Benzoyl chloride
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| Names | |||
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| IUPAC name
Benzoyl chloride
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| Identifiers | |||
3D model (JSmol)
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| ECHA InfoCard | 100.002.464 | ||
| RTECS number |
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CompTox Dashboard (EPA)
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| Properties | |||
| C7H5ClO | |||
| Molar mass | 140.57 g·mol−1 | ||
| Appearance | colorless liquid | ||
| Density | 1.21 g/mL, liquid | ||
| Melting point | -1 °C | ||
| Boiling point | 197.2 °C | ||
| reacts | |||
| Hazards | |||
| Flash point | 72 °C | ||
| Related compounds | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Benzoyl chloride, also known as benzenecarbonyl chloride, is a colourless, fuming liquid, C6H5COCl, with an irritating odour.
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.
Preparation
Preparation of benzoyl chlorides is similar to that of other acyl chlorides: by reacting benzoic acid (C6H5COOH) with phosphorus pentachloride or thionyl chloride. Alternatively, it may be prepared by chlorinating benzaldehyde;[1] this is an industrial process.[citation needed]
Reactions
Benzoyl chloride is a typical acyl chloride. It reacts with alcohols and amines to give the corresponding esters and amides. It undergoes the Friedel-Crafts acylation with arenes to give the corresponding benzophenones. Similarly, it reacts with water to produce hydrochloric acid and benzoic acid:
- PhCOCl + H2O → PhCOOH + HCl
Benzoyl chloride reacts with sodium peroxide to give benzoyl peroxide and sodium chloride:[citation needed]
- 2 PhCOCl + Na2O2 → (PhCO)2O2 + 2 NaCl
References
- ^ Friedrich Wöhler; Justus von Liebig (1832). "Untersuchungen über das Radikal der Benzoesäure". Annalen der Pharmacie. 3: 249. doi:10.1002/jlac.18320030302.
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