28:
359:
238:
56:
65:
638:
37:
633:
643:
623:
628:
818:
822:
1009:
823:
1361:
821:
651:
603:
839:
1430:
1610:
1359:, Narisawa, Naoki & Tanaka, Katsutoshi, "Cyclohexanol, method for producing cyclohexanol, and method for producing adipic acid", published 26 Sep 2017
824:
753:
1593:
1285:
1263:
936:
1301:"Complete separation of benzene-cyclohexene-cyclohexane mixtures via temperature-dependent molecular sieving by a flexible chain-like coordination polymer"
1022:
1490:
Reed, Scott M.; Hutchison, James E. (2000). "Green
Chemistry in the Organic Teaching Laboratory: An Environmentally Benign Synthesis of Adipic Acid".
1457:
846:
1552:
Jensen, Frederick R.; Bushweller, C. Hackett (1969). "Conformational preferences and interconversion barriers in cyclohexene and derivatives".
1434:
408:
1299:
Xie, Feng; Chen, Lihang; Cedeño
Morales, Eder Moisés; Ullah, Saif; Fu, Yiwen; Thonhauser, Timo; Tan, Kui; Bao, Zongbi; Li, Jing (2024).
1600:
1647:
1605:
1582:
701:
1474:
1103:
company. The main product of the process is cyclohexane because cyclohexene is more easily hydrogenated than benzene.
1017:
373:
1153:
by acid-catalyzed alkylation with cyclohexene. Cyclohexylbenzene is a precursor to both phenol and cyclohexanone.
1029:
832:
1842:
745:
695:
316:
233:
97:
Tetrahydrobenzene, 1,2,3,4-Tetrahydrobenzene, Benzenetetrahydride, Cyclohex-1-ene, Hexanaphthylene, UN 2256
642:
337:
737:
637:
195:
1640:
1214:. For cyclohexene, however, the alkene is planar, equivalent to an eclipsed conformation at that bond.
960:
947:
632:
1356:
741:
245:
1207:
1199:
869:
354:
566:
622:
1211:
143:
1837:
1633:
1076:
713:
665:
615:
1499:
1312:
1223:
1107:
627:
325:
83:
757:
215:
8:
1758:
1753:
1233:
1228:
119:
109:
1503:
1333:
1316:
1300:
358:
237:
175:
27:
1770:
1743:
1738:
1620:
1176:
721:
155:
55:
1615:
1816:
1811:
1470:
1338:
1184:
1150:
985:
991:
773:
1795:
1561:
1534:
1507:
1462:
1411:
1384:
1328:
1320:
579:
509:
431:
1730:
1161:
882:
729:
289:
264:
64:
709:
1765:
1725:
1324:
1100:
1000:
789:
544:
530:
1589:
1259:
924:
906:
1831:
1538:
1466:
1415:
1388:
1277:
1165:
1092:
687:
498:
488:
226:
679:
36:
1692:
1682:
1672:
1342:
1157:
1111:
1210:
preference for a chair is that it allows each bond of the ring to adopt a
845:
781:
1707:
1702:
1697:
1677:
1656:
1203:
1180:
1169:
1068:
1045:
858:
1565:
831:
761:
749:
1511:
838:
520:
450:
246:
206:
777:
999:
Except where otherwise noted, data are given for materials in their
804:
1587:
1257:
797:
142:
1790:
1096:
725:
478:
276:
1187:
is used as the oxidant in the presence of a tungsten catalyst.
671:
1782:
1664:
1625:
1611:
Reaction of
Cyclohexene with Bromine and Potassium Permanganate
1072:
733:
186:
1374:
1717:
1525:
H. R. Snyder, L. A. Brooks (1932). "1,2-Dibromocyclohexane".
1455:
1282:
Immediately
Dangerous to Life or Health Concentrations (IDLH)
1080:
300:
166:
132:
1401:
705:
342:
973:
468:
1524:
1402:
B. B. Corson, V. N. Ipatieff (1939). "Cyclohexylbenzene".
1298:
717:
683:
1375:
G. H. Coleman, H. F. Johnstone (1925). "Cyclohexene".
1594:
National
Institute for Occupational Safety and Health
1286:
National
Institute for Occupational Safety and Health
1264:
National
Institute for Occupational Safety and Health
769:
1071:. At room temperature, cyclohexene is a colorless
675:
1829:
1551:
288:
820:
785:
118:
1458:Ullmann's Encyclopedia of Industrial Chemistry
1355:
793:
503:82.98 °C (181.36 °F; 356.13 K)
493:−103.5 °C (−154.3 °F; 169.7 K)
1641:
1489:
1202:, unlike the preference for a chair form of
1075:with a sharp odor. Among its uses, it is an
1433:. American Chemical Society. Archived from
1198:Cyclohexene is most stable in a half-chair
1648:
1634:
1601:Material Safety Data Sheet for cyclohexene
1190:Bromination gives 1,2-dibromocyclohexane.
