Bromocyclohexane
Chemical compound
From Wikipedia, the free encyclopedia
Bromocyclohexane (also called cyclohexyl bromide, abbreviated CXB) is an organic compound with the chemical formula (CH2)5CHBr.
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| Names | |
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| Preferred IUPAC name
Bromocyclohexane | |
| Other names
Cyclohexyl bromide | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.003.294 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C6H11Br | |
| Molar mass | 163.06 g/mol |
| Appearance | colorless liquid |
| Density | 1.324 g/cm3 |
| Melting point | −57 °C (−71 °F; 216 K) |
| Boiling point | 166 to 167 °C (331 to 333 °F; 439 to 440 K) |
| Hazards | |
| Flash point | 62.8 °C (145.0 °F; 335.9 K) |
| Related compounds | |
Related compounds |
Chlorocyclohexane Fluorocyclohexane Iodocyclohexane |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Uses and reactions
It is used to match the refractive index of PMMA for example in confocal microscopy of colloids. A mixture of cis-decalin and CXB can simultaneously match optical index and density of PMMA.[1] Due to the moderate dielectric constant of CXB (ε = 7.9 [2]), PMMA acquires charges that can be screened by the addition of salt (e.g. tetrabutyl ammonium bromide), leading to a very good approximation of colloidal hard sphere.[3] A drawback is that CXB is a good solvent for PMMA, causing it to swell over time, which may lead to a poor determination of particle radii and determination of solid volume fraction.[4]
It is a standard coupling partner of cross coupling reactions.[5] Similarly, cyclohexyl bromide is a standard alkylating agent.[6]
Stated applications in drug chemistry include the synthesis of gamfexine, drofenine, trihexyphenidyl, procyclidine, feclemine, hexocyclium, hexasonium, amedin & oxyphenonium respectively.
Synthesis
Bromocyclohexane can be prepared by the free radical bromination of cyclohexane.
Safety
Bromocyclohexane is an alkylating agent.