3146:
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94:
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1726:
Cases of acetonitrile poisoning in humans (or, to be more specific, of cyanide poisoning after exposure to acetonitrile) are rare but not unknown, by inhalation, ingestion and (possibly) by skin absorption. The symptoms, which do not usually appear for several hours after the exposure, include
1435:
including butadiene, and as the acetonitrile falls down through the column, it absorbs the butadiene which is then sent from the bottom of the tower to a second separating tower. Heat is then employed in the separating tower to separate the butadiene.
2436:
B. Swanson, D. F. Shriver, J. A. Ibers, "Nature of the donor-acceptor bond in acetonitrile-boron trihalides. The structures of the boron trifluoride and boron trichloride complexes of acetonitrile", Inorg. Chem., 2969., volume 8, pp. 2182-2189,
1963:
The metabolism of acetonitrile is much slower than that of other nitriles, which accounts for its relatively low toxicity. Hence, one hour after administration of a potentially lethal dose, the concentration of cyanide in the rat brain was
2447:
Haiges, Ralf; Baxter, Amanda F.; Goetz, Nadine R.; Axhausen, Joachim A.; Soltner, Theresa; Kornath, Andreas; Christe, Kalr O. (2016). "Protonation of nitriles: isolation and characterization of alkyl- and arylnitrilium ions".
878:
845:
2739:"Twenty-Fifth Commission Directive 2000/11/EC of 10 March 2000 adapting to technical progress Annex II to Council Directive 76/768/EEC on the approximation of laws of the Member States relating to cosmetic products"
1723:, which is the source of the observed toxic effects. Generally the onset of toxic effects is delayed, due to the time required for the body to metabolize acetonitrile to cyanide (generally about 2–12 hours).
1658:. Most is combusted to support the intended process but an estimated several thousand tons are retained for the above-mentioned applications. Production trends for acetonitrile thus generally follow those of
2910:
978:
936:
2144:
2119:
1116:
1301:
2598:
1609:
2607:
2594:
2313:
1770:, despite its toxicity. At least two cases have been reported of accidental poisoning of young children by acetonitrile-based nail polish remover, one of which was fatal.
2485:
1989:
pathway). It also allows more of the acetonitrile to be excreted unchanged before it is metabolised. The main pathways of excretion are by exhalation and in the urine.
4159:
4079:
3895:
3830:
3770:
3698:
3604:
3498:
3368:
2919:
2799:
Pozzani, U. C.; Carpenter, C. P.; Palm, P. E.; Weil, C. S.; Nair, J. H. (1959), "An investigation of the mammalian toxicity of acetonitrile",
963:
2903:
2095:
4420:
971:
2689:
47:
2743:
478:
1464:
2874:
2704:
1662:. Acetonitrile can also be produced by many other methods, but these are of no commercial importance as of 2002. Illustrative routes are by dehydration of
1447:
with water and a range of organic solvents, but not saturated hydrocarbons. It has a convenient range of temperatures at which it is a liquid, and a high
2896:
2653:
2196:
1702:
and its production also decreased, further compounding the acetonitrile shortage. The global shortage of acetonitrile continued through early 2009.
985:
1498:
1460:
814:
928:
2079:
1572:
787:
662:
2853:
1981:
The relatively slow metabolism of acetonitrile to hydrogen cyanide allows more of the cyanide produced to be detoxified within the body to
4282:
2502:
1564:
2161:
4400:
4182:
2621:
2615:
2413:
2389:
453:
67:
37:
2330:
4307:
1695:
2521:, Olive, G. & Olive, S., "Process for preparing acetonitrile", published 1979-12-18, assigned to
2548:
2702:
Caravati, E. M.; Litovitz, T. (1988). "Pediatric cyanide intoxication and death from an acetonitrile-containing cosmetic".
77:
4232:
932:
4267:
1308:
1686:
Starting in
October 2008, the worldwide supply of acetonitrile was low because Chinese production was shut down for the
922:
386:
2738:
3463:
417:
1903:
Ionic cyanide concentrations measured in the brains of
Sprague-Dawley rats one hour after oral administration of an
869:
2877:, on: SciTechDaily. September 10, 2020. Source: Tokyo University of Science: Acetonitrile found in molecular cloud
2309:
2063:
1509:
1140:
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644:
4222:
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301:
4262:
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3418:
1544:
1270:
1008:
331:
3619:
3594:
3584:
864:
4405:
4342:
1778:
are often preferred as safer for domestic use, and acetonitrile has been banned in cosmetic products in the
688:
337:
289:
4197:
3990:
3318:
3259:
3167:
3162:
3072:
2949:
2944:
1779:
1452:
763:
3323:
2994:
2349:"Synthesis of α,β-Unsaturated Nitriles from Acetonitrile: Cyclohexylideneacetonitrile and Cinnamonitrile"
1459:, acetonitrile dissolves a wide range of ionic and nonpolar compounds and is useful as a mobile phase in
4252:
4227:
3865:
3624:
3483:
3468:
3438:
3030:
2765:
Ahmed, A. E.; Farooqui, M. Y. H. (1982), "Comparative toxicities of aliphatic nitriles",
2544:
2279:
2009:
1998:
1471:
1378:
892:
857:
599:
251:
118:
3554:
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3579:
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4297:
3922:
3293:
3264:
3145:
2969:
2540:
106:
3217:
1694:. Due to the global economic slowdown, the production of acrylonitrile used in acrylic fibers and
4257:
4237:
4050:
3740:
3574:
3228:
3092:
3067:
3035:
2954:
2060:
Nomenclature of
Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)
1767:
1744:
1494:
1448:
1428:
1412:
1243:
434:
165:
3244:
2212:"Molecular Structures of Hydrogen Cyanide and Acetonitrile as Studied by Gas Electron Diffraction"
4355:
4277:
4247:
4192:
4069:
4045:
3790:
3544:
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3343:
3303:
3187:
3154:
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1904:
1800:
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1479:
1347:
1228:
211:
3338:
3249:
2875:
How Did
Organic Matter Reach Earth? Cosmic Detectives Trace Origin of Complex Organic Molecules
2408:. Li, Guangtao, Dr. (3rd, completely rev. and enl. ed.). Weinheim: Wiley-VCH. p. 26.
4410:
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1748:
1639:
1548:
1532:
1520:
1382:
1332:
1208:
1203:
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1952:. The glycolonitrile then undergoes a spontaneous decomposition to give hydrogen cyanide and
4415:
4379:
4367:
4287:
4187:
4117:
4092:
4040:
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3348:
3313:
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1946:
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1021:
320:
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applications because of its relatively high dielectric constant and ability to dissolve
438:
293:
231:
175:
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1938:
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1440:
1279:
1213:
623:
612:
20:
2483:
Pollak, Peter; Romeder, Gérard; Hagedorn, Ferdinand; Gelbke, Heinz-Peter. "Nitriles".
1678:. In 1992, 14,700 tonnes (16,200 short tons) of acetonitrile were produced in the US.
