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]]