24:
276:
183:
33:
469:
474:
683:
symmetry termed ee anti, and ee gauche. The carbon-carbon bond (pivot) between the rings is 1.55 Å, and the carbon-carbon length in the rings is 1.535 Å and carbon-hydrogen bond length is 1.102 Å. The torsion angle between the rings is 74.9°. The C-C-C bond angle ∠ is about 111° and
847:
Dorofeeva, O.V.; Mastryukov, V.S.; Almenningen, A.; Horn, A.; Klaeboe, P.; Yang, L.; Allinger, N.L. (December 1991). "Molecular structure and conformations of bicyclohexyl, (C6H11)2, as studied by electron diffraction, vibrational spectroscopy and molecular mechanics".
964:
Thoma, M; Schwendler, M; Baltes, H; Helm, C. A; Pfohl, T; Riegler, H; Möhwald, H (1996). "Ellipsometry and X-ray
Reflectivity Studies on Monolayers of Phosphatidylethanolamine and Phosphatidylcholine in Contact with n-Dodecane,n-Hexadecane, and Bicyclohexyl".
482:
449:
540:
883:
Tardajos, G.; Diaz Pena, M.; Lainez, A.; Aicart, E. (October 1986). "Speed of sound in and isothermal compressibility and isobaric expansivity of pure liquids at 298.15 K".
910:
Yue, Lei; Qin, Xiaomei; Wu, Xi; Guo, Yongsheng; Xu, Li; Xie, Hujun; Fang, Wenjun (2 July 2014). "Thermal
Decomposition Kinetics and Mechanism of 1,1′-Bicyclohexyl".
315:
675:
The molecule is not completely flat, and the two rings are twisted compared to each other. Liquid bicyclohexyl contains a mixture of molecules with C
23:
937:
Good, W.D.; Lee, S.H. (July 1976). "The enthalpies of formation of selected naphthalenes, diphenylmethanes, and bicyclic hydrocarbons".
32:
796:
769:
290:
992:
Pujari, Sidharam P; Scheres, Luc; Marcelis, Antonius T. M; Zuilhof, Han (2014). "Covalent
Surface Modification of Oxide Surfaces".
1033:
532:
518:
233:
473:
254:
468:
692:
603:
190:
582:
552:
548:
178:
639:
140:
691:
in bicyclohexyl is 1441.51 m/s, higher than many other hydrocarbons. The density is 882.73 kgm. The
120:
1038:
496:
461:
722:
645:
at room temperature, with a boiling point of 227 °C (441 °F). Its structure consists of two
857:
821:
45:
510:
271:
86:
1009:
792:
786:
765:
759:
718:
1001:
974:
946:
919:
892:
865:
829:
627:
425:
402:
338:
544:
242:
536:
275:
182:
160:
861:
825:
698:
When bicyclohexyl is heated to around 427 °C (801 °F) it slowly decomposes to
96:
688:
597:
1027:
950:
869:
391:
171:
564:
788:
Hydrotreating
Technology for Pollution Control: Catalysts, Catalysis, and Processes
524:
528:
222:
703:
699:
664:
646:
571:
556:
812:
Nixon, A. C.; Thorpe, R. E. (May 1958). "Radiation
Chemistry of Cyclohexane".
413:
360:
151:
660:
can be denitrogenated by hydrogen to yield bicyclohexyl as the main product.
506:
667:
is exposed to radiation, bicyclohexyl is produced among other hydrocarbons.
657:
1013:
1005:
706:, as the pivot bond joining the two rings is the longest and weakest one.
738:
896:
721:
as a building block and structural motif, in studying the chemistry of
381:
209:
191:
978:
923:
833:
502:
642:
131:
596:
Except where otherwise noted, data are given for materials in their
726:
119:
109:
560:
299:
InChI=1S/C12H22/c1-3-7-11(8-4-1)12-9-5-2-6-10-12/h11-12H,1-10H2
259:
695:is 674 TPa and isobaric expansivity is 819 K.
638:and a molecular mass of 166.303 g mol. It is a
221:
95:
649:rings joined by a single carbon-carbon bond.
8:
885:Journal of Chemical & Engineering Data
274:
181:
159:
15:
241:
994:Angewandte Chemie International Edition
750:
709:Heat of combustion is 1814.8 kcal/mol.
320:
295:
270:
939:The Journal of Chemical Thermodynamics
590:245 °C (473 °F; 518 K)
172:
576:92 °C (198 °F; 365 K)
302:Key: WVIIMZNLDWSIRH-UHFFFAOYSA-N
139:
7:
396:4 °C (39 °F; 277 K)
212:
14:
725:, and in surface modification of
472:
467:
350:
31:
22:
814:The Journal of Chemical Physics
791:. CRC Press. pp. 263–265.