765:
357:
236:
214:
1422:
1332:
1106:In the laboratory, it can be prepared by
382:InChI=1S/C6H10/c1-2-4-6-5-3-1/h1-2H,3-6H2
324:
1588:NIOSH Pocket Guide to Chemical Hazards.
1258:NIOSH Pocket Guide to Chemical Hazards.
392:InChI=1/C6H10/c1-2-4-6-5-3-1/h1-2H,3-6H2
1583:International Chemical Safety Card 1054
1428:
1091:Cyclohexene is produced by the partial
353:
1830:
1454:
1448:
1253:
1251:
1249:
1086:
877:244 °C (471 °F; 517 K)
227:
1629:
1144:
863:−12 °C (10 °F; 261 K)
385:Key: HGCIXCUEYOPUTN-UHFFFAOYSA-N
194:
174:
1246:
395:Key: HGCIXCUEYOPUTN-UHFFFAOYAQ
279:
13:
1431:"What's New in Phenol Production?"
1429:Plotkin, Jeffrey S. (2016-03-21).
816:
63:
54:
35:
26:
14:
1854:
1576:
1655:
1007:
641:
636:
631:
626:
621:
1545:
1518:
1156:Hydration of cyclohexene gives
1079:in the commerical synthesis of
1003:(at 25 °C , 100 kPa).
525:miscible with organic solvents
1483:
1395:
1368:
1349:
1292:
1270:
1:
1239:
1099:, a process developed by the
941:(US health exposure limits):
1193:
7:
1217:
895:or concentration (LD, LC):
50:
22:
10:
1859:
1325:10.1038/s41467-024-46556-6
1208:cyclohexane conformational
515:slightly soluble in water
455:82.143 g/mol
1804:
1781:
1716:
1663:
997:
935:
931:13,196 ppm (mouse, 2 hr)
891:
602:
597:
424:
404:
369:
102:
94:
82:
77:
49:
21:
1621:Data sheet at inchem.org
1539:10.15227/orgsyn.012.0026
1467:10.1002/14356007.a08_217
1416:10.15227/orgsyn.019.0036
1389:10.15227/orgsyn.005.0033
1149:Benzene is converted to
1067:. It is an example of a
967:TWA 300 ppm (1015 mg/m)
954:TWA 300 ppm (1015 mg/m)
696:Precautionary statements
1461:. Weinheim: Wiley-VCH.
913:1407 mg/kg (oral, rat)
567:Magnetic susceptibility
1212:staggered conformation
827:
68:
59:
40:
31:
1616:Cyclohexene synthesis
1305:Nature Communications
1179:of cyclohexene gives
826:
67:
58:
39:
30:
1843:Hydrocarbon solvents
1224:Diels-Alder reaction
1206:. One basis for the
809:(fire diamond)
84:Preferred IUPAC name
1759:1,4-Cycloheptadiene
1754:1,3-Cycloheptadiene
1566:10.1021/ja01049a013
1504:2000JChEd..77.1627R
1317:2024NatCo..15.2240X
1234:Cyclohexa-1,4-diene
1229:Cyclohexa-1,3-diene
1087:Production and uses
510:Solubility in water
156:Beilstein Reference
18:
1771:1,5-Cyclooctadiene
1744:1,4-Cyclohexadiene
1739:1,3-Cyclohexadiene
1512:10.1021/ed077p1627
1177:oxidative cleavage
1145:Reactions and uses
1030:Infobox references
976:(Immediate danger)
828:
69:
60:
41:
32:
16:
1825:
1824:
1817:Cyclononatetraene
1812:Cyclooctatetraene
1560:(21): 5774–5782.
1527:Organic Syntheses
1498:(12): 1627–1629.
