447:
274:
1445:
1340:
54:
708:
713:
70:
703:
44:
1248:
985:
1386:
2191:
Moussa, Jamal; Guyard-Duhayon, Carine; Herson, Patrick; Amouri, Hani; Rager, Marie Noelle; Jutand, Anny (2004). "η-Semiquinone
Complexes and the Related η4-Benzoquinone of (Pentamethylcyclopentadienyl)rhodium and -iridium: Synthesis, Structures, Hydrogen Bonding, and Electrochemical Behavior".
1435:
or mixtures containing benzene and benzene compounds, such as petrol. The compound can interfere with cellular respiration, and kidney damage has been found in animals receiving severe exposure. It is excreted in its original form and also as variations of its own metabolite, hydroquinone.
1892:
Lü, Jian-Ming; Rosokha, Sergiy V; Neretin, Ivan S; Kochi, Jay K (2006). "Quinones as
Electron Acceptors. X-Ray Structures, Spectral (EPR, UV−vis) Characteristics and Electron-Transfer Reactivities of Their Reduced Anion Radicals as Separated vs Contact Ion Pairs".
1371:, wherein a palladium salt catalyzes the conversion of an alkene to a ketone. This reaction is typically carried out using pressurized oxygen as the oxidizer, but benzoquinone can sometimes preferred. It is also used as a reagent in some variants on
1468:
has found insufficient evidence to comment on the compound's carcinogenicity, but has noted that it can easily pass into the bloodstream and that it showed activity in depressing bone marrow production in mice and can inhibit
1464:. It is particularly irritating to the eyes and respiratory system. Its ability to sublime at commonly encountered temperatures allows for a greater airborne exposure risk than might be expected for a room-temperature solid.
721:
683:
1840:
811:
1611:
1589:
908:
998:
2291:
Lin, Y. S.; McKelvey, W.; Waidyanatha, S.; Rappaport, S. M. (2006). "Variability of
Albumin Adducts of 1,4-Benzoquinone, a Toxic Metabolite of Benzene, in Human Volunteers".
1231:, even at atmospheric pressure, allowing for an effective purification. Impure samples are often dark-colored due to the presence of quinhydrone, a dark green 1:1
2128:
1283:
and rubber manufacture as a reducing agent and antioxidant. Benzoquinonium is a skeletal muscle relaxant, ganglion blocking agent that is made from benzoquinone.
1339:
496:
1465:
1271:}, which adopts a more delocalized structure. Further reduction coupled to protonation gives the hydroquinone, wherein the C6 ring is fully delocalized.
1404:
807:
1068:
2106:
1980:
1714:
1681:
1557:
1071:. 1,4-Benzoquinone is sensitive toward both strong mineral acids and alkali, which cause condensation and decomposition of the compound.
1928:
Cavallito, Chester J.; Soria, Albert E.; Hoppe, James O. (1950). "Amino- and
Ammonium-alkylaminobenzoquinones as Curarimimetic Agents".
2060:
461:
2157:"Stereoselective Total Synthesis and Enantioselective Formal Synthesis of the Antineoplastic Sesquiterpene Quinone Metachromin A"
1494:
1259:
Benzoquinone is a planar molecule with localized, alternating C=C, C=O, and C–C bonds. Reduction gives the semiquinone anion C
154:
1228:
664:
322:
1360:
solution reduces a solution of benzoquinone to hydroquinone, which can be reoxidized back to the quinone with a solution of
1067:; an oxidant, forming the dihydroxy derivative; and an alkene, undergoing addition reactions, especially those typical for
795:
1005:
799:
769:
394:
712:
425:
847:
707:
53:
2340:
1541:
932:
919:
1423:
is another potent oxidant and dehydrogenation agent. Monochloro-p-benzoquinone is yet another but milder oxidant.
2345:
1327:
281:
1489:
161:
1854:
Sakurai, T. (1968). "On the refinement of the crystal structures of phenoquinone and monoclinic quinhydrone".
