Bromocyclohexane

Bromocyclohexane (also called cyclohexyl bromide, abbreviated CXB) is an organic compound with the chemical formula (CH2)5CHBr.

Bromocyclohexane
Names
Preferred IUPAC name
Bromocyclohexane
Other names
Cyclohexyl bromide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.294
UNII
  • InChI=1S/C6H11Br/c7-6-4-2-1-3-5-6/h6H,1-5H2 checkY
    Key: AQNQQHJNRPDOQV-UHFFFAOYSA-N checkY
  • InChI=1/C6H11Br/c7-6-4-2-1-3-5-6/h6H,1-5H2
    Key: AQNQQHJNRPDOQV-UHFFFAOYAD
  • BrC1CCCCC1
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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Infobox references

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]

Synthesis

Bromocyclohexane can be prepared by the free radical bromination of cyclohexane.

Safety

Bromocyclohexane is an alkylating agent.

References
  1. 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.
  2. "Dielectric Constants of Various Materials". Archived from the original on 2013-11-01. Retrieved 2013-10-30.
  3. 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.
  4. 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.
  5. 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.
  6. Hancock, Evelyn M.; Cope, Arthur C. (1945). "A-Cyclohexylphenylacetonitrile". Organic Syntheses. 25: 25. doi:10.15227/orgsyn.025.0025.
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