4394:
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3443:
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1949:
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3725:
3708:
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3519:
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3192:
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1953:
2835:
898:
2866:, Office of Pollution Prevention and Toxics, U.S. Environmental Protection Agency
359:
4292:
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3780:
3750:
3634:
3549:
3539:
3269:
3197:
2680:
2348:
2071:
1982:
1957:
1563:
Acetonitrile has a free electron pair at the nitrogen atom, which can form many
1475:
1444:
1432:
1401:
1104:
1078:
1045:
997:
4207:
4149:
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910:
4139:
4004:
3840:
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3524:
3378:
3353:
2882:
2423:
2136:
1986:
1956:. Formaldehyde, a toxin and a carcinogen on its own, is further oxidized to
1937:
in 1959. The first step in this pathway is the oxidation of acetonitrile to
1926:
1663:
1643:
1490:
1486:
1424:
1386:
906:
406:
2863:
2820:
2469:
2786:
2724:
1698:(ABS) resins decreased. Acetonitrile is a byproduct in the production of
4107:
4019:
3820:
3683:
3668:
3639:
3508:
3283:
3107:
3051:
3045:
3014:
2959:
2927:
2005:
1540:
1405:
1218:
984:
977:
970:
943:
2228:
2211:
93:
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4102:
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3564:
3514:
3393:
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3136:
2461:
1918:
1771:
1675:
1631:
groups in these complexes are rapidly displaced by many other ligands.
1366:
1358:
557:
346:
302:
1504:
Acetonitrile plays a significant role as the dominant solvent used in
4323:
4144:
4126:
3589:
3559:
3061:
1752:
1732:
1568:
727:
242:
1278:
Except where otherwise noted, data are given for materials in their
902:
582:
81.3 to 82.1 °C; 178.2 to 179.7 °F; 354.4 to 355.2 K
1427:
in refineries. Specifically, acetonitrile is fed into the top of a
3358:
3288:
2322:
1942:
1456:
1258:
914:
370:
222:
198:
188:
51:
Skeletal formula of acetonitrile with all explicit hydrogens added
2247:[Action of anhydrous phosphoric acid on ammonium salts].
2245:"Action de l'acide phosphorique anhydre sur les sels ammoniacaux"
1740:
1715:
Acetonitrile has only modest toxicity in small doses. It can be
1423:
Acetonitrile is used mainly as a solvent in the purification of
1153:
547:
2892:
2210:
Karakida, Ken'ichi; Fukuyama, Tsutomu; Kuchitsu, Kozo (1974).
1411:
Acetonitrile was first prepared in 1847 by the French chemist
2141:
Immediately
Dangerous to Life or Health Concentrations (IDLH)
1515:
Industrially, it is used as a solvent for the manufacture of
422:
76:
66:
46:
36:
2347:
DiBiase, S. A.; Beadle, J. R.; Gokel, G. W.
2169:
Ashford's
Dictionary of Industrial Chemicals, Third edition
1690:. Furthermore, a U.S. factory was damaged in Texas during
572:−46 to −44 °C; −51 to −47 °F; 227 to 229 K
955:
2384:, vol. 1 (2nd ed.), Elsevier, pp. 28–30,
1296:
2854:
National
Pollutant Inventory - Acetonitrile fact sheet
1531:
Acetonitrile is a common two-carbon building block in
2145:
National
Institute for Occupational Safety and Health
2120:
National
Institute for Occupational Safety and Health
2600:
Fiche toxicologique no. 104 : Acétonitrile
2595:
Institut national de recherche et de sécurité (INRS)
1789:
1654:
Acetonitrile is a byproduct from the manufacture of
16:
Organic compound (CH3−C≡N); Simplest organic nitrile
4158:
4078:
4003:
3894:
3829:
3769:
3697:
3603:
3497:
3367:
3153:
2935:
2926:
2864:
Chemical
Summary for Acetonitrile (CAS No. 75-05-8)
1763:among the most commonly used emergency treatments.
1743:can occur in serious cases, followed by death from
1610:
tetrakis(acetonitrile)copper(I) hexafluorophosphate
1567:. Being weakly basic, it is an easily displaceable
1478:. For similar reasons, it is a popular solvent in
1439:In the laboratory, it is used as a medium-polarity
1357:. This colourless liquid is the simplest organic
358:
2659:Environmental Health Criteria 154. Acetonitrile
959:
174:
2486:Ullmann's Encyclopedia of Industrial Chemistry
2375:
2373:
2371:
2904:
2406:Organic synthesis : concepts and methods
2329:, Special Publication I.01.65, archived from
8:
2744:Official Journal of the European Communities
2315:Acetonitrile. Summary Risk Assessment Report
1646:, it is possible to protonate acetonitrile.
1016:523.0 °C (973.4 °F; 796.1 K)
2094:: CS1 maint: DOI inactive as of May 2024 (
2054:
2052:
1373:). It is produced mainly as a byproduct of
2932:
2911:
2897:
2889:
2760:
2758:
2654:International Programme on Chemical Safety
2036:"Material Safety Data Sheet: Acetonitrile"
1634:It also forms Lewis adducts with group 13
437:
292:
270:
25:
2227:
2216:Bulletin of the Chemical Society of Japan
2156:
2154:
1002:2.0 °C (35.6 °F; 275.1 K)
394:
2114:NIOSH Pocket Guide to Chemical Hazards.
1796:Cyanide, concentration in brain (μg/kg)
1626:
1618:
1614:
1601:
1597:
1593:
1589:
1585:
1352:
1341:
2849:International Chemical Safety Card 0088
2589:
2587:
2585:
2562:A. Tullo (2008). "A Solvent Dries Up".
2266:Steiner, P. A.; Gordy, W. (1966).
2109:
2107:
2105:
2030:
2028:
2026:
2024:
2020:
2001:– a derivative of acetonitrile used to
1960:, which is another source of toxicity.
1575:is prepared by heating a suspension of
483:
458:
433:
336:
2859:NIOSH Pocket Guide to Chemical Hazards
2674:
2672:
2648:
2646:
2644:
2642:
2640:
2288:
2277:
2195:: CS1 maint: archived copy as title (
2188:
2131:
2129:
2087:
1929:, especially in the liver, to produce
1499:high-performance liquid chromatography
283:
4421:Organic compounds with 2 carbon atoms
2304:
2302:
1766:It has been used in formulations for
1573:bis(acetonitrile)palladium dichloride
465:Key: WEVYAHXRMPXWCK-UHFFFAOYSA-N
250:
230:
7:
2690:U.S. Environmental Protection Agency
2682:Toxicological Review of Acetonitrile
2008:, and also used as a reagent in the
1535:of many useful chemicals, including
71:Ball and stick model of acetonitrile
2268:"Journal of Molecular Spectroscopy"
349:
4283:Nexus for Exoplanet System Science
1682:Acetonitrile shortage in 2008–2009
1565:transition metal nitrile complexes
14:
4183:Atomic and molecular astrophysics
2920:Molecules detected in outer space
2545:"The Great Acetonitrile Shortage"
2404:Jürgen-Hinrich., Fuhrhop (2003).
1978:dose 60 times lower (see table).
4373:
4361:
4349:
4338:
4337:
3144:
3135:
3126:
2813:10.1097/00043764-195912000-00003
1933:, as was first shown by Pozzani
1286:
868:
863:
519:
513:
92:
41:Skeletal formula of acetonitrile
4308:Polycyclic aromatic hydrocarbon
2564:Chemical & Engineering News
1696:acrylonitrile butadiene styrene
1282:(at 25 °C , 100 kPa).
