
203:
183:
151:
127:
80:
71:
38:
34:
8057:
8056:
8052:
8051:
8050:
8048:
8047:
8046:
8007:
8006:
8005:
8000:
7990:
7988:
7978:
7976:
7966:
7964:
7944:
7770:
7746:
7737:
7690:
7680:
7623:
7611:
7592:Propionaldehyde
7567:Ethylene glycol
7556:
7548:
7544:
7515:
7513:
7506:
7462:Cyanohexatriyne
7448:
7441:
7388:
7381:
7316:
7309:
7269:
7222:
7215:
7186:Methoxy radical
7116:
7109:
7105:Thiocyanic acid
6986:
6979:
6889:
6829:Ethynyl radical
6765:
6759:
6758:
6757:
6756:
6750:
6749:
6748:
6747:
6738:
6729:Sulfur monoxide
6714:Sodium chloride
6699:Silicon carbide
6606:Diatomic carbon
6596:Carbon monoxide
6538:
6533:
6503:
6498:
6467:General classes
6462:
6381:
6335:
6238:
6177:
6136:
6110:
6105:
6075:
6070:
6066:Petroleum jelly
6035:
6023:Phenylacetylene
6001:
5971:
5936:
5932:Isobutylbenzene
5896:
5868:
5818:
5789:
5748:
5732:
5686:
5664:
5603:
5547:
5536:
5495:
5442:
5389:
5371:
5331:
5274:
5233:
5175:
5167:
5161:
5149:
5103:
5045:
5038:
5032:
5021:
5019:
5007:
4991:
4923:
4920:(bicyclodecane)
4892:
4852:
4795:
4761:3-Methylpentane
4739:
4676:
4668:
4662:
4651:
4649:
4643:
4638:
4593:
4558:
4553:
4543:
4542:
4538:
4529:
4527:
4517:
4516:
4512:
4503:
4501:
4485:
4484:
4480:
4470:
4468:
4464:
4453:
4449:
4448:
4444:
4434:
4432:
4424:
4423:
4419:
4409:
4407:
4399:
4398:
4394:
4382:
4378:
4372:Wayback Machine
4363:
4359:
4346:
4336:
4329:
4327:
4325:
4311:
4310:
4306:
4296:
4294:
4281:
4280:
4276:
4263:
4259:
4223:
4222:
4218:
4208:
4206:
4195:
4194:
4190:
4144:
4143:
4139:
4115:
4114:
4110:
4086:
4082:
4081:
4077:
4064:
4063:
4059:
4019:
4018:
4014:
4001:
4000:
3996:
3974:
3973:
3969:
3961:
3946:
3945:
3930:
3888:
3887:
3883:
3841:
3840:
3836:
3814:
3813:
3809:
3771:
3770:
3766:
3758:
3754:
3743:
3736:
3732:
3731:
3727:
3710:
3706:
3678:
3677:
3673:
3643:
3642:
3638:
3600:
3599:
3595:
3578:
3577:
3573:
3559:
3558:
3549:
3544:
3540:
3528:
3513:
3506:
3491:
3490:
3479:
3470:
3468:
3455:
3454:
3450:
3441:
3439:
3426:
3425:
3421:
3406:
3399:
3383:
3382:
3367:
3358:
3356:
3347:
3346:
3337:
3330:
3307:
3306:
3275:
3266:
3264:
3260:
3256:
3255:
3246:
3229:
3225:
3201:
3200:
3196:
3191:
3187:
3183:
3133:
3102:
3098:
3071:
3067:
3038:
3034:
3005:
3001:
2972:
2968:
2940:
2936:
2932:
2907:
2903:
2876:
2872:
2839:
2835:
2811:
2807:
2803:
2776:
2772:
2768:
2727:
2674:
2557:red blood cells
2553:
2547:
2535:grinding wheels
2531:
2456:
2371:
2347:
2345:Derivative uses
2327:
2308:dichlorobenzene
2304:
2260:
2241:
2213:poisonous fungi
2186:
2075:
2052:
2048:
2044:
2040:
2036:
2032:
2028:
2024:
2001:
1998:
1997:
1996:
1994:
1993:Oxidation with
1986:
1983:
1982:
1981:
1977:
1974:
1973:
1972:
1970:
1957:
1954:
1953:
1952:
1948:
1945:
1944:
1943:
1941:
1926:
1923:
1922:
1921:
1919:
1910:
1895:
1891:
1887:
1883:
1866:
1854:
1850:
1846:
1842:
1838:
1834:
1830:
1826:
1822:
1793:phosphoric acid
1749:
1744:
1717:
1702:
1679:
1671:
1641:
1565:
1533:
1521:Emil Erlenmeyer
1513:Michael Faraday
1489:
1455:
1452:
1451:
1450:
1444:
1441:
1440:
1439:
1435:
1425:
1418:
1413:
1412:
1411: ?)
1402:
1398:
1394:
1390:
1376:
1363:
1350:
1329:
1327:
1325:
1321:
1315:
1295:
1272:
1269:
1251:
1250:
1249:
1248:
1241:
1234:
1227:
1223:
1215:
1180:
1154:
1140:
1109:
1068:
1046:-5156.3 kJ/mol
1043:
1040:
1034:
1030:
1027:
1026:Std enthalpy of
1019:201.585 kJ/mol
1016:
1010:
1006:
994:
991:
985:
981:
978:
977:Std enthalpy of
970:167.39 J/mol·K
967:
964:
957:
954:
946:165.72 J/mol·K
943:
936:
922:
919:
903:
892:
889:
888:
887:
883:
873:
867:
853:
838:
836:
822:
820:
804:
802:
800:
798:
784:
771:
769:
760:
751:
749:
748:23.6 Pa (30 °C)
747:
746:8.64 Pa (20 °C)
722:
720:
704:
702:
700:
684:
682:
680:
664:
662:
660:
644:
642:
640:
616:
609:
602:
595:
591:
563:
561:
559:
557:
556:19 mg/L (10 °C)
553:
543:
531:
529:
517:
515:
483:
473:
467:
459:
445:
442:
437:
436:
425:
422:
421:
418:
412:
411:
408:
402:
401:
390:
372:
365:
356:
336:
320:
307:
295:
272:
263:
226:
206:
186:
163:
154:
141:
130:
117:
103:
95:
29:
12:
11:
5:
8055:
8053:
8045:
8044:
8039:
8034:
8029:
8024:
8019:
8009:
8008:
8002:
8001:
7999:
7998:
7986:
7974:
7962:
7949:
7946:
7945:
7943:
7942:
7937:
7932:
7927:
7921:
7916:
7911:
7906:
7901:
7896:
7891:
7886:
7881:
7876:
7871:
7866:
7861:
7856:
7851:
7846:
7841:
7836:
7831:
7829:Cosmochemistry
7826:
7821:
7816:
7811:
7806:
7801:
7796:
7794:Astrochemistry
7791:
7786:
7780:
7778:
7772:
7771:
7769:
7768:
7763:
7758:
7753:
7748:
7744:
7740:
7735:
7731:
7726:
7721:
7716:
7711:
7706:
7700:
7698:
7692:
7691:
7689:
7688:
7683:
7678:
7674:
7669:
7664:
7659:
7654:
7649:
7647:Formyl radical
7644:
7639:
7633:
7627:
7625:
7617:
7616:
7613:
7612:
7610:
7609:
7604:
7599:
7594:
7589:
7584:
7579:
7577:Methyl acetate
7574:
7569:
7564:
7559:
7554:
7550:
7546:
7542:
7536:
7531:
7526:
7520:
7518:
7508:
7507:
7505:
7504:
7499:
7494:
7489:
7484:
7479:
7474:
7469:
7467:Dimethyl ether
7464:
7459:
7453:
7451:
7443:
7442:
7440:
7439:
7434:
7432:Methyl formate
7429:
7424:
7419:
7417:Glycolaldehyde
7414:
7409:
7404:
7399:
7393:
7391:
7383:
7382:
7380:
7379:
7374:
7369:
7364:
7359:
7354:
7352:Glycolonitrile
7349:
7347:Ethylene oxide
7344:
7339:
7338:
7337:
7327:
7321:
7319:
7311:
7310:
7308:
7307:
7302:
7297:
7292:
7287:
7282:
7277:
7272:
7267:
7263:
7258:
7253:
7248:
7246:Cyclopropenone
7243:
7238:
7233:
7227:
7225:
7217:
7216:
7214:
7213:
7208:
7203:
7198:
7193:
7188:
7183:
7178:
7173:
7168:
7163:
7158:
7153:
7148:
7146:Cyanoacetylene
7143:
7138:
7133:
7128:
7121:
7119:
7111:
7110:
7108:
7107:
7102:
7097:
7092:
7087:
7082:
7077:
7072:
7067:
7065:Methyl radical
7062:
7057:
7052:
7047:
7042:
7040:Isocyanic acid
7037:
7032:
7027:
7022:
7017:
7012:
7007:
7005:Isocyanic acid
7002:
6997:
6991:
6989:
6981:
6980:
6978:
6977:
6972:
6967:
6962:
6957:
6952:
6950:Sulfur dioxide
6947:
6942:
6937:
6932:
6927:
6925:Sodium cyanide
6922:
6917:
6912:
6907:
6902:
6897:
6892:
6887:
6883:
6878:
6873:
6868:
6863:
6858:
6853:
6848:
6842:
6836:
6834:Formyl radical
6831:
6826:
6821:
6816:
6811:
6806:
6801:
6796:
6794:Carbon dioxide
6791:
6786:
6781:
6775:
6773:
6767:
6766:
6741:
6739:
6737:
6736:
6731:
6726:
6721:
6716:
6711:
6706:
6701:
6696:
6691:
6686:
6681:
6675:
6670:
6665:
6659:
6654:
6649:
6644:
6642:Iron(II) oxide
6639:
6634:
6628:
6623:
6618:
6613:
6608:
6603:
6598:
6593:
6588:
6583:
6578:
6573:
6568:
6563:
6557:
6555:
6546:
6540:
6539:
6534:
6532:
6531:
6524:
6517:
6509:
6500:
6499:
6497:
6496:
6491:
6486:
6481:
6476:
6470:
6468:
6464:
6463:
6461:
6460:
6455:
6453:Trinaphthylene
6450:
6448:Superphenalene
6445:
6440:
6435:
6430:
6425:
6420:
6410:
6405:
6400:
6395:
6389:
6387:
6383:
6382:
6380:
6379:
6374:
6369:
6364:
6362:Dibenzopyrenes
6359:
6354:
6349:
6343:
6341:
6337:
6336:
6334:
6333:
6331:Tetraphenylene
6328:
6323:
6318:
6313:
6308:
6303:
6298:
6293:
6288:
6283:
6278:
6277:
6276:
6267:
6262:
6252:
6246:
6244:
6240:
6239:
6237:
6236:
6231:
6226:
6221:
6216:
6211:
6206:
6201:
6196:
6191:
6189:Benzanthracene
6185:
6183:
6179:
6178:
6176:
6175:
6170:
6165:
6160:
6155:
6153:Acenaphthylene
6150:
6144:
6142:
6138:
6137:
6135:
6134:
6129:
6124:
6118:
6116:
6112:
6111:
6106:
6104:
6103:
6096:
6089:
6081:
6072:
6071:
6069:
6068:
6063:
6058:
6053:
6047:
6045:
6041:
6040:
6037:
6036:
6034:
6033:
6025:
6020:
6015:
6009:
6007:
6003:
6002:
6000:
5999:
5997:4-Vinyltoluene
5994:
5992:Divinylbenzene
5989:
5983:
5981:
5977:
5976:
5973:
5972:
5970:
5969:
5964:
5959:
5957:2-Phenylhexane
5954:
5948:
5946:
5942:
5941:
5938:
5937:
5935:
5934:
5929:
5921:
5913:
5904:
5902:
5898:
5897:
5895:
5894:
5889:
5884:
5878:
5876:
5870:
5869:
5867:
5866:
5858:
5850:
5841:
5839:
5830:
5824:
5823:
5820:
5819:
5817:
5816:
5814:4-Ethyltoluene
5811:
5809:-Propylbenzene
5803:
5797:
5795:
5791:
5790:
5788:
5787:
5782:
5777:
5771:
5769:
5760:
5754:
5753:
5750:
5749:
5747:
5746:
5740:
5738:
5734:
5733:
5731:
5730:
5722:
5714:
5705:
5703:
5694:
5685:
5684:
5678:
5676:
5670:
5669:
5666:
5665:
5663:
5662:
5657:
5652:
5647:
5642:
5637:
5632:
5627:
5622:
5617:
5611:
5609:
5605:
5604:
5602:
5601:
5596:
5591:
5586:
5581:
5576:
5570:
5568:
5559:
5550:
5542:
5541:
5538:
5537:
5535:
5534:
5529:
5524:
5519:
5514:
5509:
5503:
5501:
5497:
5496:
5494:
5493:
5488:
5483:
5478:
5473:
5468:
5463:
5458:
5452:
5450:
5444:
5443:
5441:
5440:
5435:
5430:
5425:
5420:
5415:
5410:
5405:
5399:
5397:
5391:
5390:
5388:
5387:
5381:
5379:
5377:Bicycloalkenes
5373:
5372:
5370:
5369:
5367:
5362:
5357:
5352:
5347:
5341:
5339:
5333:
5332:
5330:
5329:
5324:
5319:
5314:
5309:
5304:
5299:
5294:
5288:
5286:
5280:
5279:
5276:
5275:
5273:
5272:
5267:
5262:
5257:
5252:
5247:
5241:
5239:
5235:
5234:
5232:
5231:
5226:
5221:
5216:
5211:
5206:
5201:
5196:
5191:
5185:
5183:
5182:Linear alkynes
5176:
5169:
5163:
5155:
5154:
5151:
5150:
5148:
5147:
5142:
5137:
5132:
5127:
5122:
5117:
5111:
5109:
5105:
5104:
5102:
5101:
5096:
5091:
5086:
5081:
5076:
5071:
5066:
5061:
5055:
5053:
5052:Linear alkenes
5046:
5040:
5034:
5023:
5013:
5012:
5009:
5008:
5006:
5005:
4999:
4997:
4993:
4992:
4990:
4989:
4984:
4979:
4974:
4969:
4964:
4959:
4954:
4949:
4944:
4939:
4933:
4931:
4925:
4924:
4922:
4921:
4915:
4909:
4902:
4900:
4898:Bicycloalkanes
4894:
4893:
4891:
4890:
4888:
4883:
4878:
4873:
4868:
4862:
4860:
4854:
4853:
4851:
4850:
4845:
4840:
4835:
4830:
4825:
4820:
4815:
4809:
4807:
4801:
4800:
4797:
4796:
4794:
4793:
4788:
4783:
4778:
4773:
4768:
4763:
4758:
4753:
4747:
4745:
4741:
4740:
4738:
4737:
4732:
4727:
4722:
4717:
4712:
4707:
4702:
4697:
4692:
4686:
4684:
4683:Linear alkanes
4677:
4670:
4664:
4653:
4645:
4644:
4639:
4637:
4636:
4629:
4622:
4614:
4608:
4607:
4591:
4583:
4577:
4571:
4565:
4557:
4556:External links
4554:
4552:
4551:
4536:
4510:
4478:
4442:
4417:
4392:
4376:
4365:Proposition 65
4357:
4323:
4304:
4274:
4257:
4230:Acad Emerg Med
4216:
4188:
4137:
4108:
4084:
4075:
4057:
4012:
3994:
3967:
3960:978-3527306732
3959:
3928:
3901:(3): 197â200.
3881:
3834:
3807:
3764:
3752:
3725:
3723: : 20â28.
3704:
3693:(3): 327â359.
3671:
3636:
3609:(6): 272â290.