835:
1047:. In a pure state, it forms bright-yellow crystals with a characteristic irritating odor, resembling that of
831:
1232:
819:
646:
269:
1368:
735:
702:
695:
231:
1835:
1863:
1055:, and hot plastic or formaldehyde. This six-membered ring compound is the oxidized derivative of 1,4-
82:
43:
1538:
Nomenclature of
Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)
1084:
783:
442:
120:
1444:
1367:
Due to its ability to function as an oxidizer, 1,4-benzoquinone can be found in methods using the
1251:
C–C and C–O bond distances in benzoquinone (Q), its 1e reduced derivative (Q), and hydroquinone (H
2316:
1782:
Re-evaluation of Some
Organic Chemicals, Hydrazine and Hydrogen Peroxide (Part 1, Part 2, Part 3)
1431:
1,4-Benzoquinone is a toxic metabolite found in human blood and can be used to track exposure to
1331:
1088:
775:
191:
630:
Slightly soluble in petroleum ether; soluble in acetone; 10% in ethanol, benzene, diethyl ether
179:
1780:
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967:
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524:
1201:. This method is mainly practiced in PRC where environmental regulations are more relaxed.
823:
403:
69:
2350:
1296:
803:
300:
251:
2089:
McOmie, J. F. W.; Blatchly, J. M. (2011). "The Thiele-Winter
Acetoxylation of Quinones".
815:
130:
1867:
446:
273:
211:
1514:
1361:
1334:
in 1900. An application is found in this step of the total synthesis of
Metachromin A:
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635:
2334:
1315:
1311:
1217:
1140:
603:
593:
262:
2320:
2176:
2156:
1330:, who first described it in 1898, and after Ernst Winter, who further described its
855:
1236:
1080:
1056:
779:
2124:"Ueber die Einwirkung von Essigsäure-anhydrid auf Chinon und auf Dibenzoylstyrol"
791:
367:
2098:
1549:
1509:
1300:
1280:
886:
862:
757:
17:
1996:
Oda, M.; Kawase, T.; Okada, T.; Enomoto, T. (1996). "2-Cyclohexene-1,4-dione".
1247:
839:
2304:
2141:
1875:
1585:
625:
552:
312:
242:
2270:
2234:
2045:
2011:
1972:
1949:
1814:
1761:
1738:
1643:
1603:
1407:(DDQ) is a stronger oxidant and dehydrogenation agent than 1,4-benzoquinone.
749:
1477:
1408:
414:
2312:
1963:
Yang, T.-K.; Shen, C.-Y. (2004). "1,4-Benzoquinone". In L. Paquette (ed.).
1914:
1343:
An application of the Thiele reaction, involving a benzoquinone derivative.
1190:
are produced. Subsequent oxidation of the hydroquinone gives the quinone.
1083:, which can be obtained by several routes. One route involves oxidation of
1706:
1673:
761:
1504:
1470:
1461:
1457:
1399:
1379:
1209:
1187:
1048:
1941:
1279:
Quinone is mainly used as a precursor to hydroquinone, which is used in
1432:
1194:
583:
354:
282:
2205:
1906:
745:
1473:
1213:
1147:
1064:
1060:
1052:
222:
2123:
975:
Except where otherwise noted, data are given for materials in their
1349:
Benzoquinone is also used to suppress double-bond migration during
342:
1443:
1385:
1384:
1246:
1204:
Oxidation of hydroquinone is facile. One such method makes use of
741:
378:
202:
160:
153:
143:
1216:
or an iodine salt as a catalyst for the oxidation occurring in a
843:
945:
851:
753:
573:
333:
2219:
Vogel, E.; Klug, W.; Breuer, A. (1974). "1,6-Methanoannulene".