81:Spacefill model of acetonitrile
2549:Science Translational Medicine
2064:The Royal Society of Chemistry
1365:is a simpler nitrile, but the
507:
1:
4233:Extraterrestrial liquid water
1727:breathing difficulties, slow
1497:make it a popular choice for
1485:Its ultraviolet transparency
1377:manufacture. It is used as a
1121:(US health exposure limits):
2779:10.1016/0378-4274(82)90179-5
2171:. p. 76. Archived from
1893:
1880:
1867:
1854:
1841:
1828:
1815:
3464:Protonated hydrogen cyanide
2437:{{doi:10.1021/ic50080a032}}
2380:Philip Wexler, ed. (2005),
2072:10.1039/9781849733069-FP001
1896:
1883:
1870:
1857:
1844:
1831:
1818:
1510:nucleoside phosphoramidites
1385:and in the purification of
1085:5655 ppm (guinea pig, 4 hr)
1034:or concentration (LD, LC):
835:−1256.03 – −1256.63 kJ/mol
617:9.71 kPa (at 20.0 °C)
62:
32:
4437:
2870:Simulation of acetonitrile
2382:Encyclopedia of Toxicology
2363:, vol. 7, p. 108
2310:Spanish Ministry of Health
1747:. The treatment is as for
462:InChI=1S/C2H3N/c1-2-3/h1H3
18:
4332:
4223:Earliest known life forms
4218:Diffuse interstellar band
3689:Protonated cyanoacetylene
3459:Protonated carbon dioxide
3419:Hydromagnesium isocyanide
3124:
2664:World Health Organization
2576:10.1021/cen-v086n047.p027
2327:European Chemicals Bureau
1901:
1559:As an electron pair donor
1537:acetamidine hydrochloride
1506:oligonucleotide synthesis
1276:
1269:
1264:
1164:
1115:
1030:
844:
839:
737:
494:
474:
449:
158:
129:
117:
105:
100:
91:
61:
31:
4401:Hazardous air pollutants
4268:Iron–sulfur world theory
4263:Photodissociation region
3966:Methyl-cyano-diacetylene
2717:10.1001/jama.260.23.3470
2679:Greenberg, Mark (1999),
2495:10.1002/14356007.a17_363
1786:Metabolism and excretion
1545:1-naphthaleneacetic acid
1369:anion is not classed as
1271:Acetonitrile (data page)
1265:Supplementary data page
1089:53,000 ppm (rat, 30 min)
923:Precautionary statements
552:Faint, distinct, fruity
19:Not to be confused with
4343:Category:Astrochemistry
3933:, fullerene, buckyball)
3620:Cyanobutadiynyl radical
3595:Silicon-carbide cluster
3585:Protonated formaldehyde
2489:. Weinheim: Wiley-VCH.
2074:(inactive 2024-05-06).
1111:16,000 ppm (dog, 4 hr)
1093:2693 ppm (mouse, 1 hr)
1087:2828 ppm (rabbit, 4 hr)
689:Magnetic susceptibility
4356:Outer space portal
4198:Circumstellar envelope
3163:Aluminium(I) hydroxide
3073:Phosphorus mononitride
2950:Aluminium monofluoride
2945:Aluminium monochloride
2287:Cite journal requires
1921:, acetonitrile can be
1780:European Economic Area
1171:Related alkanenitriles
966:
82:
72:
52:
42:
4253:Interplanetary medium
4228:Extraterrestrial life
3866:Octatetraynyl radical
3484:Tricarbon monosulfide
3031:Magnesium monohydride
2243:Dumas, J.-B. (1847).
2066:. 2014. p. 902.
2010:Overman rearrangement
1999:Trichloroacetonitrile
1917:In common with other
1608:A related complex is
1470:It is widely used in
1379:polar aprotic solvent
1147:TWA 20 ppm (34 mg/m)
1134:TWA 40 ppm (70 mg/m)
965:
119:Systematic IUPAC name
80:
70:
50:
40:
4380:Chemistry portal
4368:Astronomy portal
4314:RNA world hypothesis
4298:PAH world hypothesis
3991:Heptatrienyl radical
3923:Buckminsterfullerene
3811:Methylcyanoacetylene
3319:Silicon carbonitride
3294:Methylidynephosphane
3260:Magnesium isocyanide
3168:Aluminium isocyanide
2970:Carbon monophosphide
2751:: 22–25. 2000-03-14.
1910:of various nitriles.
1868:400 ± 100
1855:600 ± 200
1842:400 ± 100
1816:700 ± 200
1547:. Its reaction with
1323:, often abbreviated
1091:7500 ppm (rat, 8 hr)
1079:median concentration
948:(fire diamond)
107:Preferred IUPAC name
4258:Interstellar medium
4238:Forbidden mechanism
4051:Hydrogen isocyanide
3741:Hexatriynyl radical
3324:c-Silicon dicarbide
3229:Hydrogen isocyanide
3093:Silicon monosulfide
3068:Phosphorus monoxide
3036:Methylidyne radical
2995:Fluoromethylidynium
2955:Aluminium(II) oxide
2450:Dalton Transactions
2229:10.1246/bcsj.47.299
1829:510 ± 80
1768:nail polish remover
1745:respiratory failure
1495:chemical reactivity
1449:dielectric constant
1429:distillation column
1413:Jean-Baptiste Dumas
1244:Acetone cyanohydrin
808:40.16–40.96 kJ/mol
589:Solubility in water
562:0.786 g/cm at 25°C
534: g·mol
212:Beilstein Reference
141:Methanecarbonitrile
28:
4278:Molecules in stars
4248:Intergalactic dust
4193:Circumstellar dust
4135:Naphthalene cation
4070:Trihydrogen cation
4046:Hydrogen deuteride
3971:Methyltriacetylene
3806:Hexapentaenylidene
3625:E-Cyanomethanimine
3545:Cyclopropenylidene
3479:Tricarbon monoxide
3469:Silicon tricarbide
3439:Methylene amidogen
3429:Isothiocyanic acid
3344:Thioxoethenylidene
3304:Trihydrogen cation
3118:Titanium(II) oxide
3078:Potassium chloride
3057:Sulfur mononitride
3000:Helium hydride ion
2975:Carbon monosulfide
2836:WebBook page for C
2705:J. Am. Med. Assoc.
2688:, Washington, DC:
2462:10.1039/C6DT01301E
1782:since March 2000.
1761:sodium thiosulfate
1577:palladium chloride
1480:cyclic voltammetry
1309:Infobox references
1229:Aminopropionitrile
1165:Related compounds
1156:(Immediate danger)
967:
83:
73:
53:
43:
26:
4388:
4387:
4303:Pseudo-panspermia
3999:
3998:
3946:Cyanodecapentayne
3886:N-Methylformamide
3861:Methyldiacetylene
3786:Aminoacetonitrile
3756:Methyl isocyanate
3674:Methyl isocyanide
3555:Isocyanoacetylene
3535:Cyanoformaldehyde
3414:Hydrogen peroxide
3299:Potassium cyanide
3255:Magnesium cyanide
3208:Disilicon carbide
3203:Dicarbon monoxide
3010:Hydrogen fluoride
3005:Hydrogen chloride
2881:at the center of
2456:(20): 8494–8499.
