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Revision as of 17:40, 11 October 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:WikiProject_Chemicals|er...← Previous edit Latest revision as of 19:42, 31 July 2024 edit undoJWBE (talk | contribs)Extended confirmed users10,126 edits removed Category:Cyclohexanes; added Category:Cyclohexyl compounds using HotCat 
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{{Chembox {{Chembox
| Watchedfields = changed
| verifiedrevid = 432092795 | verifiedrevid = 455071282
| ImageFile = Cyclohexyl bromide.svg | ImageFile = Cyclohexyl bromide.svg
| ImageSize = 80px | ImageSize = 80px
| PIN =Bromocyclohexane
|IUPACName=bromocyclohexane
| OtherNames = cyclohexyl bromide | OtherNames = Cyclohexyl bromide
|Section1= {{Chembox Identifiers |Section1={{Chembox Identifiers
| InChI = 1/C6H11Br/c7-6-4-2-1-3-5-6/h6H,1-5H2 | InChI = 1/C6H11Br/c7-6-4-2-1-3-5-6/h6H,1-5H2
| InChIKey = AQNQQHJNRPDOQV-UHFFFAOYAD | InChIKey = AQNQQHJNRPDOQV-UHFFFAOYAD
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| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 108-85-0 | CASNo = 108-85-0
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = YA0UMS4RNY
| PubChem = 7960 | PubChem = 7960
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7672 | ChemSpiderID = 7672
| SMILES=BrC1CCCCC1 | SMILES =BrC1CCCCC1
| MeSHName= | MeSHName =
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| Formula=C<sub>6</sub>H<sub>11</sub>Br | Formula =C<sub>6</sub>H<sub>11</sub>Br
| MolarMass =163.06 | MolarMass =163.06 g/mol
| Appearance=colorless liquid | Appearance =colorless liquid
| Density= 1.324 g/cm<sup>3</sup> | Density = 1.324 g/cm<sup>3</sup>
| MeltingPtC = -57
| MeltingPt =
| BoilingPt =166-167 °C | BoilingPtC = 166 to 167
| BoilingPt_notes =
}} }}
|Section3= {{Chembox Hazards |Section3={{Chembox Hazards
| FlashPt=62.8 °C | FlashPtC = 62.8
}} }}
|Section6={{Chembox Related
| OtherCompounds = ]<br>]<br>]
}}
}} }}


'''Bromocyclohexane''' is an organic ] with the ] C<sub>6</sub>H<sub>11</sub>Br. '''Bromocyclohexane''' (also called '''cyclohexyl bromide''', abbreviated '''CXB''') is an organic ] with the ] {{chem2|(CH2)5CHBr}}.


==Uses and reactions==
It is used to match the ] of ] for example in ] of ]. A mixture of ''cis''-] and CXB can simultaneously match optical index and density of PMMA.<ref>{{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 }}</ref> Due to the moderate ] of CXB (ε = 7.9 <ref>{{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 }}</ref>), PMMA acquires charges that can be screened by the addition of salt (e.g. ]), leading to a very good approximation of colloidal ].<ref>{{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 }}</ref> 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.<ref>{{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 }}</ref>


It is a standard ] of ]s.<ref>{{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 }}</ref> Similarly, cyclohexyl bromide is a standard ].<ref>{{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 }}</ref>
{{organohalide-stub}}


== Synthesis ==
⚫ ]
Bromocyclohexane can be prepared by the free radical bromination of ].


==Safety==
]
Bromocyclohexane is an ].
]

== References ==
{{reflist}}

{{Bromine compounds}}

⚫ ]
]
]