Benzoyl chloride
From Wikipedia, the free encyclopedia
| Benzoyl chloride | |
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| 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 |
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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.
[edit] 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