2361:Collected Volumes
2354:Organic Syntheses
2323:Ispra (VA), Italy
2081:978-0-85404-182-4
1915:
1914:
1911:
1890:Table salt (NaCl)
1881:28 ± 5
1812:Potassium cyanide
1749:cyanide poisoning
1640:boron trifluoride
1579:in acetonitrile:
1549:cyanogen chloride
1533:organic synthesis
1527:Organic synthesis
1521:photographic film
1383:organic synthesis
1333:chemical compound
1317:Chemical compound
1315:
1314:
1254:Related compounds
1209:Aminoacetonitrile
1204:Cyanogen fluoride
1199:Cyanogen chloride
1064:
1058:
893:Hazard statements
781:149.62 J/(K·mol)
639:530 μmol/(Pa·kg)
542:Colorless liquid
418:CompTox Dashboard
200:Interactive image
87:
86:
57:
56:
4428:
4378:
4377:
4376:
4366:
4365:
4364:
4354:
4353:
4352:
4341:
4340:
4288:Organic compound
4188:Chemical formula
4093:Dihydroxyacetone
4041:Hydrogen cyanide
3726:Cyanodiacetylene
3580:Propadienylidene
3474:Thioformaldehyde
3349:Titanium dioxide
3314:Sodium hydroxide
3235:Hydrogen sulfide
3223:Hydrogen cyanide
3183:Carbonyl sulfide
3148:
3139:
3130:
3088:Silicon monoxide
3021:Hydroxyl radical
2933:
2913:
2906:
2899:
2890:
2824:
2823:
2796:
2790:
2789:
2762:
2753:
2752:
2735:
2729:
2728:
2699:
2693:
2692:
2687:
2676:
2667:
2666:
2650:
2635:
2634:
2633:
2632:
2626:
2620:, archived from
2605:
2591:
2580:
2579:
2559:
2553:
2552:
2537:
2531:
2530:
2529:
2525:
2523:Monsanto Company
2515:
2509:
2508:
2480:
2474:
2473:
2444:
2438:
2434:
2428:
2427:
2401:
2395:
2394:
2377:
2366:
2364:
2357:
2344:
2338:
2337:
2335:
2320:
2306:
2297:
2296:
2290:
2285:
2283:
2275:
2263:
2257:
2256:
2240:
2234:
2233:
2231:
2207:
2201:
2200:
2194:
2186:
2184:
2183:
2177:
2166:
2158:
2149:
2148:
2133:
2124:
2123:
2111:
2100:
2099:
2093:
2085:
2056:
2047:
2046:
2040:
2032:
1973:
1972:
1968:
1931:hydrogen cyanide
1902:
1790:
1735:, and vomiting.
1721:hydrogen cyanide
1630:
1622:
1604:
1451:of 38.8. With a
1443:solvent that is
1400:
1392:
1363:hydrogen cyanide
1356:
1345:
1299:
1293:
1290:
1289:
1194:Cyanogen bromide
1179:Hydrogen cyanide
1105:lowest published
1062:
1057:(dermal, rabbit)
1056:
1022:Explosive limits
987:
980:
973:
958:
938:
934:
930:
916:
912:
908:
904:
900:
872:
867:
831:
804:
777:
757:91.69 J/(K·mol)
753:
738:Thermochemistry
708:Refractive index
701:
699:
533:
521:
515:
509:
502:Chemical formula
442:
441:
426:
424:
398:
362:
351:
340:
321:Gmelin Reference
304:
296:
285:
274:
254:
234:
202:
178:
96:
63:
33:
29:
4436:
4435:
4431:
4430:
4429:
4427:
4426:
4425:
4391:
4390:
4389:
4384:
4374:
4372:
4362:
4360:
4350:
4348:
4328:
4154:
4130:
4121:
4074:
4064:
4007:
3995:
3976:Propionaldehyde
3951:Ethylene glycol
3940:
3932:
3928:
3899:
3897:
3890:
3846:Cyanohexatriyne
3832:
3825:
3772:
3765:
3700:
3693:
3653:
3606:
3599:
3570:Methoxy radical
3500:
3493:
3489:Thiocyanic acid
3370:
3363:
3273:
3213:Ethynyl radical
3149:
3143:
3142:
3141:
3140:
3134:
3133:
3132:
3131:
3122:
3113:Sulfur monoxide
3098:Sodium chloride
3083:Silicon carbide
2990:Diatomic carbon
2980:Carbon monoxide
2922:
2917:
2843:
2839:
2832:
2827:
2807:(12): 634–642,
2798:
2797:
2793:
2773:(2–3): 157–64,
2764:
2763:
2756:
2737:
2736:
2732:
2711:(23): 3470–73.
2701:
2700:
2696:
2685:
2678:
2677:
2670:
2652:
2651:
2638:
2630:
2628:
2624:
2618:
2603:
2593:
2592:
2583:
2561:
2560:
2556:
2539:
2538:
2534:
2527:
2517:
2516:
2512:
2505:
2482:
2481:
2477:
2446:
2445:
2441:
2435:
2431:
2416:
2403:
2402:
2398:
2392:
2379:
2378:
2369:
2359:
2346:
2345:
2341:
2333:
2318:
2308:
2307:
2300:
2286:
2276:
2265:
2264:
2260:
2242:
2241:
2237:
2209:
2208:
2204:
2187:
2181:
2179:
2175:
2164:
2162:"Archived copy"
2160:
2159:
2152:
2135:
2134:
2127:
2113:
2112:
2103:
2086:
2082:
2058:
2057:
2050:
2038:
2034:
2033:
2022:
2018:
1995:
1970:
1966:
1965:
1947:cytochrome P450
1908:
1804:
1788:
1713:
1708:
1684:
1672:carbon monoxide
1670:of mixtures of
1652:
1628:
1624:
1620:
1616:
1612:
1603:
1599:
1595:
1591:
1587:
1583:
1571:. For example,
1561:
1529:
1517:pharmaceuticals
1421:
1398:
1390:
1354:
1350:
1343:
1339:
1318:
1311:
1306:
1305:
1304: ?)
