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
CAS Number	108-85-0 Y
3D model (JSmol)	Interactive image
ChemSpider	7672 Y
ECHA InfoCard	100.003.294
PubChem CID	7960
UNII	YA0UMS4RNY Y
CompTox Dashboard (EPA)	DTXSID1044148
InChI InChI=1S/C6H11Br/c7-6-4-2-1-3-5-6/h6H,1-5H2 Y Key: AQNQQHJNRPDOQV-UHFFFAOYSA-N Y InChI=1/C6H11Br/c7-6-4-2-1-3-5-6/h6H,1-5H2 Key: AQNQQHJNRPDOQV-UHFFFAOYAD
SMILES BrC1CCCCC1
Properties
Chemical formula	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). Y verify (what is YN ?) 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.