Cyclohexylbenzene is the organic compound with the structural formula C6H5−C6H11. It is a derivative of benzene with a cyclohexyl substituent (C6H11). It is a colorless liquid.
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Preferred IUPAC name
Cyclohexylbenzene | |
Other names
Phenylcyclohexane
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ECHA InfoCard | 100.011.429 |
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CompTox Dashboard (EPA)
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Properties | |
C12H16 | |
Molar mass | 160.260 g·mol−1 |
Appearance | colorless liquid |
Density | 0.982 g/cm3 |
Melting point | 7.3 °C (45.1 °F; 280.4 K) |
Boiling point | 240.1 °C (464.2 °F; 513.2 K) |
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Danger | |
H302, H304, H315, H319, H410 | |
P264, P270, P273, P280, P301+P310, P301+P312, P302+P352, P305+P351+P338, P321, P330, P331, P332+P313, P337+P313, P362, P391, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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Cyclohexylbenzene is produced by the acid-catalyzed alkylation of benzene with cyclohexene.[1][2] The process can proceed using benzene as the exclusive organic precursor. Its partial hydrogenation gives cyclohexene, which alkylates the unhydrogenated benzene.[3]
It is also generated by the hydrodesulfurization of dibenzothiophene.[4]
A route to phenol analogous to the cumene process begins with cyclohexylbenzene, which is oxidized to a hydroperoxide, akin to the production of cumene hydroperoxide. Via the Hock rearrangement, cyclohexylbenzene hydroperoxide cleaves to give phenol and cyclohexanone:
Cyclohexanone is an important precursor to some nylons.[5][3]