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Nitrobenzene

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1143: 1286: 377: 236: 792: 605: 600: 49: 65: 788: 1124: 39: 1151: 1382:, weakness in the arms and legs, and in rare cases may be fatal. The oil is readily absorbed through the skin and may increase heart rate, cause convulsions or rarely death. Ingestion may similarly cause headaches, dizziness, nausea, vomiting and gastrointestinal irritation, loss of sensation/use in limbs and also causes internal bleeding. 996: 1118: 793: 791: 613: 580: 809: 1453:
Ahluwalia, R.; Wanchoo, R. K.; Sharma, S. K.; Vashisht, J. L. (1996). "Density, viscosity, and surface tension of binary liquid systems: Ethanoic acid, propanoic acid, and butanoic acid with nitrobenzene".
1109:. This mixture is sometimes called "mixed acid." The production of nitrobenzene is one of the most dangerous processes conducted in the chemical industry because of the exothermicity of the reaction (Δ 1142: 1609:
Bhattacharya A, Purohit VC, Suarez V, Tichkule R, Parmer G, Rinaldi F (March 2006). "One-step reductive amidation of nitro arenes: application in the synthesis of Acetaminophen".
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reaction of it with benzene. The nitronium ion is generated by the reaction of nitric acid and an acidic dehydration agent, typically sulfuric acid:
1312:. It has been replaced by less toxic chemicals for this purpose. A significant merchant market for nitrobenzene is its use in the production of the 719: 1378:, impair vision, cause liver or kidney damage, anemia and lung irritation. Inhalation of vapors may induce headache, nausea, fatigue, dizziness, 1899: 1397: 1544: 1404:(42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities. 1988: 1176: 1983: 1393:
which is "possibly carcinogenic to humans". It has been shown to cause liver, kidney, and thyroid adenomas and carcinomas in rats.
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Nitrobenzene is considered a likely human carcinogen by the United States Environmental Protection Agency, and is classified by the
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Karwa, Shrikant L.; Rajadhyaksha, Rajeev A. (January 1988). "Selective catalytic hydrogenation of nitrobenzene to hydrazobenzene".
1823: 141: 703: 675: 711: 665: 334: 604: 1900:"40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" 355: 759: 802: 1993: 1016: 935: 922: 1285: 1998: 1308:, and other materials. Redistilled, as oil of mirbane, nitrobenzene had been used as an inexpensive perfume for 974: 243: 839: 653: 1862: 1978: 731: 553: 723: 231: 1973: 1886: 1368: 627: 599: 592: 193: 48: 751: 1910: 77: 1352: 1304:
Nitrobenzene is used to mask unpleasant odors in shoe and floor polishes, leather dressings, paint
691: 372: 107: 1479: 1290: 683: 657: 153: 1066:-like odor. It freezes to give greenish-yellow crystals. It is produced on a large scale from 735: 679: 1948: 695: 1842: 1777: 1753: 1714: 1683: 1591: 1540: 1471: 1032: 707: 38: 1745: 1659: 1618: 1581: 1573: 1532: 1463: 1043: 531: 449: 739: 343: 1356: 852: 743: 715: 262: 213: 1938: 727: 755: 649: 376: 235: 173: 117: 1863:"Agents Classified by the IARC Monographs, International Agency for Research on Cancer" 1586: 1561: 1375: 1348: 1344: 1277: 1056: 1035: 987: 978: 671: 542: 64: 1967: 1098: 1079: 1039: 520: 510: 224: 1483: 767: 1336: 1327:. Evidence suggests its use in agriculture as a plant growth/flowering stimulant. 1253: 1205: 687: 1123: 1622: 1335:
Aside from its conversion to aniline, nitrobenzene can be selectively reduced to
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National Institutes of Health · U.S. Department of Health and Human Services,
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Except where otherwise noted, data are given for materials in their
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Immediately Dangerous to Life or Health Concentrations (IDLH)
1355:. It has been used as a mild oxidant in reactions like the 1319:(also known as acetaminophen). Nitrobenzene is also used in 1156:
World capacity for nitrobenzene in 1985 was about 1,700,000
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Division, US EPA, ORD, Integrated Risk Information System.
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in the United States as defined in Section 302 of the U.S.
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Prolonged exposure may cause serious damage to the central
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Approximately 95% of nitrobenzene industrially produced is
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Bigelow, H. E.; Palmer, Albert (1931). "Azoxybenzene".