3603:J Appl Toxicol
3593:
3571:
3547:
3538:
3511:
3504:
3477:
3448:
3419:
3397:
3365:
3335:
3328:
3273:
3244:
3223:
3194:
3184:
3182:
3179:
3178:
3177:
3171:
3162:
3157:
3152:
3139:
3132:
3129:
3126:
3125:
3119:
3118:
3115:
3112:
3109:
3106:
3103:
3100:
3096:
3093:
3089:
3088:
3085:
3082:
3079:
3076:
3073:
3069:
3065:
3062:
3056:
3055:
3052:
3049:
3046:
3043:
3040:
3036:
3032:
3029:
3023:
3022:
3019:
3016:
3013:
3010:
3007:
3003:
2999:
2996:
2990:
2989:
2986:
2983:
2980:
2977:
2974:
2970:
2966:
2963:
2957:
2956:
2953:
2950:
2947:
2944:
2941:
2938:
2934:
2930:
2927:
2923:
2922:
2920:
2918:
2915:
2912:
2909:
2905:
2901:
2898:
2894:
2893:
2890:
2887:
2884:
2881:
2878:
2874:
2870:
2867:
2861:
2860:
2857:
2854:
2847:
2844:
2841:
2837:
2833:
2830:
2826:
2825:
2822:
2820:
2818:
2815:
2812:
2809:
2805:
2801:
2798:
2792:
2791:
2788:
2786:
2783:
2780:
2777:
2774:
2770:
2766:
2763:
2757:
2756:
2751:
2748:
2747:Boiling point
2745:
2744:Melting point
2742:
2739:
2736:
2726:
2723:
2673:
2670:
2666:Proposition 65
2612:carcinogenesis
2549:Main article:
2546:
2545:Health effects
2543:
2530:
2527:
2455:
2452:
2370:
2367:
2361:, and to make
2346:
2343:
2325:
2303:
2300:
2259:
2256:
2240:
2237:
2226:Muscodor albus
2185:
2182:
2162:Eastern Europe
2131:benzothiophene
2074:
2071:
2055:
2054:
2050:
2046:
2042:
2038:
2034:
2030:
2026:
2022:
1999:
1984:
1975:
1955:
1946:
1924:
1917:
1909:
1906:
1898:
1897:
1893:
1889:
1885:
1881:
1865:
1862:
1858:
1857:
1800:regiochemistry
1748:
1745:
1743:
1740:
1715:
1700:
1678:
1675:
1669:
1639:
1638:
1610:
1609:
1564:
1561:
1532:
1529:
1488:
1485:
1453:
1442:
1423:
1420:
1419:
1414:
1392:
1391:
1387:standard state
1384:
1381:
1380:
1377:
1371:
1368:
1367:
1364:
1358:
1355:
1354:
1351:
1345:
1342:
1341:
1332:
1331:
1322:
1313:
1311:
1308:
1307:
1300:
1299:
1296:
1290:
1287:
1286:
1283:
1277:
1276:
1273:
1266:
1263:
1262:
1259:
1253:
1252:
1242:
1235:
1228:
1213:
1212:
1211:
1210:
1208:
1199:
1198:
1181:
1176:
1173:
1172:
1155:
1150:
1147:
1146:
1141:
1136:
1133:
1132:
1110:
1105:
1102:
1101:
1091:
1090:
1086:mixtures with
1069:
1066:
1063:
1062:
1053:
1052:
1048:
1047:
1044:
1038:
1032:
1024:
1021:
1020:
1017:
1008:
1002:
999:
998:
995:
989:
983:
975:
972:
971:
968:
962:
951:
948:
947:
944:
932:
929:
928:
924:
923:
920:
906:
904:
899:
896:
895:
890:
884:
879:
876:
875:
871:
868:
863:
860:
859:
854:
849:
846:
845:
841:
840:
833:
827:
826:
823:
818:
810:
807:
806:
795:
789:
788:
785:
779:
776:
775:
772:
767:
757:
754:
753:
744:
742:Vapor pressure
738:
737:
734:
725:
724:
717:
707:
706:
697:
687:
686:
677:
667:
666:
657:
647:
646:
637:
627:
626:
614:
607:
600:
593:
589:
572:
566:
565:
554:
549:
546:
545:
540:
534:
533:
526:
520:
519:
512:
506:
505:
502:
496:
495:
492:
488:
487:
481:
475:
474:
471:
465:
460:
455:
452:
451:
447:
446:
444:
443:
441:c1c2ccccc2ccc1
440:
432:
431:
430:
427:
426:
424:
423:
419:
416:
415:
413:
409:
406:
405:
397:
396:
395:
392:
391:
389:
388:
375:
373:
361:
358:
357:
355:
354:
346:
344:
338:
337:
335:
334:
330:
328:
322:
321:
319:
318:
310:
308:
300:
297:
296:
294:
293:
285:
283:
277:
276:
273:
268:
265:
264:
262:
261:
257:
255:
247:
246:
236:
228:
227:
225:
224:
216:
214:
208:
207:
205:
204:
196:
194:
188:
187:
185:
184:
176:
174:
168:
167:
164:
159:
156:
155:
153:
152:
144:
142:
135:
132:
131:
129:
128:
120:
118:
113:
110:
109:
105:
104:
101:
97:
96:
93:
87:
86:
82:
81:
73:
72:
64:
63:
60:
59:
49:
13:
10:
9:
6:
4:
3:
2:
8054:
8043:
8040:
8038:
8035:
8033:
8030:
8028:
8025:
8023:
8020:
8018:
8015:
8014:
8012:
7997:
7987:
7985:
7975:
7973:
7963:
7961:
7960:
7951:
7950:
7947:
7941:
7938:
7936:
7933:
7931:
7928:
7925:
7922:
7920:
7917:
7915:
7912:
7910:
7907:
7905:
7902:
7900:
7897:
7895:
7892:
7890:
7887:
7885:
7882:
7880:
7877:
7875:
7872:
7870:
7867:
7865:
7862:
7860:
7859:Homochirality
7857:
7855:
7852:
7850:
7847:
7845:
7842:
7840:
7837:
7835:
7832:
7830:
7827:
7825:
7822:
7820:
7817:
7815:
7812:
7810:
7807:
7805:
7802:
7800:
7797:
7795:
7792:
7790:
7787:
7785:
7782:
7781:
7779:
7777:
7773:
7767:
7764:
7762:
7759:
7757:
7754:
7752:
7749:
7747:
7741:
7739:
7732:
7730:
7727:
7725:
7722:
7720:
7717:
7715:
7714:Methoxyethane
7712:
7710:
7707:
7705:
7702:
7701:
7699:
7697:
7693:
7687:
7684:
7682:
7675:
7673:
7670:
7668:
7665:
7663:
7660:
7658:
7655:
7653:
7650:
7648:
7645:
7643:
7640:
7637:
7634:
7632:
7629:
7628:
7626:
7622:
7618:
7608:
7605:
7603:
7600:
7598:
7597:Butyronitrile
7595:
7593:
7590:
7588:
7585:
7583:
7580:
7578:
7575:
7573:
7572:Ethyl formate
7570:
7568:
7565:
7563:
7560:
7558:
7551:
7540:
7537:
7535:
7532:
7530:
7527:
7525:
7522:
7521:
7519:
7517:
7509:
7503:
7500:
7498:
7497:Propionitrile
7495:
7493:
7490:
7488:
7485:
7483:
7480:
7478:
7475:
7473:
7470:
7468:
7465:
7463:
7460:
7458:
7455:
7454:
7452:
7450:
7444:
7438:
7435:
7433:
7430:
7428:
7425:
7423:
7420:
7418:
7415:
7413:
7410:
7408:
7405:
7403:
7400:
7398:
7395:
7394:
7392:
7390:
7384:
7378:
7377:Vinyl alcohol
7375:
7373:
7370:
7368:
7365:
7363:
7360:
7358:
7355:
7353:
7350:
7348:
7345:
7343:
7340:
7336:
7335:Vinyl cyanide
7333:
7332:
7331:
7330:Acrylonitrile