1059:. The molecule is multifunctional: it exhibits properties of a
1608:
Immediately
Dangerous to Life or Health Concentrations (IDLH)
1193:
Quinone was originally prepared industrially by oxidation of
1338:
827:
430:
52:
42:
1146:
Another major process involves the direct hydroxylation of
1460:(redness, rashes on skin) and lead on to localized tissue
1079:
1,4-Benzoquinone is prepared industrially by oxidation of
1456:
1,4-Benzoquinone is able to stain skin dark brown, cause
2061:"Process for production of 2,4,5-trihydroxyacetophenone"
1227:
When heated to near its melting point, 1,4-benzoquinone
867:
38 to 93 °C; 100 to 200 °F; 311 to 366 K
1756:, 2002, Wiley-VCH, Weinheim. 2005 Wiley-VCH, Weinheim.
993:
1628:
Underwood, H. W. Jr.; Walsh, W. L. (1936). "Quinone".
1838:, "Process for the preparation of p-benzoquinone"
1612:
National
Institute for Occupational Safety and Health
1590:
National Institute for Occupational Safety and Health
1091:. The net reaction can be represented as follows:
321:
1291:It is used as a hydrogen acceptor and oxidant in
1143:) and the hydroquinone. Acetone is a coproduct.
178:
2032:Vliet, E. B. (1941). "Hydroquinone Triacetate".
366:
2255:Harman, R. E. (1955). "Chloro-p-benzoquinone".
1729:Gerhard Franz, Roger A. Sheldon "Oxidation" in
129:
2129:Berichte der Deutschen Chemischen Gesellschaft
1965:Encyclopedia of Reagents for Organic Synthesis
1754:Ullmann's Encyclopedia of Industrial Chemistry
1731:Ullmann's Encyclopedia of Industrial Chemistry
1378:1,4-Benzoquinone is used in the synthesis of
8:
1299:reagent. It is also used as a dienophile in
1532:
1530:
2155:Almeida, W. P.; Correia, C. R. D. (1999).
1697:Patai, Saul; Rappoport, Zvi, eds. (1988).
1664:Patai, Saul; Rappoport, Zvi, eds. (1988).
1623:
1621:
1452:sprays 1,4-Benzoquinone to deter predators
445:
272:
250:
31:
2175:
2164:Journal of the Brazilian Chemical Society
1748:
1746:
1405:2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
402:
1930:Journal of the American Chemical Society
1895:Journal of the American Chemical Society
1887:
1885:
1584:NIOSH Pocket Guide to Chemical Hazards.
470:InChI=1S/C6H4O2/c7-5-1-2-6(8)4-3-5/h1-4H
1526:
501:
480:InChI=1/C6H4O2/c7-5-1-2-6(8)4-3-5/h1-4H
466:
441:
1774:
1772:
1770:
1699:The Quinonoid Compounds: Vol. 2 (1988)
1666:The Quinonoid Compounds: Vol. 1 (1988)
1579:
1577:
1575:
1573:
1571:
1569:
598:115 °C (239 °F; 388 K)
263:
1752:Phillip M. Hudnall "Hydroquinone" in
473:Key: AZQWKYJCGOJGHM-UHFFFAOYSA-N
230:
210:
7:
1779:"1,4-Benzoquinone (para-Quinone)".
483:Key: AZQWKYJCGOJGHM-UHFFFAOYAR
357:
341:
2093:. Vol. 19. pp. 199–277.
1139:The reaction proceeds via the bis(
25:
1967:. New York: J. Wiley & Sons.
1389:Structure of Cp*Rh(para-quinone).
1856:Acta Crystallographica Section B
1799:Vliet, E. B. (1922). "Quinone".
1495:Benzoquinonetetracarboxylic acid
983:
895:93.8 mg/kg (mouse, subcutaneous)
893:296 mg/kg (mammal, subcutaneous)
711:
706:
701:
536:
68:
2177:10.1590/S0103-50531999000500011
1295:. 1,4-Benzoquinone serves as a
979:(at 25 °C , 100 kPa).