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National Institute for Occupational Safety and Health
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National Institute for Occupational Safety and Health
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5 mg/m) and readily absorbed through the skin.
1074:. In the laboratory, it is occasionally used as a 1062:. It is a water-insoluble pale yellow oil with an 1402:Emergency Planning and Community Right-to-Know Act 1824:"Nitrobenzene CASRN 98-95-3 - IRIS - US EPA, ORD" 306: 1738:Industrial & Engineering Chemistry Research 790: 495:pungent, like paste shoe polish to almond-like 116: 1529:Ullmann's Encyclopedia of Industrial Chemistry 1289:Most aniline is consumed in the production of 1703: 1701: 1527:Booth G (2007). "Nitro Compounds, Aromatic". 8: 1847:: CS1 maint: multiple names: authors list ( 525:210.9 °C (411.6 °F; 484.0 K) 1959:https://patents.google.com/patent/US9113628 400:InChI=1S/C6H5NO2/c8-7(9)6-4-2-1-3-5-6/h1-5H 1097:of benzene with a mixture of concentrated 410:InChI=1/C6H5NO2/c8-7(9)6-4-2-1-3-5-6/h1-5H 375: 234: 212: 26: 1887:Nomination: Nitrobenzene Review committee 1585: 515:5.7 °C (42.3 °F; 278.8 K) 342: 1434:NIOSH Pocket Guide to Chemical Hazards. 1939:International Chemical Safety Card 0065 1522: 1520: 1518: 1413: 431: 396: 371: 1944:NIOSH Pocket Guide to Chemical Hazards 1840: 1495: 1493: 1429: 1427: 1425: 1423: 1421: 1419: 1417: 847:480 °C (896 °F; 753 K) 225: 1708:Coleman GH, McCloskey CM, Stuart FA. 1531:(6th ed.). Weinheim: Wiley-VCH. 833:88 °C (190 °F; 361 K) 403:Key: LQNUZADURLCDLV-UHFFFAOYSA-N 192: 172: 7: 1177:electrophilic aromatic substitution 413:Key: LQNUZADURLCDLV-UHFFFAOYAA 297: 281: 1167:process involves formation of the 25: 1677:Bigelow HE, Robinson DB (1955). 1149: 1141: 1122: 1116: 994: 603: 598: 63: 1323:, as it has an unusually large 1293:, a precursor to polyurethanes. 990:(at 25 °C , 100 kPa). 1949:IARC Monograph: "Nitrobenzene" 1367:Nitrobenzene is highly toxic ( 1: 1456:Journal of Solution Chemistry 1398:extremely hazardous substance 916:(US health exposure limits): 1623:10.1016/j.tetlet.2005.09.196 1093:Nitrobenzene is prepared by 1989:Nonlinear optical materials 1560:Hogarth CW (January 1912). 865:or concentration (LD, LC): 33: 2015: 1907:Government Printing Office 1787:, vol. 1, p. 445 1724:, vol. 3, p. 668 1693:, vol. 3, p. 103 1357:Skraup quinoline synthesis 1252:Aniline is a precursor to 477:123.11 g/mol 1984:IARC Group 2B carcinogens 1905:(July 1, 2008 ed.). 984: 975:Benzenediazonium chloride 959: 910: 861: 579: 574: 442: 422: 387: 100: 88: 76: 71: 62: 32: 1664:10.15227/orgsyn.011.0016 1537:10.1002/14356007.a17_411 1300:Specialized applications 1038:and the simplest of the 666:Precautionary statements 1799:Clarke, HT; Davis, AW. 1773:"β-Phenylhydroxylamine" 1566:British Medical Journal 1396:It is classified as an 887:590 mg/kg (mouse, oral) 554:Magnetic susceptibility 537:0.19 g/100 ml at 20 °C 485:yellowish, oily liquid 1578:10.1136/bmj.1.2665.183 1294: 