7328:
7326:
7323:
7322:
7320:
7318:
7312:
7306:
7303:
7301:
7298:
7296:
7295:Pentynylidyne
7293:
7291:
7288:
7286:
7283:
7281:
7278:
7276:
7273:
7271:
7264:
7262:
7259:
7257:
7254:
7252:
7249:
7247:
7244:
7242:
7239:
7237:
7234:
7232:
7229:
7228:
7226:
7224:
7218:
7212:
7209:
7207:
7204:
7202:
7199:
7197:
7194:
7192:
7191:Methylenimine
7189:
7187:
7184:
7182:
7179:
7177:
7174:
7172:
7169:
7167:
7164:
7162:
7159:
7157:
7154:
7152:
7149:
7147:
7144:
7142:
7139:
7137:
7134:
7132:
7129:
7126:
7123:
7122:
7120:
7118:
7112:
7106:
7103:
7101:
7098:
7096:
7093:
7091:
7088:
7086:
7083:
7081:
7078:
7076:
7073:
7071:
7070:Propynylidyne
7068:
7066:
7063:
7061:
7060:Methyl cation
7058:
7056:
7053:
7051:
7048:
7046:
7043:
7041:
7038:
7036:
7033:
7031:
7028:
7026:
7023:
7021:
7020:Fulminic acid
7018:
7016:
7013:
7011:
7008:
7006:
7003:
7001:
6998:
6996:
6993:
6992:
6990:
6988:
6982:
6976:
6973:
6971:
6968:
6966:
6963:
6961:
6958:
6956:
6953:
6951:
6948:
6946:
6943:
6941:
6938:
6936:
6933:
6931:
6928:
6926:
6923:
6921:
6918:
6916:
6913:
6911:
6908:
6906:
6903:
6901:
6898:
6896:
6895:Nitrous oxide
6893:
6891:
6884:
6882:
6879:
6877:
6874:
6872:
6869:
6867:
6864:
6862:
6859:
6857:
6854:
6852:
6849:
6846:
6843:
6840:
6837:
6835:
6832:
6830:
6827:
6825:
6822:
6820:
6817:
6815:
6812:
6810:
6807:
6805:
6802:
6800:
6797:
6795:
6792:
6790:
6789:Amino radical
6787:
6785:
6782:
6780:
6777:
6776:
6774:
6772:
6768:
6763:
6754:
6745:
6735:
6732:
6730:
6727:
6725:
6722:
6720:
6719:Sodium iodide
6717:
6715:
6712:
6710:
6707:
6705:
6702:
6700:
6697:
6695:
6692:
6690:
6687:
6685:
6682:
6679:
6676:
6674:
6671:
6669:
6666:
6663:
6660:
6658:
6655:
6653:
6650:
6648:
6645:
6643:
6640:
6638:
6635:
6632:
6629:
6627:
6624:
6622:
6619:
6617:
6614:
6612:
6609:
6607:
6604:
6602:
6601:Cyano radical
6599:
6597:
6594:
6592:
6589:
6587:
6584:
6582:
6581:Carbon cation
6579:
6577:
6574:
6572:
6569:
6567:
6564:
6562:
6559:
6558:
6556:
6554:
6550:
6547:
6545:
6541:
6537:
6530:
6525:
6523:
6518:
6516:
6511:
6510:
6507:
6495:
6492:
6490:
6487:
6485:
6482:
6480:
6477:
6475:
6472:
6471:
6469:
6465:
6459:
6456:
6454:
6451:
6449:
6446:
6444:
6441:
6439:
6436:
6434:
6431:
6429:
6426:
6424:
6421:
6418:
6414:
6411:
6409:
6406:
6404:
6401:
6399:
6396:
6394:
6391:
6390:
6388:
6384:
6378:
6375:
6373:
6370:
6368:
6365:
6363:
6360:
6358:
6355:
6353:
6352:Benzoperylene
6350:
6348:
6345:
6344:
6342:
6338:
6332:
6329:
6327:
6324:
6322:
6319:
6317:
6314:
6312:
6309:
6307:
6304:
6302:
6299:
6297:
6294:
6292:
6289:
6287:
6284:
6282:
6279:
6275:
6273:
6268:
6266:
6263:
6261:
6258:
6257:
6256:
6253:
6251:
6248:
6247:
6245:
6241:
6235:
6232:
6230:
6227:
6225:
6222:
6220:
6217:
6215:
6212:
6210:
6207:
6205:
6202:
6200:
6199:Benzofluorene
6197:
6195:
6194:Benzofluorene
6192:
6190:
6187:
6186:
6184:
6180:
6174:
6171:
6169:
6166:
6164:
6161:
6159:
6156:
6154:
6151:
6149:
6146:
6145:
6143:
6139:
6133:
6130:
6128:
6125:
6123:
6120:
6119:
6117:
6113:
6109:
6102:
6097:
6095:
6090:
6088:
6083:
6082:
6079:
6067:
6064:
6062:
6059:
6057:
6054:
6052:
6049:
6048:
6046:
6042:
6032:
6030:
6026:
6024:
6021:
6019:
6016:
6014:
6011:
6010:
6008:
6004:
5998:
5995:
5993:
5990:
5988:
5985:
5984:
5982:
5980:Vinylbenzenes
5978:
5968:
5965:
5963:
5960:
5958:
5955:
5953:
5950:
5949:
5947:
5943:
5933:
5930:
5928:
5927:-Butylbenzene
5926:
5922:
5920:
5919:-Butylbenzene
5918:
5914:
5912:
5911:-Butylbenzene
5910:
5906:
5905:
5903:
5899:
5893:
5890:
5888:
5885:
5883:
5880:
5879:
5877:
5875:
5871:
5865:
5863:
5859:
5857:
5855:
5851:
5849:
5847:
5843:
5842:
5840:
5838:
5834:
5831:
5829:
5825:
5815:
5812:
5810:
5808:
5804:
5802:
5799:
5798:
5796:
5792:
5786:
5783:
5781:
5778:
5776:
5773:
5772:
5770:
5768:
5764:
5761:
5759:
5755:
5745:
5742:
5741:
5739:
5735:
5729:
5727:
5723:
5721:
5719:
5715:
5713:
5711:
5707:
5706:
5704:
5702:
5698:
5695:
5693:
5689:
5683:
5680:
5679:
5677:
5675:
5674:Alkylbenzenes
5671:
5661:
5658:
5656:
5653:
5651:
5648:
5646:
5643:
5641:
5638:
5636:
5633:
5631:
5628:
5626:
5623:
5621:
5618:
5616:
5613:
5612:
5610:
5606:
5600:
5597:
5595:
5592:
5590:
5587:
5585:
5582:
5580:
5577:
5575:
5572:
5571:
5569:
5567:
5563:
5560:
5558:
5554:
5551:
5549:
5543:
5533:
5530:
5528:
5525:
5523:
5520:
5518:
5515:
5513:
5510:
5508:
5505:
5504:
5502:
5498:
5492:
5489:
5487:
5484:
5482:
5479:
5477:
5474:
5472:
5469:
5467:
5464:
5462:
5459:
5457:
5454:
5453:
5451:
5449:
5445:
5439:
5436:
5434:
5431:
5429:
5426:
5424:
5421:
5419:
5416:
5414:
5411:
5409:
5406:
5404:
5401:
5400:
5398:
5396:
5392:
5386:
5383:
5382:
5380:
5378:
5374:
5368:
5366:
5363:
5361:
5358:
5356:
5353:
5351:
5348:
5346:
5343:
5342:
5340:
5338:
5334:
5328:
5325:
5323:
5320:
5318:
5315:
5313:
5310:
5308:
5305:
5303:
5300:
5298:
5295:
5293:
5290:
5289:
5287:
5285:
5281:
5271:
5268:
5266:
5263:
5261:
5258:
5256:
5253:
5251:
5248:
5246:
5243:
5242:
5240:
5236:
5230:
5227:
5225:
5222:
5220:
5217:
5215:
5212:
5210:
5207:
5205:
5202:
5200:
5197:
5195:
5192:
5190:
5187:
5186:
5184:
5180:
5177:
5173:
5166:
5160:
5156:
5146:
5143:
5141:
5138:
5136:
5133:
5131:
5128:
5126:
5123:
5121:
5118:
5116:
5113:
5112:
5110:
5106:
5100:
5097:
5095:
5092:
5090:
5087:
5085:
5082:
5080:
5077:
5075:
5072:
5070:
5067:
5065:
5062:
5060:
5057:
5056:
5054:
5050:
5047:
5044:
5037:
5031:
5027:
5024:
5018:
5014:
5004:
5001:
5000:
4998:
4994:
4988:
4985:
4983:
4980:
4978:
4975:
4973:
4970:
4968:
4967:Dodecahedrane
4965:
4963:
4960:
4958:
4955:
4953:
4950:
4948:
4945:
4943:
4940:
4938:
4935:
4934:
4932:
4930:
4926:
4919:
4916:
4913:
4910:
4907:
4904:
4903:
4901:
4899:
4895:
4889:
4887:
4884:
4882:
4879:
4877:
4874:
4872:
4869:
4867:
4864:
4863:
4861:
4859:
4855:
4849:
4846:
4844:
4841:
4839:
4836:
4834:
4831:
4829:
4826:
4824:
4821:
4819:
4816:
4814:
4811:
4810:
4808:
4806:
4802:
4792:
4789:
4787:
4784:
4782:
4779:
4777:
4774:
4772:
4769:
4767:
4764:
4762:
4759:
4757:
4754:
4752:
4749:
4748:
4746:
4742:
4736:
4733:
4731:
4728:
4726:
4723:
4721:
4718:
4716:
4713:
4711:
4708:
4706:
4703:
4701:
4698:
4696:
4693:
4691:
4688:
4687:
4685:
4681:
4678:
4674:
4667:
4661:
4657:
4654:
4646:
4642:
4635:
4630:
4628:
4623:
4621:
4616:
4615:
4612:
4604:
4603:
4597:
4592:
4589:
4588:
4584:
4581:
4578:
4575:
4572:
4569:
4566:
4563:
4560:
4559:
4555:
4548:
4540:
4537:
4525:
4521:
4514:
4511:
4499:
4495:
4494:The Telegraph
4490:
4482:
4479:
4463:
4459:
4452:
4451:"Naphthalene"
4446:
4443:
4431:
4427:
4421:
4418:
4406:
4402:
4396:
4393:
4389:
4385:
4380:
4377:
4373:
4369:
4366:
4361:
4358:
4353:
4341:
4326:
4320:
4316:
4315:
4308:
4305:
4292:
4288:
4284:
4278:
4275:
4272:
4268:
4267:
4261:
4258:
4253:
4249:
4244:
4239:
4235:
4231:
4227:
4220:
4217:
4204:
4203:
4198:
4192:
4189:
4183:
4178:
4173:
4168:
4164:
4160:
4156:
4152:
4148:
4141:
4138:
4133:
4129:
4125:
4121:
4120:
4112:
4109:
4104:
4100:
4096:
4092:
4091:
4079:
4076:
4071:
4067:
4061:
4058:
4053:
4049:
4044:
4039:
4035:
4031:
4027:
4025:
4016:
4013:
4008:
4004:
3998:
3995:
3990:
3986:
3982:
3978:
3971:
3968:
3962:
3956:
3952:
3951:
3943:
3941:
3939:
3937:
3935:
3933:
3929:
3924:
3920:
3916:
3912:
3908:
3904:
3900:
3896:
3892:
3885:
3882:
3877:
3873:
3869:
3865:
3861:
3857:
3853:
3849:
3845:
3838:
3835:
3830:
3826:
3822:
3818:
3811:
3808:
3803:
3799:
3795:
3791:
3787:
3783:
3779:
3775:
3768:
3765:
3761:
3756:
3753:
3749:
3742:
3735:
3729:
3726:
3722:
3718:
3714:
3708:
3705:
3700:
3696:
3692:
3688:
3687:
3682:
3675:
3672:
3667:
3663:
3659:
3655:
3651:
3647:
3640:
3637:
3632:
3628:
3624:
3620:
3616:
3612:
3608:
3604:
3597:
3594:
3589:
3585:
3581:
3580:"Naphthalene"
3575:
3572:
3567:
3563:
3556:
3554:
3552:
3548:
3542:
3539:
3535:
3531:
3526:
3524:
3522:
3520:
3518:
3516:
3512:
3507:
3501:
3497:
3496:
3488:
3486:
3484:
3482:
3478:
3467:on 2016-03-04
3466:
3462:
3458:
3452:
3449:
3438:on 2016-03-04
3437:
3433:
3429:
3423:
3420:
3416:
3414:
3409:
3404:
3402:
3398:
3393:
3389:
3388:
3380:
3378:
3376:
3374:
3372:
3370:
3366:
3355:
3351:
3350:"naphthalene"
3344:
3342:
3340:
3336:
3331:
3325:
3321:
3317:
3313:
3312:
3304:
3302:
3300:
3298:
3296:
3294:
3292:
3290:
3288:
3286:
3284:
3282:
3280:
3278:
3274:
3259:
3253:
3251:
3249:
3245:
3240:
3234:
3226:
3220:
3216:
3212:
3208:
3204:
3198:
3195:
3189:
3186:
3180:
3175:
3172:
3170:
3166:
3163:
3161:
3158:
3156:
3153:
3151:
3147:
3143:
3140:
3138:
3135:
3134:
3130:
3124:
3121:
3120:
3116:
3113:
3110:
3107:
3104:
3094:
3091:
3090:
3086:
3083:
3080:
3077:
3074:
3063:
3061:
3058:
3057:
3053:
3050:
3047:
3044:
3041:
3030:
3028:
3025:
3024:
3020:
3017:
3014:
3011:
3008:
2997:
2995:
2992:
2991:
2987:
2984:
2981:
2978:
2975:
2964:
2962:
2959:
2958:
2954:
2951:
2948:
2945:
2942:
2928:
2925:
2924:
2921:
2919:
2917:160 (15 Torr)
2916:
2913:
2910:
2899:
2896:
2895:
2891:
2888:
2885:
2882:
2879:
2868:
2866:
2863:
2862:
2858:
2855:
2852:
2848:
2845:
2842:
2831:
2828:
2827:
2823:
2821:
2819:
2816:
2813:
2799:
2797:
2794:
2793:
2789:
2787:
2784:
2781:
2778:
2764:
2762:
2759:
2758:
2755:
2752:
2749:
2746:
2743:
2740:
2737:
2734:
2733:
2730:
2724:
2722:
2720:
2716:
2711:
2709:
2704:
2702:
2698:
2694:
2690:
2686:
2682:
2678:
2677:US government
2671:
2669:
2667:
2663:
2659:
2655:
2651:
2647:
2643:
2638:
2636:
2632:
2629:
2625:
2621:
2620:neuroblastoma
2617:
2613:
2609:
2604:
2602:
2598:
2594:
2590:
2586:
2582:
2578:
2574:
2570:
2566:
2562:
2558:
2552:
2544:
2542:
2540:
2536:
2528:
2526:
2524:
2520:
2516:
2512:
2507:
2505:
2501:
2497:
2495:
2491:
2487:
2482:
2480:
2479:agrichemicals
2476:
2468:
2464:
2460:
2453:
2451:
2449:
2445:
2441:
2437:
2433:
2429:
2424:
2422:
2418:
2413:
2411:
2407:
2402:
2400:
2396:
2392:
2388:
2384:
2380:
2376:
2368:
2366:
2364:
2360:
2356:
2352:
2344:
2342:
2340:
2336:
2332:
2328:
2321:
2317:
2313:
2309:
2301:
2299:
2297:
2293:
2289:
2285:
2281:
2277:
2273:
2269:
2265:
2257:
2255:
2253:
2251:
2246:
2238:
2236:
2234:
2233:
2228:
2227:
2222:
2218:
2214:
2210:
2206:
2202:
2197:
2195:
2191:
2183:
2181:
2179:
2175:
2171:
2167:
2163:
2159:
2155:
2154:North America
2150:
2148:
2144:
2140:
2136:
2132:
2128:
2124:
2120:
2116:
2112:
2108:
2104:
2098:
2096:
2092:
2088:
2079:
2072:
2070:
2068:
2064:
2060:
2020:
2019:
2018:
2016:
2012:
2008:
1991:
1968:
1964:
1939:
1935:
1930:
1915:
1907:
1905:
1904:derivatives.
