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
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| 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
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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 edit
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]
Synthesis edit
Bromocyclohexane can be prepared by the free radical bromination of cyclohexane.
Safety edit
Bromocyclohexane is an alkylating agent.
References edit
- ^ Wiederseiner, Sébastien; Andreini, Nicolas; Epely-Chauvin, Gaël; Ancey, Christophe (2011). "Refractive-index and density matching in concentrated particle suspensions: A review" (PDF). Experiments in Fluids. 50 (5): 1183–1206. Bibcode:2011ExFl...50.1183W. doi:10.1007/s00348-010-0996-8. S2CID 33720382.
- ^ "Dielectric Constants of Various Materials". Archived from the original on 2013-11-01. Retrieved 2013-10-30.
- ^ Royall, C. Patrick; Poon, Wilson C. K.; Weeks, Eric R. (2013). "In search of colloidal hard spheres". Soft Matter. 9 (1): 17–27. arXiv:1205.6665. Bibcode:2013SMat....9...17R. doi:10.1039/c2sm26245b. hdl:20.500.11820/0b44579c-35ad-42b2-9be0-1da11c19f3c3. S2CID 54951252.
- ^ Poon, Wilson C. K.; Weeks, Eric R.; Royall, C. Patrick (2012). "On measuring colloidal volume fractions". Soft Matter. 8 (1): 21–30. arXiv:1106.2566. Bibcode:2012SMat....8...21P. doi:10.1039/c1sm06083j. S2CID 23455559.
- ^ Le, Chip; Liang, Yufan; Evans, Ryan W.; Li, Ximing; MacMillan, David W. C. (2017). "Selective sp3 C–H alkylation via polarity-match-based cross-coupling". Nature. 547 (7661): 79–83. Bibcode:2017Natur.547...79L. doi:10.1038/nature22813. PMC 5655994. PMID 28636596.
- ^ Hancock, Evelyn M.; Cope, Arthur C. (1945). "A-Cyclohexylphenylacetonitrile". Organic Syntheses. 25: 25. doi:10.15227/orgsyn.025.0025.