View source for Benzotrichloride

{{chembox
| verifiedrevid = 322349094
|
| ImageFile = Benzotrichloride.png
| ImageSize = 120px
| IUPACName = (Trichloromethyl)benzene
| OtherNames = Toluene trichloride<br>Phenyl chloroform<br>alpha,alpha,alpha-Trichlorotoluene
| Section1 = {{Chembox Identifiers
| Abbreviations = 
| ChemSpiderID = 7089
| CASNo_Ref = {{cascite}}
| CASNo = 98-07-7
| EINECS = 
| PubChem = 
| SMILES = ClC(Cl)(Cl)C1=CC=CC=C1
| InChI = 
| RTECS = XT9275000 
| MeSHName =
| ChEBI =
| KEGG = 
| ATCCode_prefix = 
| ATCCode_suffix = 
| ATC_Supplemental =}}
| Section2 = {{Chembox Properties
| Formula = C<sub>7</sub>H<sub>5</sub>Cl<sub>3</sub>
| MolarMass = 195.48
| Appearance = Clear liquid
| Density = 1.3756 g/mL
| MeltingPt = -5.0 °C
| Melting_notes =
| BoilingPt = 220.8 °C
| Boiling_notes = 
| Solubility = 0.05g/L<!--From Ullmann-->
| SolubleOther = organic solvents
| Solvent = 
| pKa = 
| pKb = }}
| Section7 = {{Chembox Hazards
| EUClass = 
| EUIndex = 
| MainHazards = 
| NFPA-H = 3
| NFPA-F = 1
| NFPA-R = 0
| NFPA-O =
| RPhrases = {{R45}} {{R22}} {{R23}} {{R37/38}} {{R41}}
| SPhrases = {{S53}} {{S45}}
| RSPhrases =
| FlashPt = 
| Autoignition = 
| ExploLimits = 
| PEL = }}
}}

'''Benzotrichloride''', also known as trichlorotoluene is an [[organic compound]] with the [[chemical formula|formula]] C<sub>6</sub>H<sub>5</sub>CCl<sub>3</sub>.  It is principally used as an intermediate in the preparation of other chemical products such as dyes.<ref name="Merck">''Merck Index'', 11th Edition, '''1120'''.</ref><ref>[http://www.inchem.org/documents/icsc/icsc/eics0105.htm Benzotrichloride] Data page at Inchem.org</ref>

==Production and uses==
Benzotrichloride is produced by the [[free radical]] [[chlorination]] of [[toluene]], catalysed by light or [[radical initiator]]s such as [[dibenzoyl peroxide]].  Two intermediates are observed:
: C<sub>6</sub>H<sub>5</sub>CH<sub>3</sub>  +  Cl<sub>2</sub>   →  [[Benzyl chloride|C<sub>6</sub>H<sub>5</sub>CH<sub>2</sub>Cl]] +  HCl
: C<sub>6</sub>H<sub>5</sub>CH<sub>2</sub>Cl  +  Cl<sub>2</sub>   →  [[Benzal chloride|C<sub>6</sub>H<sub>5</sub>CHCl<sub>2</sub>]]  +  HCl
: C<sub>6</sub>H<sub>5</sub>CHCl<sub>2</sub>  +  Cl<sub>2</sub>   →  C<sub>6</sub>H<sub>5</sub>CCl<sub>3</sub>  +  HCl

Benzotrichloride is [[hydrolysis|hydrolysed]] to [[benzoyl chloride]]:<ref>Manfred Rossberg, Wilhelm Lendle, Gerhard Pfleiderer, Adolf Tögel, Eberhard-Ludwig Dreher, Ernst Langer, Heinz Rassaerts, Peter Kleinschmidt, Heinz Strack, Richard Cook, Uwe Beck, Karl-August Lipper, Theodore R. Torkelson, Eckhard Löser, Klaus K. Beutel, “Chlorinated Hydrocarbons” in Ullmann’s Encyclopedia of Chemical Technology, 2007 John Wiley & Sons: New York.</ref>
: C<sub>6</sub>H<sub>5</sub>CCl<sub>3</sub>  +  H<sub>2</sub>O   →  C<sub>6</sub>H<sub>5</sub>C(O)Cl  +  2 HCl
It is also transformed into [[benzotrifluoride]], a precursor to pesticides:
: C<sub>6</sub>H<sub>5</sub>CCl<sub>3</sub>  +  3 KF   →  C<sub>6</sub>H<sub>5</sub>CF<sub>3</sub>  +  3 KCl

==References==
<references/>

[[Category:Halogenated solvents]]
[[Category:Organochlorides]]
[[Category:Aromatic compounds]]
[[Category:IARC Group 2A carcinogens]]

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[[fr:(trichlorométhyl)benzène]]
[[nl:Trichloormethylbenzeen]]
[[Category:2Fix]]