1542:The Royal Society of Chemistry
1318:. This reaction is called the
665:Occupational safety and health
542:
530:
1:
913:(US health exposure limits):
87:Cyclohexa-2,5-diene-1,4-dione
1733:, Wiley-VCH, Weinheim, 2000
2099:10.1002/0471264180.or019.03
1550:10.1039/9781849733069-FP001
875:or concentration (LD, LC):
640:0.1 mmHg (25 °C)
38:
2367:
2279:, vol. 4, p. 148
2243:, vol. 6, p. 731
2020:, vol. 9, p. 186
1823:, vol. 1, p. 482
1652:, vol. 2, p. 553
1544:. 2014. pp. 723–724.
1397:
1314:to give the triacetate of
1275:Reactions and applications
2305:10.1080/13547500500382975
2142:10.1002/cber.189803101226
1876:10.1107/S0567740868002451
1394:Related 1,4-benzoquinones
1306:Benzoquinone reacts with
973:
956:
907:
871:
682:
662:
657:
620:11 g/L (18 °C)
588:1.318 g/cm at 20 °C
517:
492:
457:
113:
93:
81:
76:
67:
37:
2271:10.15227/orgsyn.035.0022
2235:10.15227/orgsyn.054.0011
2046:10.15227/orgsyn.004.0035
2012:10.15227/orgsyn.073.0253
1973:10.1002/047084289X.rb033
1815:10.15227/orgsyn.016.0073
1762:10.1002/14356007.a13_499
1739:10.1002/14356007.a18_261
1644:10.15227/orgsyn.002.0085
1490:Tetrahydroxybenzoquinone
1186:O Both hydroquinone and
770:Precautionary statements
2059:Knowles, M. B. (1952).
1233:charge-transfer complex
1069:α,β-unsaturated ketones
939:TWA 0.4 mg/m (0.1 ppm)
926:TWA 0.4 mg/m (0.1 ppm)
647:Magnetic susceptibility
1453:
1390:
1369:Wacker-Tsuji oxidation
1344:
1324:Thiele–Winter reaction
1256:
58:
48:
1836:US patent 4973720
1707:10.1002/9780470772126
1674:10.1002/9780470772119
1476:involved in cellular
1447:
1398:Further information:
1388:
1382:and related analogs.
1342:
1250:
1063:, being able to form
901:130 mg/kg (rat, oral)
897:8.5 mg/kg (mouse, IP)
653:−38.4·10 cm/mol
578:Acrid, chlorine-like
504:O=C\1\C=C/C(=O)/C=C/1
56:
46:
1020:, commonly known as
83:Preferred IUPAC name
2122:Thiele, J. (1898).
1942:10.1021/ja01162a088
1868:1968AcCrB..24..403S
1243:Structure and redox
903:25 mg/kg (rat, IV)
615:Solubility in water
560: g·mol
192:Beilstein Reference
57:Space-filling model
34:
2070:. Eastman Kodak Co
1788:. IARC Monographs.
1454:
1391:
1345:
1332:reaction mechanism
1257:
1089:Hock rearrangement
1085:diisopropylbenzene
1006:Infobox references
957:Related compounds
948:(Immediate danger)
59:
49:
32:
2341:1,4-Benzoquinones
2277:Collected Volumes
2258:Organic Syntheses
2241:Collected Volumes
2222:Organic Syntheses
2206:10.1021/om049292t
2200:(26): 6231–6238.
