Get Bicyclohexyl essential facts below. View Videos or join the Bicyclohexyl discussion. Add Bicyclohexyl to your topic list for future reference or share this resource on social media.
Structural formula of bicyclohexyl
3D ball-and-stick structure of bicyclohexyl
Preferred IUPAC name
Other names
  • 1,1?-Bicyclohexyl
  • Bicyclohexane
  • Dicyclohexyl
  • Cyclohexylcyclohexane
3D model (JSmol)
ECHA InfoCard 100.001.966 Edit this at Wikidata
EC Number
  • 202-161-4
  • InChI=1S/C12H22/c1-3-7-11(8-4-1)12-9-5-2-6-10-12/h11-12H,1-10H2
Molar mass  g·mol-1
Appearance Colorless liquid
Density 0.88273 g/cm3
Melting point 4 °C (39 °F; 277 K)
Solubility in other solvents Miscible with organic solvents
GHS labelling:
GHS07: Exclamation markGHS09: Environmental hazard
H315, H319, H410
P264, P273, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362, P391, P501
Flash point 92 °C (198 °F; 365 K)
245 °C (473 °F; 518 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Bicyclohexyl, also known as dicyclohexyl or bicyclohexane, is an organic chemical with the formula C12H22 and a molecular mass of 166.303 g mol-1. It is a nonvolatile liquid at room temperature, with a boiling point of 227 °C (441 °F). Its structure consists of two cyclohexane rings joined by a single carbon-carbon bond.


Carbazole can be denitrogenated by hydrogen to yield bicyclohexyl as the main product.[2]

When cyclohexane is exposed to radiation, bicyclohexyl is produced among other hydrocarbons.[3]


The molecule is not completely flat, and the two rings are twisted compared to each other. Liquid bicyclohexyl contains a mixture of molecules with C2 and C2h 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 C-C-H angle is 109°.[4]

The speed of sound in bicyclohexyl is 1441.51 m/s, higher than many other hydrocarbons. The density is 882.73 kgm-1. The isothermal compressibility is 674 TPa-1 and isobaric expansivity is 819 K-1.[5]

When bicyclohexyl is heated to around 427 °C (801 °F) it slowly decomposes to cyclohexane and cyclohexene, as the pivot bond joining the two rings is the longest and weakest one.[6]

Heat of combustion is 1814.8 kcal/mol.[7]


Bicyclohexyl has uses in organic synthesis as a building block and structural motif, in studying the chemistry of liquid interfaces,[8] and in surface modification of metal oxides as a solvent.[9]

See also


  1. ^ Ferris, S. W. (2013). Handbook of Hydrocarbons. Elsevier. p. 214. ISBN 9781483272856.
  2. ^ Occelli, Mario L. (1996). Hydrotreating Technology for Pollution Control: Catalysts, Catalysis, and Processes. CRC Press. pp. 263-265. ISBN 9780824797560.
  3. ^ Nixon, A. C.; Thorpe, R. E. (May 1958). "Radiation Chemistry of Cyclohexane". The Journal of Chemical Physics. 28 (5): 1004-1005. doi:10.1063/1.1744261.
  4. ^ 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". Journal of Molecular Structure. 263: 281-297. doi:10.1016/0022-2860(91)80071-B.
  5. ^ 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". Journal of Chemical & Engineering Data. 31 (4): 492-493. doi:10.1021/je00046a031.
  6. ^ 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". Energy & Fuels. 28 (7): 4523-4531. doi:10.1021/ef501077n.
  7. ^ Good, W.D.; Lee, S.H. (July 1976). "The enthalpies of formation of selected naphthalenes, diphenylmethanes, and bicyclic hydrocarbons". The Journal of Chemical Thermodynamics. 8 (7): 643-650. doi:10.1016/0021-9614(76)90015-X.
  8. ^ 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 withn-Dodecane,n-Hexadecane, and Bicyclohexyl". Langmuir. 12 (7): 1722. doi:10.1021/la9508194.
  9. ^ Pujari, Sidharam P; Scheres, Luc; Marcelis, Antonius T. M; Zuilhof, Han (2014). "Covalent Surface Modification of Oxide Surfaces". Angewandte Chemie International Edition. 53 (25): 6322-56. doi:10.1002/anie.201306709. PMID 24849332.

  This article uses material from the Wikipedia page available here. It is released under the Creative Commons Attribution-Share-Alike License 3.0.



Music Scenes