1404:Organic Syntheses
1377:Organic Syntheses
1185:Hydrogen peroxide
1168:, a precursor to
1151:cyclohexylbenzene
1048:with the formula
1038:Chemical compound
1036:
1035:
986:Safety data sheet
666:Hazard statements
560:0.022 mol·kg·bar
537:11.9 kPa (25 °C)
535:8.93 kPa (20 °C)
463:colorless liquid
338:CompTox Dashboard
144:Interactive image
73:
72:
45:
44:
1850:
1796:Cycloheptatriene
1750:Cycloheptadiene
1650:
1643:
1636:
1627:
1626:
1606:Safety MSDS data
1597:
1570:
1569:
1554:J. Am. Chem. Soc
1549:
1543:
1542:
1522:
1516:
1515:
1487:
1481:
1480:
1452:
1446:
1445:
1443:
1442:
1426:
1420:
1419:
1399:
1393:
1392:
1372:
1366:
1365:
1364:
1360:
1353:
1347:
1346:
1336:
1296:
1290:
1289:
1274:
1268:
1267:
1255:
1140:
1066:
1020:
1014:
1011:
1010:
925:lowest published
883:Explosive limits
848:
841:
834:
819:
799:
795:
791:
787:
783:
779:
775:
771:
767:
763:
759:
755:
751:
747:
743:
739:
735:
731:
727:
723:
719:
715:
711:
707:
703:
689:
685:
681:
677:
673:
645:
640:
635:
630:
625:
580:Refractive index
573:-57.5·10 cm/mol
432:Chemical formula
362:
361:
346:
344:
328:
292:
281:
265:Gmelin Reference
248:
240:
229:
218:
198:
178:
146:
122:
51:
23:
19:
15:
1858:
1857:
1853:
1852:
1851:
1849:
1848:
1847:
1828:
1827:
1826:
1821:
1800:
1777:
1735:Cyclohexadiene
1731:Cyclopentadiene
1712:
1659:
1654:
1579:
1574:
1573:
1550:
1546:
1523:
1519:
1488:
1484:
1477:
1453:
1449:
1440:
1438:
1427:
1423:
1400:
1396:
1373:
1369:
1362:
1354:
1350:
1297:
1293:
1276:
1275:
1271:
1256:
1247:
1242:
1220:
1196:
1160:, which can be
1147:
1138:
1134:
1130:
1126:
1122:
1118:
1089:
1065:
1061:
1057:
1053:
1049:
1039:
1032:
1027:
1026:
1025: ?)
1016:
1012:
1008:
1004:
977:
964:
951:
928:
922:
910:
904:
874:
871:
853:
852:
851:
850:
843:
836:
829:
825:
817:
698:
668:
654:
618:
590:
588:
570:
557:
555:
546:
512:
444:
440:
434:
420:
417:
412:
411:
400:
397:
396:
393:
387:
386:
383:
377:
376:
365:
347:
340:
331:
311:
295:
282:
267:
258:
221:
201:
181:
158:
149:
136:
125:
112:
98:
90:
89:
12:
11:
5:
1856:
1846:
1845:
1840:
1823:
1822:
1820:
1819:
1814:
1808:
1806:
1802:
1801:
1799:
1798:
1793:
1787:
1785:
1779:
1778:
1776:
1775:
1774:
1773:
1766:Cyclooctadiene
1763:
1762:
1761:
1756:
1748:
1747:
1746:
1741:
1733:
1728:
1726:Cyclobutadiene
1722:
1720:
1714:
1713:
1711:
1710:
1705:
1700:
1695:
1690:
1685:
1680:
1675:
1669:
1667:
1661:
1660:
1653:
1652:
1645:
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1618:
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1608:
1603:
1598:
1585:
1578:
1577:External links
1575:
1572:
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1482:
1476:978-3527306732
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1216:
1195:
1192:
1162:dehydrogenated
1146:
1143:
1142:
1141:
1136:
1132:
1128:
1124:
1120:
1101:Asahi Chemical
1088:
1085:
1063:
1059:
1055:
1051:
1037:
1034:
1033:
1028:
1006:
1005:
1001:standard state
998:
995:
994:
989:
982:
981:
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969:
968:
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754:P303+P361+P353
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531:Vapor pressure
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1501:
1497:
1493:
1492:J. Chem. Educ
1486:
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1437:on 2019-10-27
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1326:
1322:
1318:
1314:
1310:
1306:
1302:
1295:
1287:
1283:
1279:
1278:"Cyclohexene"
1273:
1265:
1261:
1254:
1252:
1250:
1245:
1235:
1232:
1230:
1227:
1225:
1222:
1221:
1215:
1213:
1209:
1205:
1201:
1191:
1188:
1186:
1182:
1178:
1173:
1171:
1167:
1166:cyclohexanone
1163:
1159:
1154:
1152:
1117:
1116:
1115:
1113:
1109:
1104:
1102:
1098:
1094:
1093:hydrogenation
1084:
1082:
1078:
1074:
1070:
1047:
1043:
1031:
1024:
1019:
1002:
996:
993:
992:External MSDS
990:
987:
984:
983:
979:
975:
971:
970:
966:
963:(Recommended)
962:
958:
957:
953:
950:(Permissible)
949:
945:
944:
940:
939:
934:
930:
926:
917:
916:
912:
908:
899:
898:
894:
890:
887:0.8–5 %
886:
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1838:Cycloalkenes
1693:Cycloheptene
1687:
1683:Cyclopentene
1673:Cyclopropene
1657:Cycloalkenes
1557:
1553:
1547:
1530:
1526:
1520:
1495:
1491:
1485:
1456:
1450:
1439:. Retrieved
1435:the original
1424:
1407:
1403:
1397:
1380:
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1370:
1351:
1308:
1304:
1294:
1281:
1272:
1200:conformation
1197:
1189:
1174:
1158:cyclohexanol
1155:
1148:
1112:cyclohexanol
1105:
1090:
1077:intermediate
1041:
1040:
937:
892:
870:Autoignition
805:
657:
604:
583:
550:
536:
483:0.8110 g/cm
301:RTECS number
103:Identifiers
95:Other names
17:Cyclohexene
1708:Cyclodecene
1703:Cyclononene
1698:Cyclooctene
1688:Cyclohexene
1678:Cyclobutene
1311:(1): 2240.
