1317:
392:
243:
744:
739:
749:
48:
888:
39:
1012:
891:
893:
892:
1507:
757:
719:
1468:
Polat, K.; Aksu, M.L.; Pekel, A.T. (2002), "Electroreduction of nitrobenzene to p-aminophenol using voltammetric and semipilot scale preparative electrolysis techniques",
894:
902:
1345:
1025:
1620:
916:
1336:
441:
909:
843:
1585:
Anthony S. Travis (2007). "Manufacture and uses of the anilines: A vast array of processes and products". In Zvi
Rappoport (ed.).
1505:, Godfrey, Wilbert & De, Angelis John, "Process of preparing nu-acetyl-p-amino phenol", issued 1961-08-29
1602:
1439:
1410:
1393:
688:
1020:
1637:
1424:
1569:
1451:
Mitchell, S.C. & Waring, R.H. "Aminophenols." In
Ullmann’s Encyclopedia of Industrial Chemistry; 2002 Wiley-VCH,
406:
1032:
1523:"Selective reduction of aromatic nitro compounds with stannous chloride in non acidic and non aqueous medium"
1097:
1096:
Reflecting its slightly hydrophilic character, the white powder is moderately soluble in alcohols and can be
835:
17:
839:
797:
339:
306:
238:
748:
1341:
370:
743:
1377:
1300:
807:
738:
630:
200:
1522:
250:
1303:
used in organic chemistry. Prominently, it is the final intermediate in the industrial synthesis of
1594:
1374:
Nomenclature of
Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)
387:
300:
148:
141:
1173:
1104:
1082:
1685:
1114:
771:
731:
617:
1586:
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66:
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8:
1587:
1242:
1169:
1107:
847:
391:
242:
220:
117:
107:
180:
1485:
1316:
160:
1538:
1633:
1618:
Elmar
Friderichs; Thomas Christoph; Helmut Buschmann. "Analgesics and Antipyretics".
1598:
1565:
1542:
1420:
1389:
671:
569:
1489:
1662:
1625:
1534:
1477:
1452:
1381:
1308:
1280:
1066:
1062:
549:
469:
1629:
1502:
789:
819:
269:
1385:
328:
1354:
1276:
1003:
811:
1481:
952:
1679:
1666:
1546:
1456:
1288:
1261:
1253:
1161:
1136:
1132:
978:
974:
823:
593:
579:
538:
528:
231:
1617:
831:
1265:
1165:
575:
1260:
through a variety of methods, to yield 4-aminophenol. One method involves
915:
1324:
1304:
928:
901:
1328:
908:
607:
560:
497:
251:
211:
1416:
1268:
1157:
803:
359:
1100:
from hot water. In the presence of a base, it oxidizes readily. The
1081:
OH. Typically available as a white powder, it is commonly used as a
1002:
Except where otherwise noted, data are given for materials in their
1241:
It can be produced from nitrobenzene by electrolytic conversion to
874:
289:
867:
785:
147:
140:
47:
1284:
1090:
990:
815:
603:
597:
589:
583:
518:
315:
38:
1153:
1128:
1101:
994:
827:
191:
1332:
1272:
1257:
1160:
followed by reduction with iron. Alternatively, the partial
171:
130:
375:
280:
1652:
1245:, which spontaneously rearranges to 4-aminophenol.
1653:F. B. Dains, Floyd Eberly (1935). "p-Iodophenol".
1408:
777:
1584:
1677:
781:
327:
1172:, which rearranges primarily to 4-aminophenol (
890:
859:
116:
1621:Ullmann's Encyclopedia of Industrial Chemistry
1467:
863:
415:InChI=1S/C6H7NO/c7-5-1-3-6(8)4-2-5/h1-4,8H,7H2
425:InChI=1/C6H7NO/c7-5-1-3-6(8)4-2-5/h1-4,8H,7H2
1559:
1366:
533:187.5 °C (369.5 °F; 460.6 K)
933:195 °C (383 °F; 468 K) (cc)
1476:(2), Kluwer Academic Publishers: 217–223,
855:
390:
241:
219:
1564:. Cambridge: Royal Society of Chemistry.
