24:
46:
338:
209:
37:
638:
633:
721:
725:
782:
724:
726:
23:
856:
1,4-Cyclohexadiene and its derivatives are easily aromatized, the driving force being the formation of an aromatic ring. The conversion to an aromatic system may be used to trigger other reactions, such as the
646:
613:
742:
853:
of related aromatic compounds using an alkali metal dissolved in liquid ammonia and a proton donor such as an alcohol. In this way, over reduction to the fully saturated ring is avoided.
727:
735:
795:
749:
377:
903:
John C. Walton, Fernando
Portela-Cubillo "1,4-Cyclohexadiene" Encyclopedia of Reagents for Organic Synthesis 2007 John Wiley & Sons.
923:
825:. It is a colourless, flammable liquid that is of academic interest as a prototype of a large class of related compounds called
790:
958:
582:
555:
696:
928:
352:
802:
252:
878:
686:
285:
204:
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637:
951:
885:. USA: National Center for Biotechnology Information. 27 March 2005. Identification and Related Records
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838:
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1127:
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904:
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45:
1041:
850:
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36:
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463:
453:
197:
1003:
993:
983:
748:
1018:
1013:
1008:
998:
988:
967:
924:
The photochemistry of 1,4-cyclohexadiene in solution and in the gas phase
761:
734:
741:
422:
217:
177:
849:
In the laboratory, substituted 1,4-cyclohexadienes are synthesized by
830:
826:
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305:
772:
Except where otherwise noted, data are given for materials in their
707:
125:
1101:
443:
261:
666:
1093:
975:
936:
834:
1028:
157:
115:
321:
670:
1140:
273:
723:
101:
674:
952:
361:InChI=1S/C6H8/c1-2-4-6-5-3-1/h1-2,5-6H,3-4H2
959:
945:
844:
336:
207:
185:
817:is an organic compound with the formula C
293:
879:"1,4-cyclohexadiene - Compound Summary"
332:
251:
1141:
198:
940:
458:−50 °C; −58 °F; 223 K
364:Key: UVJHQYIOXKWHFD-UHFFFAOYSA-N
165:
766:−7 °C (19 °F; 266 K)
468:82 °C; 179 °F; 355 K
264:
13:
719:
44:
35:
14:
1160:
917:
966:
780:
636:
631:
412:
22:
776:(at 25 °C , 100 kPa).
897:
871:
406:
1:
933:Reaction thermochemistry data
864:
7:
31:
10:
1165:
909:10.1002/047084289X.rn00806
1115:
1092:
1027:
974:
770:
612:
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505:
393:
373:
348:
85:
75:
63:
58:
30:
21:
687:Precautionary statements
845:Synthesis and reactions
603:-3573.5--3567.5 kJ mol
475:Magnetic susceptibility
930:NIST Chemistry WebBook
730:
49:
40:
829:, an example being γ-
729:
48:
39:
837:of this compound is
712:(fire diamond)
65:Preferred IUPAC name
17:Cyclohexa-1,4-diene
1070:1,4-Cycloheptadiene
1065:1,3-Cycloheptadiene
859:Bergman cyclization
430: g·mol
147:Beilstein Reference
69:Cyclohexa-1,4-diene
18:
1082:1,5-Cyclooctadiene
1055:1,4-Cyclohexadiene
1050:1,3-Cyclohexadiene
839:1,3-cyclohexadiene
815:1,4-Cyclohexadiene
803:Infobox references
731:
253:1,4-cyclohexadiene
80:1,4-Dihydrobenzene
78:1,4-Cyclohexadiene
50:
41:
16:
1136:
1135:
1128:Cyclononatetraene
1123:Cyclooctatetraene
811:Chemical compound
809:
808:
661:Hazard statements
576:63.0-69.2 kJ mol
438:Colorless liquid
317:CompTox Dashboard
127:Interactive image
54:
53:
1156:
1107:Cycloheptatriene
1061:Cycloheptadiene
961:
954:
947:
938:
937:
911:
901:
895:
894:
892:
890:
883:PubChem Compound
875:
793:
787:
784:
783:
751:
744:
737:
722:
702:
698:
694:
680:
676:
672:
668:
640:
635:
599:
572:
545:
521:
506:Thermochemistry
488:Refractive index
481:-48.7·10 cm/mol
429:
414:
408:
401:Chemical formula
341:
340:
325:
323:
297:
277:
266:
255:
236:Gmelin Reference
219:
211:
200:
189:
169:
129:
105:
32:
26:
19:
15:
1164:
1163:
1159:
1158:
1157:
1155:
1154:
1153:
1149:Cyclohexadienes
1139:
1138:
1137:
1132:
1111:
1088:
1046:Cyclohexadiene
1042:Cyclopentadiene
1023:
970:
965:
920:
915:
914:
902:
898:
888:
886:
877:
876:
872:
867:
851:Birch reduction
847:
824:
820:
812:
805:
800:
799:
798: ?)