2108:978-0-471-19619-8
2091:Organic Reactions
2034:Organic Syntheses
2018:Collected Volumes
1999:Organic Syntheses
1982:978-0-471-93623-7
1907:10.1021/ja066471o
1821:Collected Volumes
1802:Organic Syntheses
1716:978-0-470-77212-6
1683:978-0-470-77211-9
1650:Collected Volumes
1631:Organic Syntheses
1559:978-0-85404-182-4
1450:bombardier beetle
1373:Wacker oxidations
1351:olefin metathesis
1293:organic synthesis
1287:Organic synthesis
1222:isopropyl alcohol
1206:hydrogen peroxide
1199:manganese dioxide
1197:, for example by
1152:hydrogen peroxide
1029:chemical compound
1014:Chemical compound
1012:
1011:
963:Related compounds
736:Hazard statements
426:CompTox Dashboard
162:Interactive image
155:Interactive image
63:
62:
33:1,4-Benzoquinone
27:Chemical compound
16:(Redirected from
2358:
2346:Oxidizing agents
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2288:
2282:
2280:
2273:
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2244:
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2216:
2210:
2209:
2188:
2182:
2181:
2179:
2161:
2152:
2146:
2145:
2136:(1): 1247–1249.
2119:
2113:
2112:
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2075:
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1953:
1936:(6): 2661–2665.
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1593:
1581:
1564:
1563:
1534:
1500:1,2-Benzoquinone
1358:potassium iodide
1308:acetic anhydride
1235:of quinone with
1018:1,4-Benzoquinone
996:
990:
987:
986:
968:1,2-Benzoquinone
857:
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532:
525:Chemical formula
509:C1=CC(=O)C=CC1=O
450:
449:
434:
432:
406:
370:
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345:
325:
301:Gmelin Reference
284:
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133:
96:1,4-Benzoquinone
72:
47:Skeletal formula
39:
35:
21:
18:1,4-benzoquinone
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1402:
1396:
1328:Johannes Thiele
1320:Thiele reaction
1297:dehydrogenation
1289:
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1001: ?)
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988:
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900:
899:5.6 mg/kg (rat)
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2068:Google Patents
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1517:
1515:Ardisiaquinone
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1492:
1485:
1482:
1441:
1438:
1428:
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1420:
1416:
1412:
1395:
1392:
1362:silver nitrate
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982:
981:
977:standard state
974:
971:
970:
965:
962:
959:
958:
954:
953:
950:
944:
941:
940:
937:
931:
928:
927:
924:
918:
915:
914:
905:
904:
891:
882:
880:
877:
876:
869:
868:
865:
859:
858:
812:P305+P351+P338
773:
768:
765:
764:
739:
734:
731:
730:
725:
720:
717:
716:
699:
694:
691:
690:
680:
679:
676:
673:
670:
669:
660:
659:
655:
654:
651:
645:
642:
641:
638:
636:Vapor pressure
632:
631:
628:
622:
621:
618:
613:
610:
609:
606:
600:
599:
596:
590:
589:
586:
580:
579:
576:
570:
569:
566:
562:
561:
555:
549:
548:
545:
539:
533:
528:
523:
520:
519:
515:
514:
512:
511:
508:
506:
503:
495:
494:
493:
490:
489:
487:
486:
482:
479:
478:
476:
472:
469:
468:
460:
459:
458:
455:
454:
452:
451:
438:
436:
424:
421:
420:
417:
411:
410:
408:
407:
399:
397:
391:
390:
388:
387:
383:
381:
375:
374:
372:
371:
363:
361:
353:
350:
349:
347:
346:
338:
336:
330:
329:
327:
326:
318:
316:
311:
308:
307:
304:
299:
296:
295:
293:
292:
288:
286:
278:
277:
267:
259:
258:
256:
255:
247:
245:
239:
238:
236:
235:
227:
225:
219:
218:
216:
215:
207:
205:
199:
198:
195:
190:
187:
186:
184:
183:
175:
173:
169:
168:
166:
165:
158:
150:
148:
141:
138:
137:
135:
134:
126:
124:
119:
116:
115:
111:
110:
95:
91:
90:
86:
85:
79:
78:
74:
73:
65:
64:
61:
60:
50:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
2363:
2352:
2349:
2347:
2344:
2342:
2339:
2338:
2336:
2322:
2318:
2314:
2310:
2306:
2302:
2298:
2294:
2287:
2284:
2278:
2272:
2268:
2264:
2260:
2259:
2251:
2248:
2242:
2236:
2232:
2228:
2224:
2223:
2215:
2212:
2207:
2203:
2199:
2195:
2187:
2184:
2178:
2173:
2169:
2165:
2158:
2151:
2148:
2143:
2139:
2135:
2131:
2130:
2125:
2118:
2115:
2110:
2104:
2100:
2096:
2092:
2085:
2082:
2069:
2062:
2055:
2052:
2047:
2043:
2039:
2035:
2028:
2025:
2019:
2013:
2009:
2005:
2001:
2000:
1992:
1989:
1984:
1978:
1974:
1970:
1966:
1959:
1956:
1951:
1947:
1943:
1939:
1935:
1931:
1924:
1921:
1916:
1912:
1908:
1904:
1900:
1896:
1888:
1886:
1882:
1877:
1873:
1869:
1865:
1861:
1857:
1850:
1847:
1837:
1831:
1828:
1822:
1816:
1812:
1808:
1804:
1803:
1795:
1792:
1784:
1783:
1775:
1773:
1771:
1767:
1763:
1759:
1755:
1749:
1747:
1743:
1740:
1736:
1732:
1726:
1723:
1718:
1712:
1708:
1704:
1700:
1693:
1690:
1685:
1679:
1675:
1671:
1667:
1660:
1657:
1651:
1645:
1641:
1637:
1633:
1632:
1624:
1622:
1618:
1613:
1609:
1605:
1599:
1596:
1591:
1587:
1580:
1578:
1576:
1574:
1572:
1570:
1566:
1561:
1555:
1551:
1547:
1543:
1540:. Cambridge:
1539:
1533:
1531:
1527:
1520:
1516:
1513:
1511:
1508:
1506:
1503:
1501:
1498:
1496:
1493:
1491:
1488:
1487:
1483:
1481:
1479:
1475:
1472:
1467:
1463:
1459:
1451:
1446:
1439:
1437:
1434:
1426:
1424:
1410:
1406:
1401:
1393:
1387:
1383:
1381:
1376:
1374:
1370:
1365:
1363:
1359:
1354:
1352:
1341:
1337:
1336:
1335:
1333:
1329:
1325:
1321:
1317:
1316:hydroxyquinol
1313:
1312:sulfuric acid
1309:
1304:
1302:
1298:
1294:
1286:
1284:
1282:
1274:
1272:
1249:
1242:
1240:
1238:
1234:
1230:
1225:
1223:
1219:
1218:polar solvent
1215:
1211:
1207:
1202:
1200:
1196:
1191:
1189:
1153:
1149:
1144:
1142:
1141:hydroperoxide
1094:
1093:
1092:
1090:
1086:
1082:
1074:
1072:
1070:
1066:
1062:
1058:
1054:
1050:
1034:
1030:
1026:
1024:
1019:
1007:
1000:
995:
978:
972:
969:
966:
961:
960:
955:
951:
947:
943:
942:
938:
935:(Recommended)
934:
930:
929:
925:
922:(Permissible)
921:
917:
916:
912:
911:
906:
892:
888:
879:
878:
874:
870:
866:
864:
861:
860:
774:
771:
767:
766:
740:
737:
733:
732:
729:
726:
723:
719:
718:
714:
709:
704:
700:
697:
693:
692:
688:
686:
681:
677:
672:
671:
667:
666:
661:
656:
652:
648:
644:
643:
639:
637:
634:
633:
629:
627:
624:
623:
619:
616:
612:
611:
607:
605:
604:Boiling point
602:
601:
597:
595:
594:Melting point
592:
591:
587:
585:
582:
581:
577:
575:
572:
571:
568:Yellow solid
567:
564:
563:
556:
554:
551:
550:
529:
526:
522:
521:
516:
507:
502:
498:
491:
477:
467:
463:
456:
448:
444:
443:DTXSID6020145
440:
439:
437:
427:
423:
422:
418:
416:
413:
412:
405:
401:
400:
398:
396:
393:
392:
385:
384:
382:
380:
377:
376:
369:
365:
364:
362:
356:
352:
351:
344:
340:
339:
337:
335:
332:
331:
324:
320:
319:
317:
314:
310:
309:
305:
302:
298:
297:
290:
289:
287:
285:
280:
279:
275:
271:
268:
266:
264:ECHA InfoCard
261:
260:
253:
249:
248:
246:
244:
241:
240:
233:
229:
228:
226:
224:
221:
220:
213:
209:
208:
206:
204:
201:
200:
196:
193:
189:
188:
181:
177:
176:
174:
171:
170:
163:
159:
156:
152:
151:
149:
145:
140:
139:
132:
128:
127:
125:
122:
118:
117:
112:
107:
103:-Benzoquinone
102:
92:
84:
80:
75:
71:
66:
55:
51:
45:
41:
40:
36:
30:
19:
2299:(1): 14–27.