1295:
1291:
1287:
1283:
1255:
1248:
1189:Cyanogen iodide
1184:Thiocyanic acid
1172:
1157:
1144:
1131:
1108:
1102:
1092:
1090:
1088:
1086:
1082:
1076:
1067:
1049:
1043:
1013:
1010:
992:
991:
990:
989:
982:
975:
968:
964:
956:
925:
895:
881:
860:
832:
829:
823:
819:
816:
815:Std enthalpy of
805:
802:
796:
792:
789:
788:Std enthalpy of
778:
775:
768:
765:
754:
747:
730:
718:
716:
697:
695:
692:
668:
653:
636:
634:
625:
591:
531:
518:
512:
504:
490:
487:
482:
481:
470:
467:
466:
463:
457:
456:
445:
427:
420:
401:
381:
365:
352:
323:
314:
277:
257:
237:
214:
205:
192:
181:
168:
154:
153:
125:
124:
113:
112:
24:
17:
12:
11:
5:
4434:
4432:
4424:
4423:
4418:
4413:
4408:
4406:Alkanenitriles
4403:
4393:
4392:
4386:
4385:
4383:
4382:
4370:
4358:
4346:
4333:
4330:
4329:
4327:
4326:
4321:
4316:
4311:
4305:
4300:
4295:
4290:
4285:
4280:
4275:
4270:
4265:
4260:
4255:
4250:
4245:
4240:
4235:
4230:
4225:
4220:
4215:
4213:Cosmochemistry
4210:
4205:
4200:
4195:
4190:
4185:
4180:
4178:Astrochemistry
4175:
4170:
4164:
4162:
4156:
4155:
4153:
4152:
4147:
4142:
4137:
4132:
4128:
4124:
4119:
4115:
4110:
4105:
4100:
4095:
4090:
4084:
4082:
4076:
4075:
4073:
4072:
4067:
4062:
4058:
4053:
4048:
4043:
4038:
4033:
4031:Formyl radical
4028:
4023:
4017:
4011:
4009:
4001:
4000:
3997:
3996:
3994:
3993:
3988:
3983:
3978:
3973:
3968:
3963:
3961:Methyl acetate
3958:
3953:
3948:
3943:
3938:
3934:
3930:
3926:
3920:
3915:
3910:
3904:
3902:
3892:
3891:
3889:
3888:
3883:
3878:
3873:
3868:
3863:
3858:
3853:
3851:Dimethyl ether
3848:
3843:
3837:
3835:
3827:
3826:
3824:
3823:
3818:
3816:Methyl formate
3813:
3808:
3803:
3801:Glycolaldehyde
3798:
3793:
3788:
3783:
3777:
3775:
3767:
3766:
3764:
3763:
3758:
3753:
3748:
3743:
3738:
3736:Glycolonitrile
3733:
3731:Ethylene oxide
3728:
3723:
3722:
3721:
3711:
3705:
3703:
3695:
3694:
3692:
3691:
3686:
3681:
3676:
3671:
3666:
3661:
3656:
3651:
3647:
3642:
3637:
3632:
3630:Cyclopropenone
3627:
3622:
3617:
3611:
3609:
3601:
3600:
3598:
3597:
3592:
3587:
3582:
3577:
3572:
3567:
3562:
3557:
3552:
3547:
3542:
3537:
3532:
3530:Cyanoacetylene
3527:
3522:
3517:
3512:
3505:
3503:
3495:
3494:
3492:
3491:
3486:
3481:
3476:
3471:
3466:
3461:
3456:
3451:
3449:Methyl radical
3446:
3441:
3436:
3431:
3426:
3424:Isocyanic acid
3421:
3416:
3411:
3406:
3401:
3396:
3391:
3389:Isocyanic acid
3386:
3381:
3375:
3373:
3365:
3364:
3362:
3361:
3356:
3351:
3346:
3341:
3336:
3334:Sulfur dioxide
3331:
3326:
3321:
3316:
3311:
3309:Sodium cyanide
3306:
3301:
3296:
3291:
3286:
3281:
3276:
3271:
3267:
3262:
3257:
3252:
3247:
3242:
3237:
3232:
3226:
3220:
3218:Formyl radical
3215:
3210:
3205:
3200:
3195:
3190:
3185:
3180:
3178:Carbon dioxide
3175:
3170:
3165:
3159:
3157:
3151:
3150:
3125:
3123:
3121:
3120:
3115:
3110:
3105:
3100:
3095:
3090:
3085:
3080:
3075:
3070:
3065:
3059:
3054:
3049:
3043:
3038:
3033:
3028:
3026:Iron(II) oxide
3023:
3018:
3012:
3007:
3002:
2997:
2992:
2987:
2982:
2977:
2972:
2967:
2962:
2957:
2952:
2947:
2941:
2939:
2930:
2924:
2923:
2918:
2916:
2915:
2908:
2901:
2893:
2887:
2886:
2872:
2867:
2861:
2856:
2851:
2846:
2841:
2837:
2831:
2830:External links
2828:
2826:
2825:
2801:J. Occup. Med.
2791:
2767:Toxicol. Lett.
2754:
2730:
2694:
2668:
2636:
2616:
2581:
2554:
2532:
2510:
2504:978-3527306732
2503:
2475:
2439:
2429:
2414:
2396:
2390:
2367:
2339:
2298:
2289:|journal=
2258:
2249:Comptes rendus
2235:
2222:(2): 299–304.
2202:
2150:
2137:"Acetonitrile"
2125:
2101:
2080:
2048:
2019:
2017:
2014:
2013:
2012:
2006:alcohol groups
1994:
1991:
1939:glycolonitrile
1913:
1912:
1906:
1899:
1898:
1895:
1892:
1886:
1885:
1882:
1879:
1873:
1872:
1869:
1866:
1860:
1859:
1856:
1853:
1847:
1846:
1843:
1840:
1834:
1833:
1830:
1827:
1821:
1820:
1817:
1814:
1808:
1807:
1802:
1797:
1794:
1787:
1784:
1757:sodium nitrite
1712:
1709:
1707:
1704:
1683:
1680:
1651:
1648:
1606:
1605:
1560:
1557:
1528:
1525:
1420:
1417:
1329:methyl cyanide
1316:
1313:
1312:
1307:
1285:
1284:
1280:standard state
1277:
1274:
1273:
1267:
1266:
1262:
1261:
1256:
1253:
1250:
1249:
1247:
1246:
1241:
1236:
1231:
1226:
1221:
1216:
1214:Glycolonitrile
1211:
1206:
1201:
1196:
1191:
1186:
1181:
1175:
1173:
1170:
1167:
1166:
1162:
1161:
1158:
1152:
1149:
1148:
1145:
1139:
1136:
1135:
1132:
1126:
1123:
1122:
1113:
1112:
1109:
1100:
1098:
1095:
1094:
1083:
1074:
1072:
1069:
1068:
1066:
1065:
1059:
1052:
1050:
1041:
1039:
1036:
1035:
1028:
1027:
1024:
1018:
1017:
1014:
1007:
1004:
1003:
1000:
994:
993:
983:
976:
969:
954:
953:
952:
951:
949:
940:
939:
937:P305+P351+P338
926:
921:
918:
917:
896:
891:
888:
887:
882:
877:
874:
873:
861:
856:
853:
852:
842:
841:
837:
836:
833:
827:
821:
813:
810:
809:
806:
800:
794:
786:
783:
782:
779:
773:
762:
759:
758:
755:
743:
740:
739:
735:
734:
731:
726:
723:
722:
719:
714:
706:
703:
702:
700:10 cm/mol
693:
687:
684:
683:
680:
674:
673:
670:
666:
659:
658:
655:
651:
641:
640:
637:
632:
622:
619:
618:
615:
613:Vapor pressure
609:
608:
605:
596:
595:
592:
587:
584:
583:
580:
574:
573:
570:
564:
563:
560:
554:
553:
550:
544:
543:
540:
536:
535:
529:
523:
522:
516:
510:
505:
500:
497:
496:
492:
491:
489:
488:
485:
477:
476:
475:
472:
471:
469:
468:
464:
461:
460:
452:
451:
450:
447:
446:
444:
443:
430:
428:
416:
413:
412:
409:
403:
402:
400:
399:
391:
389:
383:
382:
380:
379:
375:
373:
367:
366:
364:
363:
355:
353:
345:
342:
341:
334:
328:
327:
324:
319:
316:
315:
313:
312:
308:
306:
298:
297:
287:
279:
278:
276:
275:
267:
265:
259:
258:
256:
255:
247:
245:
239:
238:
236:
235:
227:
225:
219:
218:
215:
210:
207:
206:
204:
203:
195:
193:
186:
183:
182:
180:
179:
171:
169:
164:
161:
160:
156:
155:
152:
151:
148:
145:
144:Methyl cyanide
142:
139:
136:
132:
131:
127:
126:
122:
121:
115:
114:
110:
109:
103:
102:
98:
97:
89:
88:
85:
84:
74:
59:
58:
55:
54:
44:
21:Acetyl cyanide
15:
13:
10:
9:
6:
4:
3:
2:
4433:
4422:
4419:
4417:
4414:
4412:
4409:
4407:
4404:
4402:
4399:
4398:
4396:
4381:
4371:
4369:
4359:
4357:
4347:
4345:
4344:
4335:
4334:
4331:
4325:
4322:
4320:
4317:
4315:
4312:
4309:
4306:
4304:
4301:
4299:
4296:
4294:
4291:
4289:
4286:
4284:
4281:
4279:
4276:
4274:
4271:
4269:
4266:
4264:
4261:
4259:
4256:
4254:
4251:
4249:
4246:
4244:
4243:Homochirality
4241:
4239:
4236:
4234:
4231:
4229:
4226:
4224:
4221:
4219:
4216:
4214:
4211:
4209:
4206:
4204:
4201:
4199:
4196:
4194:
4191:
4189:
4186:
4184:
4181:
4179:
4176:
4174:
4171:
4169:
4166:
4165:
4163:
4161:
4157:
4151:
4148:
4146:
4143:
4141:
4138:
4136:
4133:
4131:
4125:
4123:
4116:
4114:
4111:
4109:
4106:
4104:
4101:
4099:
4098:Methoxyethane
4096:
4094:
4091:
4089:
4086:
4085:
4083:
4081:
4077:
4071:
4068:
4066:
4059:
4057:
4054:
4052:
4049:
4047:
4044:
4042:
4039:
4037:
4034:
4032:
4029:
4027:
4024:
4021:
4018:
4016:
4013:
4012:
4010:
4006:
4002:
3992:
3989:
3987:
3984:
3982:
3981:Butyronitrile
3979:
3977:
3974:
3972:
3969:
3967:
3964:
3962:
3959:
3957:
3956:Ethyl formate
3954:
3952:
3949:
3947:
3944:
3942:
3935:
3924:
3921:
3919:
3916:
3914:
3911:
3909:
3906:
3905:
3903:
3901:
3893:
3887:
3884:
3882:
3881:Propionitrile
3879:
3877:
3874:
3872:
3869:
3867:
3864:
3862:
3859:
3857:
3854:
3852:
3849:
3847:
3844:
3842:
3839:
3838:
3836:
3834:
3828:
3822:
3819:
3817:
3814:
3812:
3809:
3807:
3804:
3802:
3799:
3797:
3794:
3792:
3789:
3787:
3784:
3782:
3779:
3778:
3776:
3774:
3768:
3762:
3761:Vinyl alcohol
3759:
3757:
3754:
3752:
3749:
3747:
3744:
3742:
3739:
3737:
3734:
3732:
3729:
3727:
3724:
3720:
3719:Vinyl cyanide
3717:
3716:
3715:
3714:Acrylonitrile
3712:
3710:
3707:
3706:
3704:
3702:
3696:
3690:
3687:
3685:
3682:
3680:
3679:Pentynylidyne
3677:
3675:
3672:
3670:
3667:
3665:
3662:
3660:
3657:
3655:
3648:
3646:
3643:
3641:
3638:
3636:
3633:
3631:
3628:
3626:
3623:
3621:
3618:
3616:
3613:
3612:
3610:
3608:
3602:
3596:
3593:
3591:
3588:
3586:
3583:
3581:
3578:
3576:
3575:Methylenimine
3573:
3571:
3568:
3566:
3563:
3561:
3558:
3556:
3553:
3551:
3548:
3546:
3543:
3541:
3538:
3536:
3533:
3531:
3528:
3526:
3523:
3521:
3518:
3516:
3513:
3510:
3507:
3506:
3504:
3502:
3496:
3490:
3487:
3485:
3482:
3480:
3477:
3475:
3472:
3470:
3467:
3465:
3462:
3460:
3457:
3455:
3454:Propynylidyne
3452:
3450:
3447:
3445:
3444:Methyl cation
3442:
3440:
3437:
3435:
3432:
3430:
3427:
3425:
3422:
3420:
3417:
3415:
3412:
3410:
3407:
3405:
3404:Fulminic acid
3402:
3400:
3397:
3395:
3392:
3390:
3387:
3385:
3382:
3380:
3377:
3376:
3374:
3372:
3366:
3360:
3357:
3355:
3352:
3350:
3347:
3345:
3342:
3340:
3337:
3335:
3332:
3330:
3327:
3325:
3322:
3320:
3317:
3315:
3312:
3310:
3307:
3305:
3302:
3300:
3297:
3295:
3292:
3290:
3287:
3285:
3282:
3280:
3279:Nitrous oxide
3277:
3275:
3268:
3266:
3263:
3261:
3258:
3256:
3253:
3251:
3248:
3246:
3243:
3241:
3238:
3236:
3233:
3230:
3227:
3224:
3221:
3219:
3216:
3214:
3211:
3209:
3206:
3204:
3201:
3199:
3196:
3194:
3191:
3189:
3186:
3184:
3181:
3179:
3176:
3174:
3173:Amino radical
3171:
3169:
3166:
3164:
3161:
3160:
3158:
3156:
3152:
3147:
3138:
3129:
3119:
3116:
3114:
3111:
3109:
3106:
3104:
3103:Sodium iodide
3101:
3099:
3096:
3094:
3091:
3089:
3086:
3084:
3081:
3079:
3076:
3074:
3071:
3069:
3066:
3063:
3060:
3058:
3055:
3053:
3050:
3047:
3044:
3042:
3039:
3037:
3034:
3032:
3029:
3027:
3024:
3022:
3019:
3016:
3013:
3011:
3008:
3006:
3003:
3001:
2998:
2996:
2993:
2991:
2988:
2986:
2985:Cyano radical
2983:
2981:
2978:
2976:
2973:
2971:
2968:
2966:
2965:Carbon cation
2963:
2961:
2958:
2956:
2953:
2951:
2948:
2946:
2943:
2942:
2940:
2938:
2934:
2931:
2929:
2925:
2921:
2914:
2909:
2907:
2902:
2900:
2895:
2894:
2891:
2884:
2880:
2876:
2873:
2871:
2868:
2865:
2862:
2860:
2857:
2855:
2852:
2850:
2847:
2845:
2834:
2833:
2829:
2822:
2818:
2814:
2810:
2806:
2802:
2795:
2792:
2788:
2784:
2780:
2776:
2772:
2768:
2761:
2759:
2755:
2750:
2746:
2745:
2740:
2734:
2731:
2726:
2722:
2718:
2714:
2710:
2707:
2706:
2698:
2695:
2691:
2684:
2683:
2675:
2673:
2669:
2665:
2661:
2660:
2655:
2649:
2647:
2645:
2643:
2641:
2637:
2627:on 2011-07-28
2623:
2619:
2617:2-7389-1278-8
2613:
2609:
2602:
2601:
2596:
2590:
2588:
2586:
2582:
2577:
2573:
2569:
2565:
2558:
2555:
2550:
2546:
2542:
2536:
2533:
2524:
2520:
2514:
2511:
2506:
2500:
2496:
2492:
2488:
2487:
2479:
2476:
2471:
2467:
2463:
2459:
2455:
2451:
2443:
2440:
2433:
2430:
2425:
2421:
2417:
2415:9783527302727
2411:
2407:
2400:
2397:
2393:
2391:0-12-745354-7
2387:
2383:
2376:
2374:
2372:
2368:
2362:
2356:
2355:
2350:
2343:
2340:
2336:on 2008-12-17
2332:
2328:
2324:
2317:
2316:
2311:
2305:
2303:
2299:
2294:
2281:
2273:
2269:
2262:
2259:
2254:
2250:
2246:
2239:
2236:
2230:
2225:
2221:
2217:
2213:
2206:
2203:
2198:
2192:
2178:on 2011-05-16
2174:
2170:
2163:
2157:
2155:
2151:
2146:
2142:
2138:
2132:
2130:
2126:
2121:
2117:
2110:
2108:
2106:
2102:
2097:
2091:
2083:
2077:
2073:
2069:
2065:
2062:. Cambridge:
2061:
2055:
2053:
2049:
2044:
2037:
2031:
2029:
2027:
2025:
2021:
2015:
2011:
2007:
2004:
2000:
1997:
1996:
1992:
1990:
1988:
1984:
1979:
1977:
1976:propionitrile
1961:
1959:
1955:
1951:
1950:monooxygenase
1948:
1944:
1940:
1936:
1932:
1928:
1924:
1920:
1909:
1900:
1891:
1888:
1887:
1878:
1875:
1874:
1865:
1864:Acrylonitrile
1862:
1861:
1852:
1851:Malononitrile
1849:
1848:
1839:
1838:Butyronitrile
1836:
1835:
1826:
1825:Propionitrile
1823:
1822:
1813:
1810:
1809:
1805:
1798:
1795:
1792:
1791:
1785:
1783:
1781:
1777:
1776:ethyl acetate
1773:
1769:
1764:
1762:
1758:
1754:
1750:
1746:
1742:
1738:
1734:
1730:
1724:
1722:
1718:
1710:
1705:
1703:
1701:
1700:acrylonitrile
1697:
1693:
1692:Hurricane Ike
1689:
1681:
1679:
1677:
1673:
1669:
1668:hydrogenation
1665:
1661:
1660:acrylonitrile
1657:
1656:acrylonitrile
1649:
1647:
1645:
1641:
1637:
1632:
1611:
1582:
1581:
1580:
1578:
1574:
1570:
1566:
1558:
1556:
1554:
1553:malononitrile
1550:
1546:
1542:
1538:
1534:
1526:
1524:
1522:
1518:
1513:
1511:
1507:
1502:
1500:
1496:
1492:
1488:
1483:
1481:
1477:
1473:
1468:
1466:
1462:
1458:
1455:of 3.92
1454:
1453:dipole moment
1450:
1446:
1442:
1437:
1434:
1430:
1426:
1418:
1416:
1414:
1409:
1407:
1404:of 1.16
1403:
1397:with a short
1396:
1388:
1384:
1380:
1376:
1375:acrylonitrile
1372:
1368:
1364:
1360:
1349:
1338:
1334:
1330:
1326:
1322:
1310:
1303:
1298:
1281:
1275:
1272:
1268:
1263:
1260:
1257:
1252:
1251:
1245:
1242:
1240:
1239:Pivalonitrile
1237:
1235:
1234:Malononitrile
1232:
1230:
1227:
1225:
1224:Propionitrile
1222:
1220:
1217:
1215:
1212:
1210:
1207:
1205:
1202:
1200:
1197:
1195:
1192:
1190:
1187:
1185:
1182:
1180:
1177:
1176:
1174:
1169:
1168:
1163:
1159:
1155:
1151:
1150:
1146:
1143:(Recommended)
1142:
1138:
1137:
1133:
1130:(Permissible)
1129:
1125:
1124:
1120:
1119:
1114:
1110:
1106:
1097:
1096:
1084:
1080:
1071:
1070:
1060:
1054:
1053:
1051:
1047:
1038:
1037:
1033:
1029:
1025:
1023:
1020:
1019:
1015:
1012:
1006:
1005:
1001:
999:
996:
995:
988:
981:
974:
950:
947:
946:
942:
941:
927:
924:
920:
919:
897:
894:
890:
889:
886:
883:
880:
876:
875:
871:
866:
862:
859:
855:
854:
850:
848:
843:
838:
834:
826:
818:
812:
811:
807:
799:
791:
785:
784:
780:
772:
767:
761:
760:
756:
751:
746:
745:Heat capacity
742:
741:
736:
732:
729:
728:Dipole moment
725:
724:
720:
713:
709:
705:
704:
694:
690:
686:
685:
681:
679:
676:
675:
671:
664:
661:
660:
656:
650:
646:
643:
642:
638:
631:
627:
621:
620:
616:
614:
611:
610:
606:
604:
603:
598:
597:
593:
590:
586:
585:
581:
579:
578:Boiling point
576:
575:
571:
569:
568:Melting point
566:
565:
561:
559:
556:
555:
551:
549:
546:
545:
541:
538:
537:
530:
528:
525:
524:
506:
503:
499:
498:
493:
484:
480:
473:
459:
455:
448:
440:
436:
435:DTXSID7020009
432:
431:
429:
419:
415:
414:
410:
408:
405:
404:
397:
393:
392:
390:
388:
385:
384:
377:
376:
374:
372:
369:
368:
361:
357:
356:
354:
348:
344:
343:
339:
335:
333:
330:
329:
325:
322:
318:
317:
310:
309:
307:
305:
300:
299:
295:
291:
288:
286:
284:ECHA InfoCard
281:
280:
273:
269:
268:
266:
264:
261:
260:
253:
249:
248:
246:
244:
241:
240:
233:
229:
228:
226:
224:
221:
220:
216:
213:
209:
208:
201:
197:
196:
194:
190:
185:
184:
177:
173:
172:
170:
167:
163:
162:
157:
149:
146:
143:
140:
138:Ethyl nitrile
137:
134:
133:
128:
123:Ethanenitrile
120:
116:
108:
104:
99:
95:
90:
79:
75:
69:
65:
64:
60:
49:
45:
39:
35:
34:
30:
27:Acetonitrile
22:
4336:
4319:Spectroscopy
4173:Astrobiology
4026:Formaldehyde
3918:Benzonitrile
3709:Acetaldehyde
3664:Methanethiol
3615:Acetonitrile
3614:
3520:Carbodiimide
3399:Formaldehyde
3394:Cyanoethynyl
3245:Iron cyanide
3240:Hydroperoxyl
3041:Nitric oxide
2804:
2800:
2794:
2770:
2766:
2748:
2742:
2733:
2708:
2703:
2697:
2681:
2658:
2629:, retrieved
2622:the original
2599:
2567:
2563:
2557:
2535:
2513:
2484:
2478:
2453:
2449:
2442:
2432:
2405:
2399:
2381:
2360:
2352:
2342:
2331:the original
2314:
2280:cite journal
2271:
2261:
2252:
2248:
2238:
2219:
2215:
2205:
2180:. Retrieved
2173:the original
2168:
2140:
2059:
2043:TedPella.com
2042:
1980:
1962:
1954:formaldehyde
1934:
1916:
1889:
1877:Acetonitrile
1876:
1765:
1725:
1714:
1685:
1653:
1633:
1607:
1562:
1530:
1514:
1503:
1484:
1476:electrolytes
1469:
1438:
1433:hydrocarbons
1431:filled with
1422:
1419:Applications
1410:
1393:skeleton is
1328:
1324:
1321:Acetonitrile
1320:
1319:
1117:
1031:
1009:Autoignition
944:
884:
846:
824:
797:
770:
749:
711:
672:195 nm
648:
629:
601:
371:RTECS number
338:acetonitrile
159:Identifiers
135:Cyanomethane
130:Other names
111:Acetonitrile
4293:Outer space
4203:Cosmic dust
4168:Abiogenesis
4080:Unconfirmed
4036:Heavy water
3876:Ethanethiol
3791:Cyanoallene
3781:Acetic acid
3751:Methylamine
3635:Diacetylene
3550:Formic acid
3540:Cyanomethyl
3198:Diazenylium
3188:CCP radical
3064:(molecular)
3048:(molecular)
3017:(molecular)
2541:Lowe, Derek
1983:thiocyanate
1974:that for a
1958:formic acid
1945:-dependent
1923:metabolised
1737:Convulsions
1719:to produce
1717:metabolised
1636:Lewis acids
1592:CN → PdCl
1063:(oral, rat)
1046:median dose
1032:Lethal dose
1011:temperature
998:Flash point
879:Signal word
624:Henry's law
539:Appearance
495:Properties
290:100.000.760
252:ChEMBL45211
232:CHEBI:38472
4395:Categories
4208:Cosmic ray
4150:Silylidyne
4113:Hemolithin
4088:Anthracene
4005:Deuterated
3986:Pyrimidine
3796:Ethanimine
3659:Ketenimine
3515:Butadiynyl
3339:Thioformyl
3193:Chloronium
2883:our galaxy
2662:, Geneva:
2631:2008-08-19
2570:(47): 27.
