Bicyclohexyl


Bicyclohexyl, also known as dicyclohexyl or bicyclohexane, is an organic chemical with the formula C12H22, consisting of two cyclohexane rings joined by a single carbon-carbon bond. It is a nonvolatile liquid at room temperature, with a boiling point of.

Production

Carbazole can be denitrogenated by hydrogen to yield bicyclohexyl as the main product.
When cyclohexane is exposed to radiation, bicyclohexyl is produced among other hydrocarbons.

Properties

In addition to the conformation of each cyclohexane—generally found as a chair—there is conformational variability at the linkage between them. Liquid bicyclohexyl contains a mixture of molecules with C2h and C2 symmetry, termed ee anti and ee gauche, respectively. The link between the two rings has a bond length of 1.55 Å whereas the carbon-carbon length in the rings is around 1.535 Å.
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.
When bicyclohexyl is heated to around it slowly decomposes to cyclohexane and cyclohexene, as the pivot bond joining the two rings is the longest and weakest one.
Heat of combustion is 1814.8 kcal/mol.

Use

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