1204:cyclohexane
1181:adipic acid
1170:caprolactam
1108:dehydration
1069:cycloalkene
1046:hydrocarbon
1042:Cyclohexene
907:median dose
893:Lethal dose
872:temperature
859:Flash point
652:Signal word
545:Henry's law
460:Appearance
425:Properties
234:100.003.462
196:ChEMBL16396
176:CHEBI:36404
88:Cyclohexene
1832:Categories
1441:2018-01-02
1357:US 9771313
1240:References
1127:OH → C
616:Pictograms
521:Solubility
451:Molar mass
326:12L0P8F7GN
207:ChemSpider
131:3D model (
110:CAS Number
1805:Tetraenes
1194:Structure
980:2000 ppm
790:P403+P235
782:P370+P378
750:P302+P352
746:P301+P312
742:P301+P310
607:labelling
416:C1CCC=CC1
308:GW2500000
255:203-807-8
247:EC Number
1596:(NIOSH).
1343:38472202
1334:10933443
1288:(NIOSH).
1266:(NIOSH).
1218:See also
1164:to give
806:NFPA 704
598:Hazards
569:(χ)
547:constant
120:110-83-8
1791:Benzene
1783:Trienes
1665:Alkenes
1590:"#0167"
1500:Bibcode
1313:Bibcode
1260:"#0167"
1097:benzene
1023:what is
1021: (
593:1.4465
549: (
479:Density
445:
277:PubChem
161:906737
1718:Dienes
1533:: 26.
1473:
1410:: 36.
1383:: 33.
1363:
1341:
1331:
1073:liquid
1018:verify
1015:
988:(SDS)
658:Danger
473:sweet
409:SMILES
187:ChEMBL
78:Names
1081:nylon
1044:is a
938:NIOSH
374:InChI
270:1659
167:ChEBI
133:JSmol
1471:ISBN
1339:PMID
1175:The
1135:+ H
974:IDLH
798:P501
794:P405
786:P391
778:P363
774:P361
770:P331
766:P330
762:P322
758:P312
738:P280
734:P273
730:P270
726:P264
722:P243
718:P242
714:P241
710:P240
706:P233
702:P210
688:H411
684:H311
680:H305
676:H302
672:H225
469:Odor
317:UNII
290:8079
216:7788
1562:doi
1535:doi
1508:doi
1463:doi
1412:doi
1385:doi
1329:PMC
1321:doi
1110:of
1095:of
1050:(CH
961:REL
948:PEL
605:GHS
343:EPA
280:CID
1834::
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1558:91
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1531:12
1529:.
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1494:.
1469:.
1408:19
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1284:.
1280:.
1262:.
1248:^
1183:.
1172:.
1133:10
1125:11
1114:.
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921:Lo
919:LC
903:50
901:LD
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792:,
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780:,
776:,
772:,
768:,
764:,
760:,
756:,
752:,
748:,
744:,
740:,
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732:,
728:,
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720:,
716:,
712:,
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704:,
686:,
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1391:.
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1137:2
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1129:6
1123:H
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1119:C
1064:2
1062:H
1060:2
1058:C
1056:4
1054:)
1052:2
1013:Y
927:)
923:(
909:)
905:(
847:0
840:3
833:1
589:)
587:D
584:n
582:(
556:)
554:H
551:k
441:H
439:6
437:C
345:)
341:(
135:)
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