2296:
2292:
2286:
2276:
2262:
2256:
2250:
2240:
2226:
2220:
2214:
2197:
2193:
2186:
2167:
2163:
2150:
2133:
2127:
2117:
2090:
2084:
2072:. Retrieved
2067:
2054:
2037:
2033:
2027:
2017:
2003:
1997:
1991:
1964:
1958:
1933:
1929:
1923:
1898:
1894:
1859:
1855:
1849:
1830:
1820:
1806:
1800:
1794:
1781:
1753:
1730:
1725:
1698:
1692:
1665:
1659:
1649:
1635:
1629:
1607:
1598:
1537:
1455:
1430:
1403:
1377:
1366:
1355:
1348:
1323:
1319:
1305:
1290:
1278:
1258:
1237:hydroquinone
1226:
1203:
1192:
1145:
1138:
1081:hydroquinone
1078:
1057:hydroquinone
1022:
1021:
1017:
1016:
909:
872:
727:
684:
674:Main hazards
663:
379:RTECS number
114:Identifiers
105:
100:
98:Benzoquinone
94:Other names
29:
2074:24 December
1510:Duroquinone
1353:reactions.
1303:reactions.
1301:Diels Alder
1281:photography
1075:Preparation
887:median dose
873:Lethal dose
863:Flash point
722:Signal word
668:(OHS/OSH):
565:Appearance
518:Properties
270:100.003.097
212:CHEBI:16509
2335:Categories
2293:Biomarkers
1521:References
1427:Metabolism
1356:An acidic
1150:by acidic
696:Pictograms
626:Solubility
553:Molar mass
404:3T006GV98U
313:IUPHAR/BPS
243:ChemSpider
232:ChEMBL8320
142:3D model (
121:CAS Number
1950:0002-7863
1604:"Quinone"
1478:apoptosis
1409:Chloranil
1127:+ 2 OCMe
1031:with the
952:100 mg/m
848:P403+P233
836:P337+P313
832:P332+P313
808:P304+P340
804:P302+P352
800:P301+P310
687:labelling
608:Sublimes
415:UN number
386:DK2625000
291:203-405-2
283:EC Number
2321:13198966
2313:16484134
1915:17177421
1614:(NIOSH).
1592:(NIOSH).
1505:Quinones
1484:See also
1471:protease
1462:necrosis
1458:erythema
1400:quinones
1380:Bromadol
1229:sublimes
1210:oxidizer
1188:catechol
1162:OH + H
1087:and the
1049:chlorine
1025:-quinone
658:Hazards
649:(χ)
131:106-51-4
108:-Quinone
2040:: 317.
2006:: 253.
1864:Bibcode
1586:"#0542"
1474:enzymes
1433:benzene
1220:; e.g.
1208:as the
1195:aniline
1033:formula
1027:, is a
999:what is
997: (
584:Density
558:108.096
355:PubChem
197:773967
2351:Enones
2319:
2311:
2265:: 22.
2229:: 11.
2105:
1979:
1948:
1913:
1842:
1809:: 85.
