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 &deg;C | BoilingPt = 197.2 &deg;C | Solubility = reacts }} | Section3 = {{Chembox Hazards | MainHazards = Corrosive ('''C''') | FlashPt = 72 &deg;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 &rarr; 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]]