789:
785:
781:
777:
756:
755:
754:
753:
746:
739:
732:
728:
720:
689:
663:
649:
628:
600:
597:
591:
587:
584:
583:Std enthalpy of
573:
570:
564:
560:
557:
556:Std enthalpy of
549:189.37 J K mol
546:
543:
536:
533:
522:
515:
498:
496:
478:
427:
417:
411:
403:
389:
386:
381:
380:
369:
366:
365:
362:
356:
355:
344:
326:
319:
300:
280:
267:
238:
229:
192:
172:
149:
132:
119:
108:
95:
81:
79:
71:
70:
12:
11:
5:
1162:
1152:
1151:
1134:
1133:
1131:
1130:
1125:
1119:
1117:
1113:
1112:
1110:
1109:
1104:
1098:
1096:
1090:
1089:
1087:
1086:
1085:
1084:
1077:Cyclooctadiene
1074:
1073:
1072:
1067:
1059:
1058:
1057:
1052:
1044:
1039:
1037:Cyclobutadiene
1033:
1031:
1025:
1024:
1022:
1021:
1016:
1011:
1006:
1001:
996:
991:
986:
980:
978:
972:
971:
964:
963:
956:
949:
941:
935:
934:
926:
919:
918:External links
916:
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869:
868:
866:
863:
846:
843:
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810:
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801:
779:
778:
774:standard state
771:
768:
767:
764:
758:
757:
747:
740:
733:
718:
717:
716:
715:
713:
704:
703:
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685:
682:
681:
664:
659:
656:
655:
650:
645:
642:
641:
629:
624:
621:
620:
610:
609:
605:
604:
601:
595:
589:
581:
578:
577:
574:
568:
562:
554:
551:
550:
547:
541:
530:
527:
526:
525:142.2 J K mol
523:
511:
508:
507:
503:
502:
499:
494:
486:
483:
482:
479:
473:
470:
469:
466:
460:
459:
456:
450:
449:
446:
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436:
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431:
425:
419:
418:
415:
409:
404:
399:
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388:
387:
384:
376:
375:
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371:
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367:
363:
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359:
351:
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346:
345:
343:
342:
329:
327:
315:
312:
311:
308:
302:
301:
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298:
290:
288:
282:
281:
279:
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270:
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260:
257:
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249:
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213:
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202:
194:
193:
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182:
180:
174:
173:
171:
170:
162:
160:
154:
153:
150:
145:
142:
141:
138:
137:Abbreviations
134:
133:
131:
130:
122:
120:
113:
110:
109:
107:
106:
98:
96:
91:
88:
87:
83:
82:
77:
73:
72:
68:
67:
61:
60:
56:
55:
52:
51:
42:
28:
27:
9:
6:
4:
3:
2:
1161:
1150:
1147:
1146:
1144:
1129:
1126:
1124:
1121:
1120:
1118:
1114:
1108:
1105:
1103:
1100:
1099:
1097:
1095:
1091:
1083:
1080:
1079:
1078:
1075:
1071:
1068:
1066:
1063:
1062:
1060:
1056:
1053:
1051:
1048:
1047:
1045:
1043:
1040:
1038:
1035:
1034:
1032:
1030:
1026:
1020:
1017:
1015:
1012:
1010:
1007:
1005:
1002:
1000:
997:
995:
992:
990:
987:
985:
982:
981:
979:
977:
973:
969:
962:
957:
955:
950:
948:
943:
942:
939:
932:
931:
927:
925:
922:
921:
910:
906:
900:
884:
880:
874:
870:
862:
860:
854:
852:
842:
840:
836:
832:
828:
816:
804:
797:
792:
775:
769:
765:
763:
760:
759:
752:
745:
738:
714:
711:
710:
706:
705:
691:
688:
684:
683:
665:
662:
658:
657:
654:
651:
648:
644:
643:
639:
634:
630:
627:
623:
622:
618:
616:
611:
606:
602:
594:
586:
580:
579:
575:
567:
559:
553:
552:
548:
540:
535:
529:
528:
524:
519:
514:
513:Heat capacity
510:
509:
504:
500:
493:
489:
485:
484:
480:
476:
472:
471:
467:
465:
464:Boiling point
462:
461:
457:
455:
454:Melting point
452:
451:
447:
445:
442:
441:
437:
434:
433:
426:
424:
421:
420:
405:
402:
398:
397:
392:
383:
382:
379:
372:
358:
357:
354:
347:
339:
335:
334:DTXSID0060854
331:
330:
328:
318:
314:
313:
309:
307:
304:
303:
296:
292:
291:
289:
287:
284:
283:
276:
272:
271:
269:
263:
259:
258:
254:
250:
248:
245:
244:
240:
237:
233:
232:
225:
224:
222:
220:
215:
214:
210:
206:
203:
201:
199:ECHA InfoCard
196:
195:
188:
184:
183:
181:
179:
176:
175:
168:
164:
163:
161:
159:
156:
155:
151:
148:
144:
143:
139:
136:
135:
128:
124:
123:
121:
117:
112:
111:
104:
100:
99:
97:
94:
90:
89:
84:
74:
66:
62:
57:
47:
43:
38:
34:
33:
29:
25:
20:
1004:Cycloheptene
994:Cyclopentene
984:Cyclopropene
968:Cycloalkenes
929:
899:
887:. Retrieved
882:
873:
855:
848:
814:
813:
708:
652:
614:
592:
565:
538:
517:
491:
86:Identifiers
76:Other names
1019:Cyclodecene
1014:Cyclononene
1009:Cyclooctene
999:Cyclohexene
989:Cyclobutene
762:Flash point
647:Signal word
448:0.847 g cm
435:Appearance
394:Properties
205:100.010.040
167:CHEBI:37611
889:12 October
865:References
827:terpenoids
626:Pictograms
585:combustion
423:Molar mass
385:C1C=CCC=C1
295:0F8Z5909QZ
178:ChemSpider
114:3D model (
93:CAS Number
1116:Tetraenes
831:terpinene
701:P308+P313
617:labelling
558:formation
532:Std molar
306:UN number
226:211-043-1
218:EC Number
140:1,4-CHDN
1143:Category
709:NFPA 704
608:Hazards
477:(χ)
152:1900733
103:628-41-1
1102:Benzene
1094:Trienes
976:Alkenes
796:what is
794: (
534:entropy
444:Density
262:PubChem
1029:Dienes
835:isomer
791:verify
788:
653:Danger
501:1.472
428:80.130
378:SMILES
59:Names
833:. An
353:InChI
310:3295
275:12343
241:1656
187:11838
158:ChEBI
116:JSmol
891:2011
697:P210
693:P201
679:H373
675:H350
671:H340
667:H225
286:UNII
247:MeSH
905:doi
615:GHS
596:298
569:298
542:298
322:EPA
265:CID
1145::
881:.
861:.
841:.
699:,
695:,
677:,
673:,
669:,
619::
588:(Δ
561:(Δ
960:e
953:t
946:v
907::
893:.
823:8
821:H
819:6
786:Y
750:0
743:3
736:2
598:)
593:H
590:c
571:)
566:H
563:f
544:)
539:S
537:(
520:)
518:C
516:(
497:)
495:D
492:n
490:(
416:8
413:H
410:6
407:C
324:)
320:(
118:)
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