1713:
1680:
1638:: 73.
1556:
1440:Safety
1326:after
1214:iodine
1148:phenol
1111:+ 3 O
1065:oximes
1061:ketone
1053:bleach
994:verify
991:
728:Danger
678:Toxic
497:SMILES
343:C00472
223:ChEMBL
180:B01254
172:3DMet
77:Names
2317:S2CID
2160:(PDF)
2064:(PDF)
1786:(PDF)
1411:1,4-C
1170:→ C
1115:→ C
1103:(CHMe
910:NIOSH
462:InChI
419:2587
306:2741
203:ChEBI
144:JSmol
2309:PMID
2103:ISBN
2076:2014
1977:ISBN
1946:ISSN
1911:PMID
1711:ISBN
1678:ISBN
1554:ISBN
1466:IARC
1448:The
1310:and
1212:and
1182:+ H
1178:(OH)
1131:+ H
1023:para
946:IDLH
856:P501
852:P405
844:P391
840:P362
828:P330
824:P321
820:P312
816:P311
796:P280
792:P273
788:P271
784:P270
780:P264
776:P261
762:H400
758:H335
754:H331
750:H319
746:H315
742:H301
574:Odor
395:UNII
368:4650
334:KEGG
323:6307
252:4489
2301:doi
2267:doi
2231:doi
2202:doi
2172:doi
2138:doi
2095:doi
2042:doi
2008:doi
1969:doi
1938:doi
1903:doi
1899:128
1872:doi
1811:doi
1758:doi
1735:doi
1703:doi
1670:doi
1640:doi
1546:doi
1322:or
1255:Q).
1154:: C
933:REL
920:PEL
685:GHS
431:EPA
358:CID
2337::
2315:.
2307:.
2297:11
2295:.
2274:;
2263:35
2261:.
2238:;
2227:54
2225:.
2198:23
2196:.
2168:10
2166:.
2162:.
2134:31
2132:.
2126:.
2101:.
2066:.
2036:.
2015:;
2004:73
2002:.
1975:.
1944:.
1934:72
1932:.
1909:.
1897:.
1884:^
1870:.
1860:24
1858:.
1818:;
1805:.
1769:^
1745:^
1709:.
1701:.
1676:.
1668:.
1647:;
1636:16
1634:.
1620:^
1610:.
1606:.
1588:.
1568:^
1552:.
1529:^
1480:.
1415:Cl
1375:.
1364:.
1239:.
1224:.
1051:,
883:50
881:LD
854:,
850:,
846:,
842:,
838:,
834:,
830:,
826:,
822:,
818:,
814:,
810:,
806:,
802:,
798:,
794:,
790:,
786:,
782:,
778:,
760:,
756:,
752:,
748:,
744:,
689::
2323:.
2303::
2281:.
2269::
2245:.
2233::
2208:.
2204::
2180:.
2174::
2144:.
2140::
2111:.
2097::
2078:.
2048:.
2044::
2038:1
2022:.
2010::
1985:.
1971::
1952:.
1940::
1917:.
1905::
1878:.
1874::
1866::
1825:.
1813::
1807:2
1764:.
1760::
1737::
1719:.
1705::
1686:.
1672::
1654:.
1642::
1562:.
1548::
1421:2
1419:O
1417:4
1413:6
1269:2
1267:O
1265:4
1263:H
1261:6
1253:2
1184:2
1180:2
1176:4
1174:H
1172:6
1168:2
1166:O
1164:2
1160:5
1158:H
1156:6
1135:O
1133:2
1129:2
1125:2
1123:O
1121:4
1119:H
1117:6
1113:2
1109:2
1107:)
1105:2
1101:4
1099:H
1097:6
1095:C
1045:2
1043:O
1041:4
1039:H
1037:6
1035:C
989:N
889:)
885:(
546:2
543:O
540:4
537:H
534:6
531:C
433:)
429:(
146:)
106:p
101:p
20:)
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