Benzoyl chloride

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
C=7|H=5|Cl=1|O=1
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, C₆H₅COCl, with an irritating odour. In the laboratory it may be prepared by distilling benzoic acid (C₆H₅COOH) 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 dyes, perfumes, peroxides, pharmaceuticals, and resins. It is also used in photography; as gasoline gum inhibitors, and in the manufacture of synthetic tannins. It was formerly employed as an irritant gas in chemical warfare.

Reactions

Like all other acyl chlorides, benzoyl chloride can also react with alcohols and amines to give the corresponding esters and amides.

Benzoyl chloride is easily hydrolyzed; it reacts with water to produce hydrochloric acid and benzoic acid.

: PhCOCl + H₂O → PhCOOH + HCl

External links

* [http://www.ilo.org/public/english/protection/safework/cis/products/icsc/dtasht/_icsc10/icsc1015.htm International Chemical Safety Card 1015]