906:750 mg/kg (dog, oral) 797: 53: 43: 1369:Threshold Limit Value 1288: 885:600 mg/kg (rat, oral) 883:780 mg/kg (rat, oral) 796: 51: 41: 1916:on February 25, 2012 942:TWA 1 ppm (5 mg/m) 929:TWA 1 ppm (5 mg/m) 779:(fire diamond) 78:Preferred IUPAC name 1750:10.1021/ie00073a005 1611:Tetrahedron Letters 1391:Group 2B carcinogen 1353:phenylhydroxylamine 532:Solubility in water 154:Beilstein Reference 29: 1468:10.1007/BF00972581 1295: 1291:methylenedianiline 1175:), followed by an 1070:as a precursor to 1017:Infobox references 960:Related compounds 951:(Immediate danger) 798: 54: 44: 27: 1994:Aromatic solvents 1805:Organic Syntheses 1785:Collected Volumes 1778:Organic Syntheses 1722:Collected Volumes 1715:Organic Syntheses 1691:Collected Volumes 1684:Organic Syntheses 1652:Organic Syntheses 1617:(11): 1861–1864. 1546:978-3-527-30385-4 1331:Organic reactions 1078:, especially for 1025:Chemical compound 1023: 1022: 966:Related compounds 628:Hazard statements 560:-61.80·10 cm/mol 356:CompTox Dashboard 142:Interactive image 58: 57: 16:(Redirected from 2006: 1999:Phenyl compounds 1954:US EPA factsheet 1926: 1925: 1923: 1921: 1915: 1909:. Archived from 1904: 1896: 1890: 1883: 1877: 1876: 1874: 1872: 1867: 1859: 1853: 1852: 1846: 1838: 1836: 1834: 1819: 1813: 1812: 1796: 1790: 1788: 1781: 1768: 1762: 1761: 1733: 1727: 1725: 1718: 1710:"Nitrosobenzene" 1705: 1696: 1694: 1687: 1674: 1668: 1667: 1647: 1641: 1640: 1633: 1627: 1626: 1606: 1600: 1599: 1589: 1557: 1551: 1550: 1524: 1513: 1512: 1497: 1488: 1487: 1450: 1444: 1443: 1431: 1154: 1153: 1145: 1135: 1126: 1120: 1113:= −117 kJ/mol). 1044:chemical formula 1007: 1001: 998: 997: 900:lowest published 853:Explosive limits 818: 811: 804: 789: 769: 765: 761: 757: 753: 749: 745: 741: 737: 733: 729: 725: 721: 717: 713: 709: 705: 701: 697: 693: 689: 685: 681: 677: 673: 659: 655: 651: 647: 643: 639: 635: 607: 602: 547:0.3 mmHg (25°C) 450:Chemical formula 380: 379: 364: 362: 346: 310: 299: 285: 263:Gmelin Reference 246: 238: 227: 216: 196: 176: 144: 120: 67: 34: 30: 21: 18:Mononitrobenzene 2014: 2013: 2009: 2008: 2007: 2005: 2004: 2003: 1964: 1963: 1935: 1930: 1929: 1919: 1917: 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1997: 1995: 1992: 1990: 1987: 1985: 1982: 1980: 1977: 1975: 1974:Nitrobenzenes 1972: 1971: 1969: 1960: 1957: 1955: 1952: 1950: 1947: 1945: 1942: 1940: 1937: 1936: 1932: 1912: 1908: 1901: 1895: 1892: 1888: 1882: 1879: 1864: 1858: 1855: 1850: 1844: 1829: 1828:cfpub.epa.gov 1825: 1818: 1815: 1810: 1806: 1802: 1795: 1792: 1786: 1780: 1779: 1774: 1767: 1764: 1759: 1755: 1751: 1747: 1743: 1739: 1732: 1729: 1723: 1717: 1716: 1711: 1704: 1702: 1698: 1692: 1686: 1685: 1680: 1673: 1670: 1665: 1661: 1657: 1653: 1646: 1643: 1638: 1632: 1629: 1624: 1620: 1616: 1612: 1605: 1602: 1597: 1593: 1588: 1583: 1579: 1575: 1572:(2665): 183. 