1520:
1501:
347:
386:
305:
14:
1678:
1353:4-Aminophenol converts readily to the
543:284 °C (543 °F; 557 K)
232:
1521:Bellamy, F. D.; Ou, K. (1984-01-01).
1440:CRC Handbook of Chemistry and Physics
1412:CRC Handbook of Chemistry and Physics
1271:. A second method involves selective
1248:
513:Colorless to reddish-yellow crystals
418:Key: PLIKAWJENQZMHA-UHFFFAOYSA-N
199:
179:
1402:
1236:
1470:Journal of Applied Electrochemistry
428:Key: PLIKAWJENQZMHA-UHFFFAOYAD
318:
288:
24:
1562:Paracetamol: a curriculum resource
1131:aminophenols, the other two being
886:
46:
37:
25:
1697:
1589:The chemistry of Anilines Part 1
1409:Haynes, William M., ed. (2016).
1315:
1010:
747:
742:
737:
487:
481:
1646:
1611:
1006:(at 25 °C , 100 kPa).
1578:
1553:
1514:
1495:
1461:
1445:
1433:
1378:The Royal Society of Chemistry
1339:, B-86810 & B-87836 (c.f.
1307:. Treating 4-aminophenol with
1147:
1142:
490:
475:
13:
1:
1630:10.1002/14356007.a02_269.pub2
1539:10.1016/S0040-4039(01)80041-1
1360:
1127:The compound is one of three
7:
1386:10.1039/9781849733069-FP001
941:or concentration (LD, LC):
33:
10:
1702:
1089:, marketed under the name
1124:are of commercial value.
1000:
963:
937:
718:
713:
681:
664:
602:Negligible solubility in
462:
437:
402:
100:
77:
65:
60:
32:
1667:10.15227/orgsyn.015.0039
1457:10.1002/14356007.a02_099
798:Precautionary statements
1624:. Weinheim: Wiley-VCH.
1482:10.1023/A:1014725116051
1294:
1174:Bamberger rearrangement
897:
51:
42:
1560:Ellis, Frank (2002).
1380:. 2014. p. 690.
1323:It is a precursor to
896:
50:
41:
1152:It is produced from
1122:-dimethylaminophenol
1087:black-and-white film
970:Related aminophenols
879:(fire diamond)
588:Slightly soluble in
67:Preferred IUPAC name
1527:Tetrahedron Letters
1311:gives paracetamol:
1299:4-Aminophenol is a
1243:phenylhydroxylamine
1170:phenylhydroxylamine
550:Solubility in water
505: g·mol
161:Beilstein Reference
29:
1249:From 4-nitrophenol
1111:-methylaminophenol
1033:Infobox references
964:Related compounds
898:
52:
43:
27:
1655:Organic Syntheses
1604:978-0-470-87171-3
1593:. Wiley. p.
1419:. pp. 5–89.
1415:(97th ed.).