1903:
1879:
1878:
1877:
1875:
1871:
1870:phenyllithium
1863:
1861:
1821:
1820:
1819:
1817:
1813:
1809:
1805:
1801:
1796:
1794:
1790:
1786:
1782:
1778:
1774:
1770:
1766:
1762:
1758:
1754:
1753:electrophilic
1746:
1741:
1739:
1737:
1733:
1729:
1725:
1721:
1714:
1710:
1706:
1699:
1695:
1691:
1688:
1684:
1676:
1674:
1672:
1664:
1662:
1658:
1654:
1646:
1642:
1636:
1632:
1631:
1630:
1628:
1624:
1620:
1615:
1607:
1603:
1602:
1601:
1599:
1595:
1591:
1587:
1583:
1579:
1575:
1571:
1562:
1560:
1557:
1552:
1550:
1546:
1542:
1538:
1530:
1528:
1526:
1522:
1518:
1514:
1510:
1506:
1502:
1498:
1494:
1486:
1484:
1482:
1478:
1474:
1470:
1466:
1462:
1449:
1438:
1434:with formula
1433:
1429:
1417:
1410:
1405:
1388:
1382:
1378:
1374:
1370:
1369:
1365:
1362:(Recommended)
1361:
1357:
1356:
1352:
1349:(Permissible)
1348:
1344:
1343:
1339:
1338:
1333:
1323:
1319:
1310:
1309:
1305:
1301:
1297:
1293:
1289:
1288:
1284:
1282:
1279:
1278:
1274:
1271:
1265:
1264:
1260:
1258:
1255:
1254:
1247:
1240:
1233:
1209:
1206:
1205:
1201:
1200:
1182:
1179:
1175:
1174:
1156:
1153:
1149:
1148:
1145:
1142:
1139:
1135:
1134:
1130:
1125:
1120:
1115:
1111:
1108:
1104:
1103:
1099:
1097:
1092:
1089:
1085:
1081:
1077:
1073:
1070:
1065:
1064:
1060:
1059:
1054:
1049:
1045:
1037:
1029:
1023:
1022:
1018:
1013:
1005:
1001:
1000:
997:78.53 kJ/mol
996:
988:
980:
974:
973:
969:
961:
956:
950:
949:
945:
940:
935:
934:Heat capacity
931:
930:
925:
917:
913:
909:
905:
902:
898:
897:
885:
882:
878:
877:
869:
866:
862:
861:
858:
855:
852:
848:
847:
842:
834:
832:
829:
828:
824:
817:
813:
809:
808:
796:
794:
791:
790:
786:
782:
778:
777:
773:
766:
762:
756:
755:
745:
743:
740:
739:
735:
733:
732:
727:
726:
718:
716:
712:
709:
708:
698:
696:
692:
689:
688:
678:
676:
672:
669:
668:
658:
656:
652:
649:
648:
638:
636:
632:
629:
628:
625:
621:
617:
610:
603:
596:
585:
581:
577:
573:
571:
568:
567:
555:
552:
548:
547:
541:
539:
538:Boiling point
536:
535:
527:
525:
524:Melting point
522:
521:
513:
511:
508:
507:
503:
501:
498:
497:
493:
490:
489:
482:
480:
477:
476:
461:
458:
454:
453:
448:
439:
435:
428:
414:
404:
400:
393:
385:
381:
380:DTXSID8020913
377:
376:
374:
364:
360:
359:
352:
348:
347:
345:
343:
340:
339:
332:
331:
329:
327:
324:
323:
316:
312:
311:
309:
303:
299:
298:
291:
287:
286:
284:
282:
279:
278:
274:
271:
267:
266:
259:
258:
256:
254:
249:
248:
244:
240:
237:
235:
233:ECHA InfoCard
230:
229:
222:
218:
217:
215:
213:
210:
209:
202:
198:
197:
195:
193:
190:
189:
182:
178:
177:
175:
173:
170:
169:
165:
162:
158:
157:
150:
146:
145:
143:
139:
134:
133:
126:
122:
121:
119:
116:
112:
111:
106:
98:
92:
88:
83:
79:
74:
70:
65:
54:
50:
44:
40:
39:
35:
27:
23:
19:
8037:Insecticides
8017:Naphthalenes
7952:
7935:Spectroscopy
7789:Astrobiology
7750:
7642:Formaldehyde
7534:Benzonitrile
7325:Acetaldehyde
7280:Methanethiol
7231:Acetonitrile
7136:Carbodiimide
7015:Formaldehyde
7010:Cyanoethynyl
6861:Iron cyanide
6856:Hydroperoxyl
6657:Nitric oxide
6398:Dicoronylene
6347:Anthanthrene
6271:
6229:Triphenylene
6214:Fluoranthene
6173:Phenanthrene
6148:Acenaphthene
6131:
6028:
5924:
5916:
5908:
5861:
5853:
5845:
5806:
5780:Pseudocumene
5744:Ethylbenzene
5725:
5717:
5709:
5640:Phenanthrene
5573:
5548:hydrocarbons
5423:Cycloheptyne
5413:Cyclopentyne
5403:Cyclopropyne
5395:Cycloalkynes
5312:Cycloheptene
5302:Cyclopentene
5292:Cyclopropene
5284:Cycloalkenes
5171:
5164:
5042:
5035:
5022:hydrocarbons
5003:Spiroalkanes
4833:Cycloheptane
4823:Cyclopentane
4813:Cyclopropane
4805:Cycloalkanes
4672:
4665:
4652:hydrocarbons
4641:Hydrocarbons
4600:
4585:
4544:
4539:
4528:. Retrieved
4523:
4513:
4502:. Retrieved
4493:
4481:
4469:. Retrieved
4457:
4445:
4433:. Retrieved
4429:
4420:
4408:. Retrieved
4404:
4395:
4387:
4379:
4360:
4330:December 25,
4328:. Retrieved
4313:
4307:
4295:. Retrieved
4291:the original
4286:
4277:
4264:
4260:
4233:
4229:
4219:
4209:December 11,
4207:. Retrieved
4200:
4191:
4154:
4150:
4140:
4123:
4117:
4111:
4094:
4088:
4078:
4070:the original
4060:
4033:
4030:Microbiology
4029:
4023:
4015:
4006:
3997:
3980:
3976:
3970:
3948:
3898:
3894:
3884:
3851:
3847:
3837:
3820:
3817:J. Org. Chem
3816:
3810:
3777:
3773:
3767:
3759:
3755:
3747:
3728:
3720:
3716:
3707:
3690:
3684:
3674:
3649:
3645:
3639:
3606:
3602:
3596:
3583:
3574:
3541:
3494:
3469:. Retrieved
3465:the original
3460:
3451:
3440:. Retrieved
3436:the original
3431:
3422:
3411:
3386:
3357:. Retrieved
3354:chemister.ru
3353:
3309:
3265:. Retrieved
3202:
3197:
3188:
2728:
2712:
2710:since 2008.