1571: 1567: 1563: 1556: 1553: 1548: 1542: 1538: 1534: 1530: 1523: 1521: 1519: 1515: 1510: 1506: 1502: 1496: 1494: 1490: 1485: 1481: 1477: 1473: 1469: 1465: 1461: 1457: 1449: 1446: 1441: 1437: 1430: 1428: 1426: 1424: 1422: 1420: 1418: 1414: 1407: 1405: 1403: 1399: 1394: 1392: 1388: 1383: 1381: 1377: 1372: 1370: 1362: 1360: 1358: 1354: 1350: 1346: 1342: 1338: 1330: 1328: 1326: 1325:Kerr constant 1322: 1318: 1315: 1311: 1307: 1299: 1292: 1287: 1283: 1282: 1281: 1279: 1275: 1271: 1267: 1263: 1259: 1255: 1215: 1214: 1213: 1211: 1207: 1199: 1182: 1181: 1180: 1178: 1170: 1166: 1161: 1159: 1152: 1144: 1125: 1119: 1114: 1112: 1108: 1104: 1100: 1099:sulfuric acid 1096: 1088: 1086: 1084: 1081: 1080:electrophilic 1077: 1073: 1069: 1065: 1061: 1055: 1045: 1041: 1040:nitrobenzenes 1037: 1034: 1030: 1018: 1011: 1006: 989: 983: 980: 976: 972: 969: 964: 963: 958: 954: 950: 946: 945: 941: 938:(Recommended) 937: 933: 932: 928: 925:(Permissible) 924: 920: 919: 915: 914: 909: 905: 901: 892: 891: 882: 878: 869: 868: 864: 860: 856: 854: 851: 850: 846: 843: 837: 836: 832: 830: 827: 826: 819: 812: 805: 781: 778: 777: 773: 772: 670: 667: 663: 662: 632: 629: 625: 624: 621: 618: 615: 611: 610: 606: 601: 597: 594: 590: 589: 585: 583: 578: 573: 570:1.8112 mPa·s 569: 567: 564: 563: 559: 555: 551: 550: 546: 544: 541: 540: 536: 533: 529: 528: 524: 522: 521:Boiling point 519: 518: 514: 512: 511:Melting point 509: 508: 504: 502: 499: 498: 494: 492: 489: 488: 484: 481: 480: 476: 474: 471: 470: 454: 451: 447: 446: 441: 432: 428: 421: 407: 397: 393: 386: 378: 374: 373:DTXSID3020964 370: 369: 367: 357: 353: 352: 345: 341: 340: 338: 336: 333: 332: 325: 324: 322: 320: 317: 316: 309: 305: 304: 302: 296: 292: 291: 284: 280: 279: 277: 275: 272: 271: 267: 264: 260: 259: 252: 251: 249: 247: 242: 241: 237: 233: 230: 228: 226:ECHA InfoCard 223: 222: 215: 211: 210: 208: 206: 203: 202: 195: 191: 190: 188: 186: 183: 182: 175: 171: 170: 168: 166: 163: 162: 158: 155: 151: 150: 143: 139: 138: 136: 132: 127: 126: 119: 115: 114: 112: 109: 105: 104: 99: 87: 79: 75: 70: 66: 61: 50: 46: 40: 36: 35: 31: 28:Nitrobenzene 19: 1918:. Retrieved 1911:the original 1894: 1889:, 02/02/2010 1881: 1869:. Retrieved 1857: 1831:. Retrieved 1827: 1817: 1808: 1804: 1794: 1784: 1776: 1766: 1744:(1): 21–24. 1741: 1737: 1731: 1721: 1713: 1690: 1682: 1679:"Azobenzene" 1672: 1655: 1651: 1645: 1631: 1614: 1610: 1604: 1569: 1565: 1555: 1528: 1504: 1459: 1455: 1448: 1395: 1384: 1373: 1366: 1337:azoxybenzene 1334: 1303: 1251: 1206:hydrogenated 1203: 1187:+ H ⇌ NO 1162: 1155: 1110: 1092: 1029:Nitrobenzene 1028: 1027: 912: 862: 840:Autoignition 775: 619: 581: 319:RTECS number 101:Identifiers 89:Other names 82:Nitrobenzene 52:Nitrobenzene 42:Nitrobenzene 1920:October 29, 1801:"Quinoline" 1317:paracetamol 1260:chemicals, 1107:nitric acid 1042:, with the 877:median dose 863:Lethal dose 842:temperature 829:Flash point 614:Signal word 505:1.199 g/cm 482:Appearance 443:Properties 232:100.002.469 194:ChEMBL15750 174:CHEBI:27798 91:Nitrobenzol 1968:Categories 1408:References 1341:azobenzene 1321:Kerr cells 1274:explosives 1262:pesticides 1256:polymers, 1089:Production 593:Pictograms 473:Molar mass 344:E57JCN6SSY 205:ChemSpider 129:3D model ( 108:CAS Number 1871:10 August 1833:10 August 1758:0888-5885 1476:0095-9782 1314:analgesic 1169:nitronium 1165:nitration 1095:nitration 760:P403+P233 724:P308+P313 720:P304+P340 716:P302+P352 712:P301+P310 584:labelling 566:Viscosity 326:DA6475000 253:202-716-0 245:EC Number 1843:cite web 1771:Kamm O. 1596:20765985 1511:(NIOSH). 