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Revision as of 22:52, 6 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEBI_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:WikiProject_Chem← Previous edit		Latest revision as of 20:33, 23 February 2024 edit undoTGSpecialist1 (talk | contribs)58 editsm →See also
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			{{Distinguish|Bromotoluene}}
	{{chembox		{{chembox
			| Verifiedfields = changed
⚫	| verifiedrevid = 443418196
			| Watchedfields = changed
	| Reference=<ref>'']'', 11th Edition, '''1142'''</ref>
		⚫	| verifiedrevid = 443419516
⚫	| Name = Benzyl bromide
			| Reference = <ref>{{cite book|title=Merck Index |edition=11th |page=1142|title-link=Merck Index }}</ref>
	| ImageFileL1 = Benzyl-bromide-skeletal.svg
		⚫	| Name = Benzyl bromide
	| ImageSizeL1 = 120px
	| ImageNameL1 = Skeletal structure of the benzyl bromide molecule		| ImageFileL1 = Benzyl bromide.svg
			| ImageNameL1 = Skeletal structure of the benzyl bromide molecule
	| ImageFileR1 = Benzyl-bromide-3D-vdW.png		| ImageFileR1 = Benzyl-bromide-from-clathrate-xtal-3D-sf.png
		⚫	| ImageNameR1 = 3D structure of the benzyl bromide molecule
	| ImageSizeR1 = 100px
			| PIN = (Bromomethyl)benzene <!-- Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) -->
⚫	| ImageNameR1 = 3D structure of the benzyl bromide molecule
			| SystematicName =
⚫	| IUPACName = Bromomethylbenzene
			| OtherNames = α-Bromotoluene<br />Benzyl bromide
		⚫	| IUPACName =
	| Section1 = {{Chembox Identifiers		| Section1 = {{Chembox Identifiers
			| IUPHAR_ligand = 6294
	| InChI = 1/C7H7Br/c8-6-7-4-2-1-3-5-7/h1-5H,6H2		| InChI = 1/C7H7Br/c8-6-7-4-2-1-3-5-7/h1-5H,6H2
	| InChIKey = AGEZXYOZHKGVCM-UHFFFAOYAM		| InChIKey = AGEZXYOZHKGVCM-UHFFFAOYAM
	| SMILES1 = c1ccc(cc1)CBr		| SMILES1 = c1ccc(cc1)CBr
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	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 100-39-0		| CASNo = 100-39-0
			| UNII_Ref = {{fdacite|changed|FDA}}
⚫	| PubChem = 7498
			| UNII = XR75BS721D
⚫	| ChEBI_Ref = {{ebicite|correct|EBI}}
		⚫	| PubChem = 7498
		⚫	| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 59858		| ChEBI = 59858
	| SMILES = BrCc1ccccc1		| SMILES = BrCc1ccccc1
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	}}		}}
	| Section2 = {{Chembox Properties		| Section2 = {{Chembox Properties
			| C=7 | H=7 | Br=1
	| Formula = C<sub>7</sub>H<sub>7</sub>Br
			| Appearance = Colorless liquid
	| MolarMass = 171.04 g/mol
			| Odor = Sharp and pungent
	| Density = 1.438 g/cm³ at 20&nbsp;°C		| Density = 1.438 g/cm<sup>3</sup>
	| MeltingPtC = -3.9		| MeltingPtC = -3.9
	| BoilingPt = 198-199&nbsp;°C
			| BoilingPtC = 201
			| SolubleOther = organic solvents
			| RefractIndex = 1.5752
			| LogP = 2.92<ref name="chemsrc">{{Cite web|url=https://www.chemsrc.com/en/cas/100-39-0_401904.html|title=Benzyl bromide_msds}}</ref>
			}}
			| Section3 =
			| Section4 =
			| Section5 =
			| Section6 =
			| Section7 = {{Chembox Hazards
			| FlashPtC = 70
			| GHSPictograms = {{GHS07}}
	}}		}}
	}}		}}
			'''Benzyl bromide''' is an ] with the formula {{chem2|C6H5CH2Br}}. The molecule consists of a ] ring substituted with a bromomethyl group. It is a colorless liquid with lachrymatory properties. The compound is a reagent for introducing ]s.<ref name=eEROS>{{cite journal|title=Benzyl Bromide|author=William E. Bauta|journal=Encyclopedia of Reagents for Organic Synthesis|year=2001|doi=10.1002/047084289X.rb047|isbn=0-471-93623-5}}</ref><ref>{{cite web|title=Benzyl bromide|url=http://www.sigmaaldrich.com/catalog/product/aldrich/b17905?lang=en&region=RU|website=]|publisher=sigmaaldrich.com|access-date=8 June 2017}}</ref>
	'''Benzyl bromide''', or α-bromotoluene, is an ] consisting of a ] ring substituted with a bromomethyl group. It can be prepared by the bromination of ] at room temperature in air, using ] as a heterogeneous catalyst. It is a colorless liquid that is decomposed slowly in water.
			== Synthesis and structure==
	Benzyl bromide is used in ] for the introduction of the benzyl ] for ]s and ]s.
		⚫	Benzyl bromide can be synthesized by the bromination of ] under conditions suitable for a ]:
		⚫	:]
			The structure has been examined by electron diffraction.<ref>{{cite journal|last1=Vilkov|first1=L. V.|last2=Sadova|first2=N. I.|title=Electron diffraction study on the molecular structure of benzyl chloride and benzyl bromide in the vapour phase|journal=]|date=March 1976|volume=31|issue=1|pages=131–142|doi=10.1016/0022-2860(76)80124-X|bibcode=1976JMoSt..31..131S }}</ref>
⚫	Benzyl bromide is a strong ] and is also intensely irritating to skin and mucous membranes. Because of these properties, it has been used as a war gas.
	== Synthesis ==		==Applications==
			Benzyl bromide is used in ] for the introduction of the benzyl groups when the less expensive ] is insufficiently reactive.<ref>{{cite journal|title=Synthesis and Diastereoselective Alkylation of Pseudoephenedrine Amides |author=Andrew G. Myers |author2=Bryant H. Yang|journal=Org. Synth.|year=2000|volume=77|page=22|doi=10.15227/orgsyn.077.0022}}</ref>
⚫	Benzyl bromide can be synthesized by the bromination of ] under conditions suitable for a ]:
			<ref>{{cite journal|title=1-Benzylindole |author=Harry Heaney |author2=Steven V. Ley|journal=Org. Synth.|year=1974|volume=54|page=58|doi=10.15227/orgsyn.054.0058}}</ref> Benzylations are often achieved in the presence of catalytic amounts of ], which generates the more reactive benzyl iodide in situ.<ref name=eEROS/> In some cases, benzyl serves as ] for ]s and ]s.<ref>{{cite web|title=Benzyl bromide|url=http://www.chemicalbook.com/ChemicalProductProperty_EN_CB6761035.htm|publisher=chemicalbook.com|access-date=8 June 2017}}</ref>
			==Safety==
⚫	]
		⚫	Benzyl bromide is a strong ] and is also intensely irritating to skin and mucous membranes. Because of these properties, it has been used in ], both in combat and in training due to its irritating yet non-lethal nature.
	] may also be used in place of elemental bromine.
	== See also ==		== See also ==
	* ]		* ]
			* ]
			* ]
			* ]
	== References ==		== References ==
	{{reflist}}		{{reflist}}
			{{Chemical agents}}
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