View source for Chlorobenzene

{{chembox
| verifiedrevid = 322111644
|   Name = Chlorobenzene
|   ImageFileL1 = Chlorobenzene2.svg
|   ImageSizeL1 = 85px
|   ImageNamL1e = Chlorobenzene
|   ImageFileR1 = Chlorobenzene-3D-vdW.png
|   ImageSizeR1 = 120px
|   ImageNameR1 = Chlorobenzene
|   IUPACName = chlorobenzene
|   OtherNames = benzene chloride<br />monochlorobenzene<br />Phenyl chloride
|   Abbreviations = PhCl
| Section1 = {{Chembox Identifiers
|   SMILES = Clc1ccccc1
|   ChemSpiderID = 7676
| PubChem = 7964
| InChI = 1/C6H5Cl/c7-6-4-2-1-3-5-6/h1-5H
| InChIKey = MVPPADPHJFYWMZ-UHFFFAOYAG
| CASNo_Ref = {{cascite}}
| CASNo = 108-90-7
|   RTECS = CZ0175000
  }}
| Section2 = {{Chembox Properties
|   Formula = C<sub>6</sub>H<sub>5</sub>Cl
|   MolarMass = 112.56 g/mol
|   Appearance = colorless liquid
|   Density = 1.11 g/cm³, liquid
|   Solubility = low
|   Solvent = other solvents
|   SolubleOther = soluble in most organic solvents
|   MeltingPtC = -45
|   BoilingPtC = 131
|   Viscosity = 
  }}

| Section7 = {{Chembox Hazards
|   NFPA-H = 3
|   NFPA-F = 3
|   NFPA-R = 0
|   ExternalMSDS =
|   MainHazards = 
|   FlashPt = 29 °C
|   RPhrases = {{R10}} {{R20}} {{R51/53}}
|   SPhrases = {{S24/25}} {{S61}}
  }}
| Section8 = {{Chembox Related
|   OtherFunctn = [[Fluorobenzene]]<br>[[Bromobenzene]]<br>[[Iodobenzene]]
|     Function = Halobenzenes
|   OtherCpds = [[benzene]]<br />[[1,4-Dichlorobenzene|1,4-dichlorobenzene]]
  }}
}}

'''Chlorobenzene''' is an [[aromatic]] [[organic compound]] with the chemical formula C<sub>6</sub>H<sub>5</sub>Cl. This colorless, flammable liquid  is a common solvent and a widely used intermediate in the manufacture of other chemicals.

==Uses==
Chlorobenzene once was used in the manufacture of certain [[pesticide]]s, most notably [[DDT]] by reaction with [[chloral]] (trichloroacetaldehyde), but this application has declined with the diminished use of DDT.  At one time, chlorobenzene was the main precursor for the manufacture of [[phenol]]:<ref>Manfred Weber, Markus Weber, Michael Kleine-Boymann, “Phenol” in Ullmann’s Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2005. {{DOI|10.1002/14356007.a19 299.pub2}}</ref>
:C<sub>6</sub>H<sub>5</sub>Cl  +  NaOH  →   C<sub>6</sub>H<sub>5</sub>OH  +  NaCl
The major use of chlorobenzene is as an intermediate in the production of commodities such as herbicides, dyestuffs, and rubber. Chlorobenzene is also used as a high-boiling [[solvent]] in many industrial applications as well as in the laboratory.<ref name=Ullmann>Manfred Rossberg et al. “Chlorinated Hydrocarbons” in Ullmann’s Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2006. {{DOI|10.1002/14356007.a06 233.pub2}}</ref>  Chlorobenzene is [[nitration|nitrated]] on a large scale to give a mixture of 2- and 4-nitrochlorobenzenes, which can be separated by [[fractional crystallization (chemistry)|fractional crystallization]] followed by distillation.  2-Nitrochlorobenzene (CAS#88-73-3) is converted to related 2-nitrophenol, 2-nitroanisole, bis(2-nitrophenyl)disulfide, and 2-nitropaniline by nucleophilic displacement of the chloride with [[sodium hydroxide]], [[sodium methoxide]], sodium disulfide and [[ammonia]].  The conversion of the [[4-nitrochlorobenzene]] (CAS#100-00-5) are similar.<ref name=Booth>Gerald Booth (2007). "Nitro Compounds, Aromatic". In: ''Ullmann's Encyclopedia of Industrial Chemistry''. John Wiley & Sons: New York. {{DOI|10.1002/14356007.a17_411}}</ref>

==Synthesis==
Chlorobenzene was first described in 1851.  Presently it is manufactured by [[Electrophilic halogenation|chlorination]] of [[benzene]] in the presence of a catalytic amount of [[Lewis acid]] such as [[ferric chloride]] and anhydrous aluminium chloride:
:[[Image:Chlorination benzene.svg|287px]]
The catalyst enhances the electrophilicity of the chlorine.  Because chlorine is electronegative, C<sub>6</sub>H<sub>5</sub>Cl exhibits decreased susceptibility to attack by other electrophiles. For this reason, the chlorination process produces only small amounts of dichloro- and trichlorobenzenes.

==Safety==
Chlorobenzene exhibits "low to moderate" toxicity as indicated by its [[LD50]] of 2.9 g/kg.<ref name=Ullmann/>

==References==
<references/>

[[Category:Aromatic compounds]]
[[Category:Halogenated solvents]]
[[Category:Organochlorides]]
[[Category:Hazardous air pollutants]]

[[cs:Chlorbenzen]]
[[de:Chlorbenzol]]
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[[ro:Clorura de benzol]]
[[ru:Хлорбензол]]
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