2519:US 4179462
2255:: 383–384.
2182:2011-03-31
2016:References
1927:microsomes
1729:pulse rate
1650:Production
1644:superacids
1613:[Cu(CH
1441:non-protic
1331:), is the
1061:2.46 g/kg
1026:4.4–16.0%
858:Pictograms
817:combustion
678:Absorbance
527:Molar mass
396:Z072SB282N
263:ChemSpider
187:3D model (
166:CAS Number
4140:Phosphine
4008:molecules
3941:fullerene
3841:Acetamide
3645:Formamide
3525:Cyanamide
3379:Acetylene
3354:Tricarbon
3265:Methylene
3250:Isoformyl
3155:Triatomic
2928:Molecules
2879:Sgr B2(M)
2606:, Paris:
2090:cite book
1987:rhodanese
1793:Compound
1664:acetamide
1491:viscosity
1487:UV cutoff
1425:butadiene
1387:butadiene
1348:structure
1335:with the
849:labelling
790:formation
764:Std molar
594:Miscible
407:UN number
378:AL7700000
311:200-835-2
303:EC Number
4411:Solvents
4127:Linear C
4108:Graphene
4020:Ammonium
3821:Acrolein
3684:Propynal
3669:Methanol
3640:Ethylene
3509:Ammonium
3284:Nitroxyl
3108:Sulfanyl
3052:Imidogen
3046:Nitrogen
3015:Hydrogen
2960:Argonium
2937:Diatomic
2821:14434606
2656:(1993),
2597:(2004),
2543:(2009).
2470:27116374
2424:51068223
2312:(2002),
2191:cite web
2147:(NIOSH).
2122:(NIOSH).
1993:See also
1919:nitriles
1806:(mg/kg)
1711:Toxicity
1688:Olympics
1551:affords
1541:thiamine
1501:(HPLC).
1493:and low
1445:miscible
1402:distance
1219:Cyanogen
1160:500 ppm
945:NFPA 704
840:Hazards
691:(χ)
626:constant
4416:Ligands
4273:Kerogen
4160:Related
4103:Glycine
4056:Propyne
4015:Ammonia
3913:Benzene
3908:Acetone
3900:or more
3871:Propene
3856:Ethanol
3746:Propyne
3565:Methane
3434:Ketenyl
3384:Ammonia
2787:6287676
2725:3062198
2116:"#0006"
2003:protect
1969:⁄
1772:Acetone
1751:, with
1676:ammonia
1472:battery
1371:organic
1367:cyanide
1359:nitrile
1337:formula
1302:what is
1300: (
1055:2 g/kg
766:entropy
733:3.92 D
645:Acidity
628: (
607:−0.334
558:Density
347:PubChem
217:741857
176:75-05-8
4324:Tholin
4145:Pyrene
3590:Silane
3560:Ketene
3062:Oxygen
2819:
2785:
2723:
2614:
2528:
2501:
2468:
2422:
2412:
2388:
2274:: 291.
2078:
1941:by an
1935:et al.
1759:, and
1753:oxygen
1733:nausea
1706:Safety
1666:or by
1623:. The
1588:+ 2 CH
1569:ligand
1543:, and
1489:, low
1395:linear
1389:. The
1297:verify
1294:
885:Danger
721:1.344
682:≤0.10
663:UV-vis
532:41.053
479:SMILES
243:ChEMBL
101:Names
4310:(PAH)
3898:atoms
3833:atoms
3773:atoms
3771:Eight
3701:atoms
3699:Seven
3607:atoms
3501:atoms
3371:atoms
3359:Water
3289:Ozone
3231:(HNC)
3225:(HCN)
2686:(PDF)
2625:(PDF)
2604:(PDF)
2334:(PDF)
2319:(PDF)
2176:(PDF)
2165:(PDF)
2039:(PDF)
1985:(the
1943:NADPH
1897:3000
1884:2460
1799:Oral
1642:. In
1638:like
1508:from
1465:LC–MS
1391:N≡C−C
1355:C−C≡N
1259:DBNPA
1118:NIOSH
696:−28.0
454:InChI
411:1648
223:ChEBI
189:JSmol
3831:Nine
3499:Five
3409:HCCN
3369:Four
3329:SiNC
2817:PMID
2783:PMID
2721:PMID
2612:ISBN
2608:INRS
2499:ISBN
2466:PMID
2420:OCLC
2410:ISBN
2386:ISBN
2293:help
2197:link
2096:link
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1774:and
1741:coma
1739:and
1674:and
1584:PdCl
1519:and
1463:and
1461:HPLC
1346:and
1325:MeCN
1154:IDLH
933:P280
929:P210
915:H332
911:H319
907:H312
903:H302
899:H225
600:log
548:Odor
486:CC#N
387:UNII
360:6342
332:MeSH
326:895
272:6102
147:MeCN
4122:NCO
4022:ion
3929:, C
3896:Ten
3605:Six
3511:ion
2809:doi
2775:doi
2749:L65
2713:doi
2709:260
2572:doi
2491:doi
2458:doi
2224:doi
2068:doi
1925:in
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1845:50
1832:40
1819:10
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1600:CN)
1596:(CH
1399:C≡N
1381:in
1141:REL
1128:PEL
847:GHS
828:298
801:298
774:298
667:max
657:25
423:EPA
350:CID
150:ACN
4397::
3939:70
3931:60
3927:60
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2781:,
2771:12
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1894:—
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1073:LC
1042:50
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931:,
913:,
909:,
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901:,
851::
820:(Δ
793:(Δ
669:)
665:(λ
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647:(p
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4065:D
4063:2
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3270:N
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715:D
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520:N
517:3
514:H
511:2
508:C
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