600:(at 25 °C , 100 kPa).
419:Miscible with organic solvents
850:Journal of Molecular Structure
344:
1:
951:10.1016/0021-9614(76)90015-X
870:10.1016/0022-2860(91)80071-B
1055:
785:Occelli, Mario L. (1996).
693:isothermal compressibility
764:. Elsevier. p. 214.
717:Bicyclohexyl has uses in
594:
448:
443:
331:
311:
286:
79:
56:
44:
39:
30:
21:
761:Handbook of Hydrocarbons
519:Precautionary statements
1006:10.1002/anie.201306709
758:Ferris, S. W. (2013).
684:C-C-H angle is 109°.
71:Cyclohexylcyclohexane
1034:Cyclohexyl compounds
50:1,1′-Bi(cyclohexane)
46:Preferred IUPAC name
897:10.1021/je00046a031
862:1991JMoSt.263..281D
826:1958JChPh..28.1004N
403:Solubility in water
368: g·mol
18:
912:Energy & Fuels
630:with the formula C
604:Infobox references
416:in other solvents
323:C1CCC(CC1)C2CCCCC2
16:
979:10.1021/la9508194
924:10.1021/ef501077n
834:10.1063/1.1744261
723:liquid interfaces
719:organic synthesis
612:Chemical compound
610:
609:
497:Hazard statements
376:Colorless liquid
255:CompTox Dashboard
121:Interactive image
62:1,1′-Bicyclohexyl
1046:
1018:
1017:
989:
983:
982:
961:
955:
954:
934:
928:
927:
918:(7): 4523–4531.
907:
901:
900:
880:
874:
873:
856:(1–2): 281–297.
844:
838:
837:
820:(5): 1004–1005.
809:
803:
802:
782:
776:
775:
755:
628:organic chemical
618:, also known as
566:
562:
558:
554:
550:
546:
542:
538:
534:
530:
526:
512:
508:
504:
476:
471:
426:Refractive index
367:
352:
346:
339:Chemical formula
279:
278:
263:
261:
245:
225:
214:
193:
185:
174:
163:
143:
123:
99:
35:
26:
19:
1054:
1053:
1049:
1048:
1047:
1045:
1044:
1043:
1024:
1023:
1022:
1021:
1000:(25): 6322–56.
991:
990:
986:
963:
962:
958:
936:
935:
931:
909:
908:
904:
882:
881:
877:
846:
845:
841:
811:
810:
806:
799:
784:
783:
779:
772:
757:
756:
752:
747:
735:
715:
682:
678:
673:
655:
637:
633:
613:
606:
601:
587:
584:
521:
499:
485:
464:
436:
434:
405:
365:
355:
349:
341:
327:
324:
319:
318:
307:
304:
303:
300:
294:
293:
282:
264:
257:
248:
228:
215:
203:
166:
146:
126:
113:
102:
89:
75:
74:
52:
51:
12:
11:
5:
1052:
1050:
1042:
1041:
1036:
1026:
1025:
1020:
1019:
984:
956:
945:(7): 643–650.
929:
902:
891:(4): 492–493.
875:
839:
804:
797:
777:
770:
749:
748:
746:
743:
742:
741:
734:
731:
729:as a solvent.