2705:
2675:
2639:
2605:
2554:
2532:
2515:beta blocker
2508:
2498:
2483:
2472:
2467:beta blocker
2440:formaldehyde
2425:
2414:
2403:
2372:
2355:plasticizers
2348:
2316:nitrobenzene
2312:benzonitrile
2305:
2261:
2249:
2242:
2230:
2224:
2198:
2187:
2151:
2103:distillation
2099:
2084:
2067:permanganate
2056:
1992:
1934:hydrogenated
1931:
1911:
1899:
1867:
1859:
1798:In terms of
1797:
1750:
1735:
1731:
1723:
1719:
1712:
1708:
1704:
1697:
1693:
1685:of about 10
1680:
1667:
1665:
1651:
1640:
1622:
1618:
1611:
1600:structures.
1594:ground state
1574:valence bond
1566:
1553:
1544:
1543:, rings are
1534:
1504:
1493:distillation
1490:
1427:
1426:
1336:
1303:
1268:Autoignition
1203:
1143:
1095:
1067:Main hazards
1056:
1035:
1011:
986:
959:
938:
915:
911:
907:
815:
764:
730:
715:butyric acid
544:at 760 mmHg
532:at 760 mmHg
326:RTECS number
108:Identifiers
100:Other names
32:Naphthalene
8022:Antiseptics
7909:Outer space
7819:Cosmic dust
7784:Abiogenesis
7696:Unconfirmed
7652:Heavy water
7492:Ethanethiol
7407:Cyanoallene
7397:Acetic acid
7367:Methylamine
7251:Diacetylene
7166:Formic acid
7156:Cyanomethyl
6814:Diazenylium
6804:CCP radical
6680:(molecular)
6664:(molecular)
6633:(molecular)
6372:Triangulene
6357:Corannulene
6265:Benzopyrene
6260:Benzopyrene
6255:Benzopyrene
6132:Naphthalene
5828:C4-Benzenes
5785:Hemellitene
5758:C3-Benzenes
5692:C2-Benzenes
5655:Corannulene
5574:Naphthalene
5438:Cyclodecyne
5433:Cyclononyne
5428:Cyclooctyne
5418:Cyclohexyne
5408:Cyclobutyne
5327:Cyclodecene
5322:Cyclononene
5317:Cyclooctene
5307:Cyclohexene
5297:Cyclobutene
5017:Unsaturated
4848:Cyclodecane
4843:Cyclononane
4838:Cyclooctane
4828:Cyclohexane
4818:Cyclobutane
4587:Naphthalene
4580:Naphthalene
4568:Naphthalene
4562:Naphthalene
4388:Physorg.com
4348:|work=
4236:(1): 42â7.
4182:1885/229663
4119:Tetrahedron
3652:: 209â221.
3534:Naphthalene
3408:Naphthalene
2741:Molar mass
2652:in humans,
2628:bronchiolar
2539:sublimation
2511:propranolol
2463:Propranolol
2421:surfactants
2363:alkyd resin
2335:DielsâAlder
2081:Naphthalene
1816:Sulfonation
1804:Sulfonation
1795:catalysts.
1683:resistivity
1539:rings. (In
1505:naphthaline
1499:. In 1821,
1469:ppm by mass
1428:Naphthalene
1318:median dose
1304:Lethal dose
1270:temperature
1257:Flash point
1138:Signal word
1078:, possible
1061:(OHS/OSH):
881:Point group
865:Space group
759:Henry's law
655:acetic acid
574:Soluble in
491:Appearance
450:Properties
239:100.001.863
201:ChEMBL16293
181:CHEBI:16482
94:Naphthalene
8011:Categories
7824:Cosmic ray
7766:Silylidyne
7729:Hemolithin
7704:Anthracene
7621:Deuterated
7602:Pyrimidine
7412:Ethanimine
7275:Ketenimine
7131:Butadiynyl
6955:Thioformyl
6809:Chloronium
6417:Hexa-cata-
6158:Anthracene
5887:Prehnitene
5775:Mesitylene
5630:Circulenes
5579:Anthracene
5507:Alkatriene
5476:Heptadiene
5466:Pentadiene
5456:Propadiene
5385:Norbornene
5255:Isoheptyne
5245:Isopentyne
5130:Isoheptene
5120:Isopentene
4942:Diamondoid
4937:Adamantane
4912:Norbornane
4776:Isoheptane
4766:Neopentane
4756:Isopentane
4530:2012-11-23
4504:2013-11-23
3471:2014-06-21
3461:DDBST GmbH
3442:2014-06-21
3432:DDBST GmbH
3359:2014-06-21
3267:2014-06-21
3181:References
3169:2-Naphthol
3165:1-Naphthol
2865:1-Naphthol
2695:has set a
2687:has set a
2672:Regulation
2529:Other uses
2519:nabumetone
2500:Alkylation
2387:pesticides
2383:2-naphthol
2379:1-naphthol
2331:anthracene
2221:endophytic
2178:Kazakhstan
2166:metallurgy
2113:to remove
2073:Production
2069:reagents.
2045:O + 2 CO
1864:Lithiation
1718:(멉
m) and
1711:)), where
1590:conjugated
1525:Carl GrÀbe
1107:Pictograms
1080:carcinogen
1076:sensitizer
1028:combustion
857:Monoclinic
844:Structure
711:Solubility
691:Solubility
675:chloroform
671:Solubility
651:Solubility
631:Solubility
570:Solubility
479:Molar mass
351:2166IN72UN
212:ChemSpider
136:3D model (
115:CAS Number
91:IUPAC name
7756:Phosphine
7624:molecules
7557:fullerene
7457:Acetamide
7261:Formamide
7141:Cyanamide
6995:Acetylene
6970:Tricarbon
6881:Methylene
6866:Isoformyl
6771:Triatomic
6544:Molecules
6494:Phenacene
6484:Cyclacene
6479:Circulene
6408:Heptacene
6316:Pentacene
6224:Tetracene
6168:Phenalene
6056:Annulynes
6051:Annulenes
5892:Isodurene
5625:Helicenes
5599:Heptacene
5589:Pentacene
5584:Tetracene
5512:Alkadiyne
5491:Decadiene
5486:Nonadiene
5481:Octadiene
5471:Hexadiene
5461:Butadiene
5270:Isodecyne
5265:Isononyne
5260:Isooctyne
5250:Isohexyne
5145:Isodecene
5140:Isononene
5135:Isooctene
5125:Isohexene
5115:Isobutene
5020:aliphatic
4977:Churchane
4972:Basketane
4791:Isodecane
4786:Isononane
4781:Isooctane
4771:Isohexane
4751:Isobutane
4650:aliphatic
4648:Saturated
4350:ignored (
4340:cite book
3923:0031-9007
3876:0021-9606
3760:Blue Book
3320:CRC Press
3233:cite book
3160:Mothballs
2650:cataracts
2573:confusion
2284:pesticide
2268:mothballs
2201:magnolias
2091:petroleum
2059:Oxidation
1938:catalysts
1896:Li + BuBr
1773:alkylated
1755:aromatic
1598:resonance
1501:John Kidd
1481:mothballs
1098:labelling
1084:explosive
1072:Flammable
979:formation
953:Std molar
831:Viscosity
578:, liquid
333:QJ0525000
260:214-552-7
252:EC Number
22:naphthene
7743:Linear C
7724:Graphene
7636:Ammonium
7437:Acrolein
7300:Propynal
7285:Methanol
7256:Ethylene
7125:Ammonium
6900:Nitroxyl
6724:Sulfanyl
6668:Imidogen
6662:Nitrogen
6631:Hydrogen
6576:Argonium
6553:Diatomic
6489:Helicene
6443:Sumanene
6433:Rubicene
6423:Kekulene
6393:Coronene
6386:7+ rings
6377:Zethrene
6367:Hexacene
6321:Perylene
6209:Chrysene
6163:Fluorene
6122:Butalene
5660:Kekulene
5645:Chrysene
5635:Butalene
5620:Fluorene
5594:Hexacene
5546:Aromatic
5517:Cumulene
4987:Twistane
4982:Pagodane
4962:Prismane
4498:Archived
4462:Archived
4368:Archived
4297:March 6,
4252:10894241
4052:12427963
4007:Sci/Tech
3802:96765335
3741:Archived
3666:97798085
3631:36525625
3590:(NIOSH).
