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.