Benzoyl chloride
1671767
188758101
2008-02-03T07:18:48Z
Puppy8800
5404759
{{Chembox new
| ImageFile = Benzoyl chloride.svg
| ImageFileL1 = Benzoyl-chloride-3D-balls.png
| ImageFileR1 = Benzoyl-chloride-3D-vdW.png
| IUPACName = Benzoyl chloride
| Section1 = {{Chembox Identifiers
| CASNo = 98-88-4
| PubChem =
| SMILES = ClC(=O)c1ccccc1
| RTECS = DM6600000
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>7</sub>H<sub>5</sub>ClO
| MolarMass = 140.567 g/mol
| Appearance = colorless liquid
| Density = 1.21 g/mL, liquid
| MeltingPt = -1 °C
| BoilingPt = 197.2 °C
| Solubility = reacts
}}
| Section3 = {{Chembox Hazards
| MainHazards = Corrosive ('''C''')
| FlashPt = 72 °C
| Autoignition =
| RPhrases = {{R34}}
| SPhrases = {{(S1/2)}} {{S26}} {{S45}}
}}
| Section8 = {{Chembox Related
| Function = [[acyl chloride]]
| OtherCpds = [[benzoic acid]], [[benzoic anhydride]], [[benzaldehyde]]}}
}}
'''Benzoyl chloride''', also known as benzenecarbonyl chloride, is a colourless, fuming liquid, C<sub>6</sub>H<sub>5</sub>COCl, with an irritating odour. In the laboratory it may be prepared by distilling [[benzoic acid]] (C<sub>6</sub>H<sub>5</sub>COOH) with [[phosphorus pentachloride]] in [[anhydrous]] conditions. This replaces the hydroxyl group of benzoic acid with a chlorine atom. This chlorination can also be accomplished using [[thionyl chloride]]. On a larger scale it is prepared by chlorinating [[benzaldehyde]].
This substance is used as an intermediate chemical in the preparation of [[dye]]s, [[perfume]]s, [[organic peroxide|peroxide]]s, [[pharmaceutical]]s, and [[resin]]s. It is also used in [[photography]]; as gasoline gum inhibitors, and in the manufacture of synthetic [[tannin]]s. It was formerly employed as an irritant gas in [[chemical warfare]].
==Reactions==
Like all other [[acyl chloride]]s, benzoyl chloride can also react with [[alcohol]]s and [[amine]]s to give the corresponding [[ester]]s and [[amide]]s.
Benzoyl chloride is easily hydrolyzed; it reacts with water to produce [[hydrochloric acid]] and [[benzoic acid]].
: PhCOCl + H<sub>2</sub>O → PhCOOH + HCl
== External links ==
* [http://www.ilo.org/public/english/protection/safework/cis/products/icsc/dtasht/_icsc10/icsc1015.htm International Chemical Safety Card 1015]
[[Category:Acyl chlorides]]
[[Category:Aromatic compounds]]
[[de:Benzoylchlorid]]
[[ja:塩化ベンゾイル]]
[[pl:Chlorek benzoilu]]
[[pt:Cloreto de benzoíla]]
[[zh:苯甲酰氯]]