:Bromocyclohexane
{{Chembox
| Watchedfields = changed
| verifiedrevid = 455071282
| ImageFile = Cyclohexyl bromide.svg
| ImageSize = 80px
| PIN =Bromocyclohexane
| OtherNames = Cyclohexyl bromide
|Section1={{Chembox Identifiers
| InChI = 1/C6H11Br/c7-6-4-2-1-3-5-6/h6H,1-5H2
| InChIKey = AQNQQHJNRPDOQV-UHFFFAOYAD
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C6H11Br/c7-6-4-2-1-3-5-6/h6H,1-5H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = AQNQQHJNRPDOQV-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 108-85-0
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = YA0UMS4RNY
| PubChem = 7960
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7672
| SMILES =BrC1CCCCC1
| MeSHName =
}}
|Section2={{Chembox Properties
| Formula =C6H11Br
| MolarMass =163.06 g/mol
| Appearance =colorless liquid
| Density = 1.324 g/cm3
| MeltingPtC = -57
| BoilingPtC = 166 to 167
| BoilingPt_notes =
}}
|Section3={{Chembox Hazards
| FlashPtC = 62.8
}}
|Section6={{Chembox Related
| OtherCompounds = Chlorocyclohexane
Fluorocyclohexane
Iodocyclohexane
}}
}}
Bromocyclohexane (also called cyclohexyl bromide, abbreviated CXB) is an organic compound with the chemical formula {{chem2|(CH2)5CHBr}}.
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.{{cite journal | doi = 10.1007/s00348-010-0996-8 | title = Refractive-index and density matching in concentrated particle suspensions: A review | year = 2011 | last1 = Wiederseiner | first1 = Sébastien | last2 = Andreini | first2 = Nicolas | last3 = Epely-Chauvin | first3 = Gaël | last4 = Ancey | first4 = Christophe | journal = Experiments in Fluids | volume = 50 | issue = 5 | pages = 1183–1206 | bibcode = 2011ExFl...50.1183W | s2cid = 33720382 | url = https://infoscience.epfl.ch/record/162753/files/348_2010_Article_996.pdf }} Due to the moderate dielectric constant of CXB (ε = 7.9 {{Cite web |url=http://www.deltacnt.com/99-00032.htm |title=Dielectric Constants of Various Materials |access-date=2013-10-30 |archive-url=https://web.archive.org/web/20131101180301/http://www.deltacnt.com/99-00032.htm |archive-date=2013-11-01 |url-status=dead }}), 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.{{cite journal | doi = 10.1039/c2sm26245b | title = In search of colloidal hard spheres | year = 2013 | last1 = Royall | first1 = C. Patrick | last2 = Poon | first2 = Wilson C. K. | last3 = Weeks | first3 = Eric R. | journal = Soft Matter | volume = 9 | issue = 1 | pages = 17–27 | arxiv = 1205.6665 | bibcode = 2013SMat....9...17R | hdl = 20.500.11820/0b44579c-35ad-42b2-9be0-1da11c19f3c3 | s2cid = 54951252 | url = https://www.research.ed.ac.uk/en/publications/0b44579c-35ad-42b2-9be0-1da11c19f3c3 }} 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.{{cite journal | doi = 10.1039/c1sm06083j | title = On measuring colloidal volume fractions | year = 2012 | last1 = Poon | first1 = Wilson C. K. | last2 = Weeks | first2 = Eric R. | last3 = Royall | first3 = C. Patrick | journal = Soft Matter | volume = 8 | issue = 1 | pages = 21–30 | arxiv = 1106.2566 | bibcode = 2012SMat....8...21P | s2cid = 23455559 }}
It is a standard coupling partner of cross coupling reactions.{{cite journal |doi=10.1038/nature22813 |title=Selective sp3 C–H alkylation via polarity-match-based cross-coupling |year=2017 |last1=Le |first1=Chip |last2=Liang |first2=Yufan |last3=Evans |first3=Ryan W. |last4=Li |first4=Ximing |last5=MacMillan |first5=David W. C. |journal=Nature |volume=547 |issue=7661 |pages=79–83 |pmid=28636596 |pmc=5655994 |bibcode=2017Natur.547...79L }} Similarly, cyclohexyl bromide is a standard alkylating agent.{{cite journal |first1=Evelyn M. |last1=Hancock|first2= Arthur C.|last2= Cope|doi=10.15227/orgsyn.025.0025 |title=A-Cyclohexylphenylacetonitrile |journal=Organic Syntheses |year=1945 |volume=25 |page=25 }}
Synthesis
Bromocyclohexane can be prepared by the free radical bromination of cyclohexane.
Safety
Bromocyclohexane is an alkylating agent.
References
{{reflist}}
{{Bromine compounds}}