1395:978-0-85404-182-4
1285:anhydrous ethanol
1237:From nitrobenzene
1041:Chemical compound
1039:
1038:
986:Related compounds
772:Hazard statements
672:Crystal structure
570:dimethylsulfoxide
371:CompTox Dashboard
149:Interactive image
142:Interactive image
56:
55:
16:(Redirected from
1693:
1671:
1670:
1650:
1644:
1643:
1615:
1609:
1608:
1592:
1582:
1576:
1575:
1557:
1551:
1550:
1518:
1512:
1511:
1510:
1506:
1499:
1493:
1492:
1465:
1459:
1449:
1443:
1437:
1431:
1430:
1406:
1400:
1399:
1370:
1349:
1348:
1344:
1319:
1309:acetic anhydride
1281:Tin(II) Chloride
1063:organic compound
1023:
1017:
1014:
1013:
918:
911:
904:
889:
869:
865:
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857:
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849:
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821:
817:
813:
809:
805:
791:
787:
783:
779:
751:
746:
741:
705:
682:Thermochemistry
653:10.30 (phenol; H
568:Very soluble in
504:
492:
489:
483:
477:
470:Chemical formula
395:
394:
379:
377:
351:
331:
320:
309:
292:
270:Gmelin Reference
253:
245:
234:
223:
203:
183:
151:
144:
120:
34:
30:
26:
21:
1701:
1700:
1696:
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1691:
1690:
1676:
1675:
1674:
1651:
1647:
1640:
1616:
1612:
1605:
1583:
1579:
1572:
1558:
1554:
1519:
1515:
1508:
1500:
1496:
1466:
1462:
1450:
1446:
1438:
1434:
1427:
1407:
1403:
1396:
1372:
1371:
1367:
1363:
1346:
1340:
1297:
1289:ethyl ethanoate
1251:
1239:
1232:
1228:
1224:
1220:
1216:
1207:
1203:
1199:
1195:
1191:
1187:
1183:
1150:
1145:
1080:
1076:
1072:
1042:
1035:
1030:
1029:
1028: ?)
1019:
1015:
1011:
1007:
993:
987:
977:
971:
956:
950:
923:
922:
921:
920:
913:
906:
899:
895:
887:
800:
774:
760:
734:
706:
703:
697:
693:
690:
689:Std enthalpy of
674:
660:
656:
649:
639:
612:
552:
502:
486:
480:
472:
458:
455:
450:
445:
444:
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380:
373:
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334:
321:
295:
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263:
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206:
186:
163:
154:
134:
123:
110:
96:
95:
73:
72:
23:
22:
15:
12:
11:
5:
1699:
1689:
1688:
1673:
1672:
1645:
1639:978-3527306732
1638:
1610:
1603:
1577:
1570:
1552:
1533:(8): 839–842.
1513:
1494:
1460:
1444:
1432:
1426:978-1498754286
1425:
1401:
1394:
1364:
1362:
1359:
1355:diazonium salt
1321:
1320:
1301:building block
1296:
1293:
1250:
1247:
1238:
1235:
1234:
1233:
1230:
1226:
1222:
1218:
1214:
1210:
1209:
1205:
1201:
1197:
1193:
1189:
1185:
1181:
1149:
1146:
1144:
1141:
1098:recrystallized
1078:
1074:
1070:
1040:
1037:
1036:
1031:
1009:
1008:
1004:standard state
1001:
998:
997:
988:
985:
982:
981:
972:
969:
966:
965:
961:
960:
957:
948:
946:
943:
942:
935:
934:
931:
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924:
914:
907:
900:
885:
884:
883:
882:
880:
871:
870:
801:
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775:
770:
767:
766:
761:
756:
753:
752:
735:
730:
727:
726:
716:
715:
711:
710:
709:-190.6 kJ/mol
707:
701:
695:
687:
684:
683:
679:
678:
675:
670:
667:
666:
662:
661:
659:
658:
654:
651:
647:
646:5.48 (amino; H
643:
641:
637:
627:
626:
623:
614:
613:
611:
610:
600:
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572:
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563:
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268:
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261:
257:
255:
247:
246:
236:
228:
227:
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216:
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208:
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205:
204:
196:
194:
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187:
185:
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176:
174:
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167:
164:
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155:
153:
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137:
135:
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125:
124:
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121:
113:
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106:
103:
102:
98:
97:
94:
93:
87:
80:
79:
75:
74:
70:
69:
63:
62:
58:
57:
54:
53:
44:
28:4-Aminophenol
9:
6:
4:
3:
2:
1698:
1687:
1684:
1683:
1681:
1668:
1664:
1660:
1656:
1649:
1641:
1635:
1631:
1627:
1623:
1622:
1614:
1606:
1600:
1596:
1591:
1590:
1581:
1573:
1571:0-85404-375-6
1567:
1563:
1556:
1548:
1544:
1540:
1536:
1532:
1528:
1524:
1517:
1504:
1498:
1491:
1487:
1483:
1479:
1475:
1471:
1464:
1458:
1454:
1448:
1441:
1436:
1428:
1422:
1418:
1414:
1413:
1405:
1397:
1391:
1387:
1383:
1379:
1376:. Cambridge:
1375:
1369:
1365:
1358:
1356:
1351:
1343:
1342:WO 2001042204
1338:
1334:
1330:
1326:
1318:
1314:
1313:
1312:
1310:
1306:
1302:
1292:
1290:
1286:
1282:
1278:
1274:
1270:
1267:
1263:
1262:hydrogenation
1259:
1255:
1254:4-nitrophenol
1246:
1244:
1212:
1211:
1179:
1178:
1177:
1175:
1171:
1167:
1163:
1162:hydrogenation
1159:
1155:
1140:
1138:
1137:3-aminophenol
1134:
1133:2-aminophenol
1130:
1125:
1123:
1121:
1117:
1112:
1110:
1106:
1103:
1099:
1094:
1092:
1088:
1084:
1068:
1064:
1060:
1058:
1053:
1051:
1046:
1045:4-Aminophenol
1034:
1027:
1022:
1005:
999:
996:
992:
989:
984:
983:
980:
979:3-Aminophenol
976:
975:2-Aminophenol
973:
968:
967:
962:
958:
954:
945:
944:
940:
936:
932:
930:
927:
926:
919:
912:
905:
881:
878:
877:
873:
872:
802:
799:
795:
794:
776:
773:
769:
768:
765:
762:
759:
755:
754:
750:
745:
740:
736:
733:
729:
728:
724:
722:
717:
712:
708:
700:
692:
686:
685:
680:
677:orthorhombic
676:
673:
669:
668:
663:
652:
645:
644:
642:
636:
632:
629:
628:
624:
622:
621:
616:
615:
609:
605:
601:
599:
595:
594:diethyl ether
591:
587:
585:
581:
580:ethyl acetate
577:
573:
571:
567:
566:
564:
562:
559:
558:
555:1.5 g/100 mL
554:
551:
547:
546:
542:
540:
539:Boiling point
537:
536:
532:
530:
529:Melting point
527:
526:
522:
520:
517:
516:
512:
509:
508:
501:
499:
496:
495:
474:
471:
467:
466:
461:
452:
447:
446:
443:
436:
422:
412:
411:
408:
401:
393:
389:
388:DTXSID3024499
385:
384:
382:
372:
368:
367:
363:
361:
358:
357:
350:
346:
345:
343:
341:
338:
337:
330:
326:
325:
323:
317:
313:
312:
308:
304:
302:
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:
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170:
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165:
162:
158:
157:
150:
146:
143:
139:
138:
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132:
127:
126:
119:
115:
114:
112:
109:
105:
104:
99:
91:
88:
85:
82:
81:
76:
71:4-Aminophenol
68:
64:
59:
49:
45:
40:
36:
35:
31:
19:
18:P-aminophenol
1686:Aminophenols
1658:
1654:
1648:
1619:
1613:
1588:
1580:
1561:
1555:
1530:
1526:
1516:
1497:
1473:
1469:
1463:
1447:
1435:
1411:
1404:
1373:
1368:
1352:
1337:parapropamol
1322:
1298:
1266:Raney Nickel
1252:
1240:
1166:nitrobenzene
1151:
1126:
1119:
1115:
1108:
1095:
1059:-aminophenol
1056:
1055:
1052:-aminophenol
1049:
1048:
1044:
1043:
938:
875:
763:
720:
698:
634:
619:
576:acetonitrile
454:c1cc(ccc1N)O
449:Oc1ccc(N)cc1
307:Aminophenols
101:Identifiers
92:-Aminophenol
89:
86:-Aminophenol
83:
78:Other names
1325:amodiaquine
1305:paracetamol
1277:nitro group
1148:From phenol
1143:Preparation
1105:derivatives
953:median dose
939:Lethal dose
929:Flash point
758:Signal word
574:Soluble in
510:Appearance
463:Properties
239:100.004.198
181:CHEBI:17602
1503:US2998450A
1361:References
1329:mesalazine
1221:NHOH → HOC
1102:methylated
959:671 mg/kg
732:Pictograms
665:Structure
608:chloroform
561:Solubility
523:1.13 g/cm
498:Molar mass
349:R7P8FRP05V
212:ChemSpider
201:ChEMBL1142
129:3D model (
108:CAS Number
1547:0040-4039
1417:CRC Press
1273:reduction
1158:nitration
1083:developer
1065:with the
848:P308+P313
844:P304+P340
840:P304+P312
836:P301+P312
723:labelling
691:formation
360:UN number
260:204-616-2
252:EC Number
1680:Category
1490:54499902
1442:65th Ed.
