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Benzoyl chloride



Benzoyl chloride
IUPAC name Benzoyl chloride
Identifiers
CAS number 98-88-4
RTECS number DM6600000
SMILES ClC(=O)c1ccccc1
Properties
Molecular formula C7H5ClO
Molar mass 140.567 g/mol
Appearance colorless liquid
Density 1.21 g/mL, liquid
Melting point

-1 °C

Boiling point

197.2 °C

Solubility in water reacts
Hazards
Main hazards Corrosive (C)
R-phrases R34
S-phrases (S1/2) S26 S45
Flash point 72 °C
Related Compounds
Related compounds benzoic acid, benzoic anhydride, benzaldehyde
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

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.

Additional recommended knowledge

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, just as any acyl chloride can.

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

PhCOCl + H2O → PhCOOH + HCl
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Benzoyl_chloride". A list of authors is available in Wikipedia.
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