1484:95126469 1442:(NIOSH). 1380:cyanosis 1306:solvents 1270:azo dyes 1254:urethane 1083:reagents 1033:aromatic 955:200 ppm 776:NFPA 704 575:Hazards 556:(χ) 1587:2344391 1436:"#0450" 1351:, and 1210:aniline 1171:ion (NO 1134:  1076:solvent 1072:aniline 1068:benzene 1010:what is 1008: ( 971:Aniline 857:1.8%-? 501:Density 467: 295:PubChem 159:507540 118:98-95-3 1811:: 478. 1756:  1658:: 16. 1594:  1584:  1543:  1482:  1474:  1363:Safety 1276:, and 1258:rubber 1244:+ 2 H 1228:+ 3 H 1158:tonnes 1130:  1105:, and 1064:almond 1031:is an 1005:verify 1002:  620:Danger 427:SMILES 283:C06813 268:50357 185:ChEMBL 72:Names 1914:(PDF) 1903:(PDF) 1866:(PDF) 1480:S2CID 1389:as a 1310:soaps 1232:→ C 1103:water 913:NIOSH 392:InChI 165:ChEBI 131:JSmol 1922:2011 1873:2017 1849:link 1835:2017 1754:ISSN 1592:PMID 1541:ISBN 1472:ISSN 1387:IARC 1266:dyes 1200:Uses 1191:+ H 1163:The 949:IDLH 768:P501 764:P405 756:P363 752:P361 748:P330 744:P322 740:P321 736:P314 732:P312 728:P311 708:P281 704:P280 700:P273 696:P271 692:P270 688:P264 684:P261 680:P260 676:P202 672:P201 658:H412 654:H372 650:H360 646:H351 642:H331 638:H311 634:H301 491:Odor 335:UNII 308:7416 274:KEGG 214:7138 1746:doi 1660:doi 1619:doi 1582:PMC 1574:doi 1533:doi 1464:doi 1272:), 1212:: 1208:to 1183:HNO 936:REL 923:PEL 582:GHS 361:EPA 298:CID 1970:: 1845:}} 1841:{{ 1826:. 1807:. 1803:. 1782:; 1775:. 1752:. 1742:27 1740:. 1719:; 1712:. 1700:^ 1688:; 1681:. 1656:11 1654:. 1615:47 1613:. 1590:. 1580:. 1568:. 1564:. 1539:. 1517:^ 1507:. 1503:. 1492:^ 1478:. 1470:. 1460:25 1458:. 1438:. 1416:^ 1359:. 1347:, 1343:, 1339:, 1280:. 1264:, 1240:NH 1224:NO 1160:. 1121:+ 1101:, 1085:. 1057:NO 896:Lo 894:LD 873:50 871:LD 766:, 762:, 758:, 754:, 750:, 746:, 742:, 738:, 734:, 730:, 726:, 722:, 718:, 714:, 710:, 706:, 702:, 698:, 694:, 690:, 686:, 682:, 678:, 674:, 656:, 652:, 648:, 644:, 640:, 636:, 586:: 463:NO 1924:. 1875:. 1851:) 1837:. 1809:1 1789:. 1760:. 1748:: 1726:. 1695:. 1666:. 1662:: 1639:. 1625:. 1621:: 1598:. 1576:: 1570:1 1549:. 1535:: 1486:. 1466:: 1248:O 1246:2 1242:2 1238:5 1236:H 1234:6 1230:2 1226:2 1222:5 1220:H 1218:6 1216:C 1195:O 1193:2 1189:2 1185:3 1173:2 1136:H 1111:H 1059:2 1053:5 1051:H 1049:6 1047:C 1000:N 902:) 898:( 879:) 875:( 817:1 810:2 803:3 465:2 461:5 459:H 457:6 455:C 363:) 359:( 133:) 20:)

Index

Mononitrobenzene
Nitrobenzene
Nitrobenzene

Preferred IUPAC name
CAS Number
98-95-3
JSmol
Interactive image
Beilstein Reference
ChEBI
CHEBI:27798
ChEMBL
ChEMBL15750
ChemSpider
7138
ECHA InfoCard
100.002.469
Edit this at Wikidata
EC Number
Gmelin Reference
KEGG
C06813
PubChem
7416
RTECS number
UNII
E57JCN6SSY
CompTox Dashboard
DTXSID3020964

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