Chlorobenzene
2029608
220347956
2008-06-19T12:32:59Z
Smokefoot
698909
Info on synthesis (rm original research on Cl2---Fe bonding) and uses (including rxn with NaOH to give PhOH)
{{Chembox new
| Name = Chlorobenzene
| ImageFileL1 = Chlorobenzene-2D-skeletal.png
| ImageSizeL1 = 80px
| ImageNamL1e = Chlorobenzene
| ImageFileR1 = Chlorobenzene-3D-vdW.png
| ImageSizeR1 = 100px
| ImageNameR1 = Chlorobenzene
| IUPACName = chlorobenzene
| OtherNames = benzene chloride<br />monochlorobenzene<br />Phenyl chloride
| Section1 = {{Chembox Identifiers
| SMILES = ClC1=CC=CC=C1
| 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 = most organic solvents
| MeltingPt = -45 °C (228 K)
| BoilingPt = 131 °C (404 K)
| Viscosity =
}}
| Section7 = {{Chembox Hazards
| ExternalMSDS =
| MainHazards =
| FlashPt = 29 °C
| RPhrases = 10 20 51/53
| SPhrases = 24/25 61
}}
| Section8 = {{Chembox Related
| 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 a 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
As of 2005, 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. More specifically, the chlorobenzene is nitrated on a large scale to give nitrochlorobenene, which is converted to related phenol, anisole, and aniline derivatives.<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>
==Synthesis==
Chlorobenzene was first described in [[1851]], when it was prepared by reacting [[phenol]] and [[phosphorus pentachloride]].{{Fact|date=February 2007}} Presently it is manufactured by [[Electrophilic halogenation|chlorination]] of [[benzene]] in the presence of a catalytic amount of [[Lewis acid]] such as [[ferric chloride]]:
<center>[[Image:Chlorination_benzene.jpg]]</center>
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]]
[[de:Chlorbenzol]]
[[eo:Klorbenzolo]]
[[fr:Chlorobenzène]]
[[lv:Hlorbenzols]]
[[ja:クロロベンゼン]]
[[no:Klorbenzen]]
[[pl:Chlorobenzen]]
[[pt:Clorobenzeno]]
[[ro:Clorura de benzol]]
[[fi:Klooribentseeni]]
[[zh:氯苯]]