1269:catalyst
1204:NHOH + H
1168:affords
1129:isomeric
1061:) is an
876:NFPA 704
714:Hazards
118:123-30-8
1275:of the
1264:over a
1258:reduced
1256:can be
1091:Rodinal
1067:formula
1026:what is
1024: (
991:Aniline
764:Warning
631:Acidity
604:benzene
598:ethanol
590:toluene
584:acetone
519:Density
503:109.128
316:PubChem
166:385836
1661:: 39.
1636:
1601:
1568:
1545:
1509:
1488:
1423:
1392:
1347:
1154:phenol
1021:verify
1018:
995:Phenol
596:, and
582:, and
442:SMILES
290:C02372
192:ChEMBL
61:Names
1486:S2CID
1333:AM404
1192:+ 2 H
625:0.04
407:InChI
364:2512
275:2926
172:ChEBI
131:JSmol
1634:ISBN
1599:ISBN
1566:ISBN
1543:ISSN
1421:ISBN
1390:ISBN
1295:Uses
1135:and
1113:and
1085:for
1050:para
1047:(or
868:P501
864:P405
860:P391
856:P330
852:P312
832:P281
828:P273
824:P271
820:P270
816:P264
812:P261
808:P202
804:P201
790:H410
786:H341
782:H332
778:H302
618:log
606:and
340:UNII
301:MeSH
281:KEGG
90:para
1663:doi
1626:doi
1595:764
1535:doi
1478:doi
1453:doi
1382:doi
1350:).
1291:.
1287:or
1283:in
1279:by
1196:→ C
1176:).
1164:of
1156:by
1054:or
721:GHS
702:298
376:EPA
329:403
319:CID
221:392
1682::
1659:15
1657:.
1632:.
1597:.
1541:.
1531:25
1529:.
1525:.
1484:,
1474:32
1472:,
1388:.
1357:.
1335:,
1331:,
1327:,
1229:NH
1188:NO
1139:.
1093:.
1073:NC
949:50
947:LD
866:,
862:,
858:,
854:,
850:,
846:,
842:,
838:,
834:,
830:,
826:,
822:,
818:,
814:,
810:,
806:,
788:,
784:,
780:,
725::
694:(Δ
657:O)
650:O)
640:)
633:(p
592:,
578:,
1669:.
1665::
1642:.
1628::
1607:.
1574:.
1549:.
1537::
1480::
1455::
1429:.
1398:.
1384::
1231:2
1227:4
1225:H
1223:6
1219:5
1217:H
1215:6
1213:C
1208:O
1206:2
1202:5
1200:H
1198:6
1194:2
1190:2
1186:5
1184:H
1182:6
1180:C
1120:N
1118:,
1116:N
1109:N
1079:4
1077:H
1075:6
1071:2
1069:H
1057:p
1016:Y
955:)
951:(
917:0
910:1
903:2
704:)
699:H
696:f
655:2
648:2
638:a
635:K
620:P
491:O
488:N
485:7
482:H
479:6
476:C
378:)
374:(
133:)
84:p
20:)
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