3568:(NIOSH).
3146:Tetralin
3131:See also
2849:190 (35
2750:Density
2646:Group 2B
2631:adenomas
2624:alveolar
2597:jaundice
2585:diarrhea
2581:vomiting
2494:solvents
2486:tetralin
2475:azo dyes
2436:concrete
2428:polymers
2296:opossums
2280:fumigant
2264:fumigant
2258:Fumigant
2217:nematode
2194:creosote
2190:homologs
2137:(0.2%),
2087:coal tar
2063:chromate
2029:+ 4.5 O
2011:catalyst
1963:tetralin
1789:sulfuric
1787:, using
1785:alcohols
1763:to give
1761:catalyst
1582:aromatic
1497:coal tar
1473:aromatic
1471:. As an
1379:250 ppm
1204:NFPA 704
1051:Hazards
783:(χ)
761:constant
576:alcohols
166:1421310
26:Naphtali
7889:Kerogen
7776:Related
7719:Glycine
7672:Propyne
7631:Ammonia
7529:Benzene
7524:Acetone
7516:or more
7487:Propene
7472:Ethanol
7362:Propyne
7181:Methane
7050:Ketenyl
7000:Ammonia
6458:Truxene
6438:Rubrene
6428:Ovalene
6340:6 rings
6243:5 rings
6182:4 rings
6141:3 rings
6127:Azulene
6115:2 rings
6013:Benzene
5987:Styrene
5864:-Cymene
5856:-Cymene
5848:-Cymene
5837:Cymenes
5728:-Xylene
5720:-Xylene
5712:-Xylene
5701:Xylenes
5682:Toluene
5615:Azulene
5214:Heptyne
5204:Pentyne
5194:Propyne
5159:Alkynes
5084:Heptene
5074:Pentene
5064:Propene
5030:Alkenes
4952:Sterane
4918:Decalin
4906:Housane
4720:Heptane
4710:Pentane
4700:Propane
4690:Methane
4660:Alkanes
4471:6 March
4458:Epa.gov
4435:6 March
4430:Cdc.gov
4159:Bibcode
4157:: 389.
3903:Bibcode
3856:Bibcode
3782:Bibcode
3623:6376602
3562:"#0439"
3150:Decalin
3137:Camphor
3117:
2859:1.6552
2719:camphor
2658:rabbits
2633:of the
2616:adenoma
2606:The US
2591:in the
2569:fatigue
2490:decalin
2302:Solvent
2292:insects
2252:-xylene
2223:fungus
2174:Ukraine
2158:Koppers
2119:phenols
1967:decalin
1781:alkenes
1730:), and
1657:azulene
1648:Azulene
1627:isomers
1551:(PAH).
1537:benzene
1517:benzene
1509:naphtha
1487:History
1477:benzene
1409:what is
1407: (
1007:(Δ
955:entropy
825:1.5898
797:98 kPa:
763: (
635:ethanol
624:aniline
620:toluene
580:ammonia
510:Density
484:128.174
302:PubChem
125:91-20-3
18:naphtha
7940:Tholin
7761:Pyrene
7206:Silane
7176:Ketene
6678:Oxygen
6326:Picene
6219:Pyrene
5882:Durene
5801:Cumene
5650:Pyrene
5566:Acenes
5448:Dienes
5229:Decyne
5224:Nonyne
5219:Octyne
5209:Hexyne
5199:Butyne
5189:Ethyne
5099:Decene
5094:Nonene
5089:Octene
5079:Hexene
5069:Butene
5059:Ethene
4957:Cubane
4735:Decane
4730:Nonane
4725:Octane
4715:Hexane
4705:Butane
4695:Ethane
4410:24 May
4321:
4250:
4050:
3957:
3921:
3874:
3800:
3664:
3629:
3621:
3502:
3326:
3221:
3142:Dialin
3105:170.25
3087:1.670
3075:207.07
3054:1.643
3042:162.62
3021:1.632
3009:162.62
2988:1.593
2976:146.16
2943:173.17
2911:156,18
2880:144,17
2843:190.63
2814:172.18
2779:172.18
2660:, and
2595:, and
2577:nausea
2517:) and
2415:Alkyl
2320:durene
2170:Russia
2139:indene
2135:indane
2115:acidic
2049:+ 2 H
2013:gives
1775:using
1430:is an
1404:verify
1401:
1144:Danger
695:hexane
434:SMILES
290:C00829
192:ChEMBL
85:Names
7926:(PAH)
7514:atoms
7449:atoms
7389:atoms
7387:Eight
7317:atoms
7315:Seven
7223:atoms
7117:atoms
6987:atoms
6975:Water
6905:Ozone
6847:(HNC)
6841:(HCN)
6474:Acene
6044:Other
6029:trans
6006:Other
5945:Other
5901:Other
5794:Other
5737:Other
5608:Other
5532:Enyne
5500:Other
4996:Other
4465:(PDF)
4454:(PDF)
3798:S2CID
3744:(PDF)
3737:(PDF)
3662:S2CID
3627:S2CID
3394:â446.
3261:(PDF)
3114:0.987
3084:1.489
3051:1.138
3018:1.194
2985:1.323
2946:53â57
2889:1.224
2883:94â96
2856:1.265
2846:16â19
2817:185.5
2715:China
2601:liver
2593:urine
2589:blood
2473:Many
2465:is a
2373:Many
2329:with
2288:attic
2286:, in
2276:moths
2123:basic
2033:â C
1916:, NaC
1851:H + H
1619:alpha
1586:diene
1556:IUPAC
1545:fused
1337:NIOSH
1294:(TLV)
1285:5.9%
736:3.34
399:InChI
275:3347
172:ChEBI
138:JSmol
24:, or
7447:Nine
7115:Five
7025:HCCN
6985:Four
6945:SiNC
5925:tert
5557:PAHs
4473:2022
4437:2022
4412:2013
4352:help
4332:2008
4319:ISBN
4299:2005
4248:PMID
4211:2021
4048:PMID
3955:ISBN
3919:ISSN
3872:ISSN
3619:PMID
3500:ISBN
3324:ISBN
3239:link
3219:ISBN
3045:59.5
2952:1.22
2851:Torr
2735:Name
2662:mice
2654:rats
2640:The
2635:lung
2626:and
2618:and
2430:are
2410:dyes
2404:The
2381:and
2357:for
2318:and
2239:Uses
2215:and
2205:deer
2041:(CO)
1767:and
1703:exp(
1623:beta
1373:IDLH
1196:P501
1192:P281
1188:P273
1184:P210
1170:H410
1166:H351
1162:H302
1158:H228
729:log
500:Odor
342:UNII
281:KEGG
7738:NCO
7638:ion
7545:, C
7512:Ten
7221:Six
7127:ion
5917:sec
5174:â 2
4675:+ 2
4238:doi
4177:hdl
4167:doi
4128:doi
4099:doi
4038:doi
4034:148
3985:doi
3911:doi
3864:doi
3825:doi
3790:doi
3778:258
3721:149
3695:doi
3691:137
3654:doi
3650:111
3611:doi
3392:443
3211:doi
3111:128
3108:143
3081:279
3048:256
3015:259
2982:215
2979:â19
2949:340
2914:1â2
2886:278
2840:ClO
2785:300
2782:157
2713:In
2603:).
2525:).
2521:(a
2513:(a
2446:or
2399:CFT
2339:DDQ
2152:In
2065:or
2009:as
1990:).
1839:â C
1831:+ C
1791:or
1783:or
1751:In
1495:of
1360:REL
1347:PEL
1096:GHS
1088:air
1039:298
990:298
963:298
874:/b
713:in
693:in
673:in
653:in
633:in
606:CCl
368:EPA
315:931
305:CID
221:906
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7555:70
7547:60
7543:60
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7266:HC
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588:C
472:8
469:H
463:C
370:)
366:(
140:)
28:.
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