714:
711:
689:speed of sound
680:
676:
672:
669:
654:
651:
635:
631:
611:
608:
607:
602:
598:standard state
595:
592:
591:
588:
581:
578:
577:
574:
568:
567:
541:P305+P351+P338
522:
517:
514:
513:
500:
495:
492:
491:
486:
481:
478:
477:
465:
460:
457:
456:
446:
445:
441:
440:
437:
432:
424:
421:
420:
417:
410:
409:
406:
401:
398:
397:
394:
388:
387:
384:
378:
377:
374:
370:
369:
363:
357:
356:
353:
347:
342:
337:
334:
333:
329:
328:
326:
325:
322:
314:
313:
312:
309:
308:
306:
305:
301:
298:
297:
289:
288:
287:
284:
283:
281:
280:
267:
265:
253:
250:
249:
247:
246:
238:
236:
230:
229:
227:
226:
218:
216:
208:
205:
204:
202:
201:
197:
195:
187:
186:
176:
168:
167:
165:
164:
156:
154:
148:
147:
145:
144:
136:
134:
128:
127:
125:
124:
116:
114:
107:
104:
103:
101:
100:
92:
90:
85:
82:
81:
77:
76:
73:
72:
69:
66:
63:
59:
58:
54:
53:
49:
48:
42:
41:
37:
36:
28:
27:
13:
10:
9:
6:
4:
3:
2:
1051:
1040:
1037:
1035:
1032:
1031:
1029:
1015:
1011:
1007:
1003:
999:
995:
988:
985:
980:
976:
972:
968:
960:
957:
952:
948:
944:
940:
933:
930:
925:
921:
917:
913:
906:
903:
898:
894:
890:
886:
879:
876:
871:
867:
863:
859:
855:
851:
843:
840:
835:
831:
827:
823:
819:
815:
808:
805:
800:
798:9780824797560
794:
790:
789:
781:
778:
773:
771:9781483272856
767:
763:
762:
754:
751:
744:
740:
737:
736:
732:
730:
728:
724:
720:
712:
710:
707:
705:
701:
696:
694:
690:
685:
670:
668:
666:
661:
659:
652:
650:
648:
644:
641:
629:
625:
624:bicyclohexane
621:
617:
605:
599:
593:
589:
586:
580:
579:
575:
573:
570:
569:
523:
520:
516:
515:
501:
498:
494:
493:
490:
487:
484:
480:
479:
475:
470:
466:
463:
459:
458:
454:
452:
447:
442:
438:
431:
427:
423:
422:
418:
415:
412:
411:
407:
404:
400:
399:
395:
393:
392:Melting point
390:
389:
386:0.88273 g/cm
385:
383:
380:
379:
375:
372:
371:
364:
362:
359:
358:
343:
340:
336:
335:
330:
321:
317:
310:
296:
292:
285:
277:
273:
272:DTXSID8021802
269:
268:
266:
256:
252:
251:
244:
240:
239:
237:
235:
232:
231:
224:
220:
219:
217:
211:
207:
206:
199:
198:
196:
194:
189:
188:
184:
180:
177:
175:
173:ECHA InfoCard
170:
169:
162:
158:
157:
155:
153:
150:
149:
142:
141:ChEMBL1231413
138:
137:
135:
133:
130:
129:
122:
118:
117:
115:
111:
106:
105:
98:
94:
93:
91:
88:
84:
83:
78:
70:
67:
65:Bicyclohexane
64:
61:
60:
55:
47:
43:
38:
34:
29:
25:
20:
17:Bicyclohexyl
1039:Hydrocarbons
997:
993:
987:
970:
966:
959:
942:
938:
932:
915:
911:
905:
888:
884:
878:
853:
849:
842:
817:
813:
807:
787:
780:
760:
753:
727:metal oxides
716:
708:
697:
686:
674:
662:
656:
623:
620:dicyclohexyl
619:
616:Bicyclohexyl
615:
614:
583:Autoignition
488:
450:
429:
80:Identifiers
68:Dicyclohexyl
57:Other names
973:(7): 1722.
704:cyclohexene
700:cyclohexane
665:cyclohexane
647:cyclohexane
640:nonvolatile
585:temperature
572:Flash point
483:Signal word
373:Appearance
332:Properties
179:100.001.966
1028:Categories
745:References
671:Properties
653:Production
462:Pictograms
414:Solubility
408:Insoluble
361:Molar mass
243:Y77501141O
152:ChemSpider
108:3D model (
87:CAS Number
658:Carbazole
553:P337+P313
549:P332+P313
537:P302+P352
453:labelling
200:202-161-4
192:EC Number
1014:24849332
967:Langmuir
739:Biphenyl
733:See also
626:, is an
444:Hazards
858:Bibcode
822:Bibcode
489:Warning
439:1.4796
382:Density
366:166.308
210:PubChem
97:92-51-3
1012:
795:
768:
643:liquid
316:SMILES
132:ChEMBL
40:Names
679:and C
663:When
291:InChI
110:JSmol
1010:PMID
793:ISBN
766:ISBN
702:and
687:The
565:P501
561:P391
557:P362
545:P321
533:P280
529:P273
525:P264
511:H410
507:H319
503:H315
234:UNII
223:7094
161:6827
1002:doi
975:doi
947:doi
920:doi
893:doi
866:doi
854:263
830:doi
713:Use
622:or
451:GHS
260:EPA
213:CID
1030::
1008:.
998:53
996:.
971:12
969:.
941:.
916:28
914:.
889:31
887:.
864:.
852:.
828:.
818:28
816:.
681:2h
636:22
632:12
563:,
559:,
555:,
551:,
547:,
543:,
539:,
535:,
531:,
527:,
509:,
505:,
455::
354:22
348:12
1016:.
1004::
981:.
977::
953:.
949::
943:8
926:.
922::
899:.
895::
872:.
868::
860::
836:.
832::
824::
801:.
774:.
677:2
634:H
435:)
433:D
430:n
428:(
351:H
345:C
262:)
258:(
112:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
