Bromocyclohexane Explained

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

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.

Notes and References

  1. 10.1007/s00348-010-0996-8 . Refractive-index and density matching in concentrated particle suspensions: A review . 2011 . Wiederseiner . Sébastien . Andreini . Nicolas . Epely-Chauvin . Gaël . Ancey . Christophe . Experiments in Fluids . 50 . 5 . 1183–1206 . 2011ExFl...50.1183W . 33720382 .
  2. Web site: Dielectric Constants of Various Materials . 2013-10-30 . https://web.archive.org/web/20131101180301/http://www.deltacnt.com/99-00032.htm . 2013-11-01 . dead .
  3. 10.1039/c2sm26245b . In search of colloidal hard spheres . 2013 . Royall . C. Patrick . Poon . Wilson C. K. . Weeks . Eric R. . Soft Matter . 9 . 1 . 17–27 . 1205.6665 . 2013SMat....9...17R . 20.500.11820/0b44579c-35ad-42b2-9be0-1da11c19f3c3 . 54951252 .
  4. 10.1039/c1sm06083j . On measuring colloidal volume fractions . 2012 . Poon . Wilson C. K. . Weeks . Eric R. . Royall . C. Patrick . Soft Matter . 8 . 1 . 21–30 . 1106.2566 . 2012SMat....8...21P . 23455559 .
  5. 10.1038/nature22813 . Selective sp3 C–H alkylation via polarity-match-based cross-coupling . 2017 . Le . Chip . Liang . Yufan . Evans . Ryan W. . Li . Ximing . MacMillan . David W. C. . Nature . 547 . 7661 . 79–83 . 28636596 . 5655994 . 2017Natur.547...79L .
  6. Evelyn M. . Hancock. Arthur C.. Cope. 10.15227/orgsyn.025.0025 . A-Cyclohexylphenylacetonitrile . Organic Syntheses . 1945 . 25 . 25 .

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