Bicyclohexyl
Chemical compound
From Wikipedia, the free encyclopedia
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 227 °C (441 °F).
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| Names | |
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| Preferred IUPAC name
1,1′-Bi(cyclohexane) | |
Other names
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| Identifiers | |
3D model (JSmol) |
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.001.966 |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C12H22 | |
| Molar mass | 166.308 g·mol−1 |
| Appearance | Colorless liquid |
| Density | 0.88273 g/cm3 |
| Melting point | 4 °C (39 °F; 277 K) |
| Insoluble | |
| Solubility in other solvents | Miscible with organic solvents |
Refractive index (nD) |
1.4796[1] |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| 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).
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Production
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]
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.[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]
Use
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]