Benzoyl chloride
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| Benzoyl Chloride | |||
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| Names | |||
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| IUPAC name
Benzoyl Chloride
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| Identifiers | |||
98-88-4  |
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| ChemSpider | 7134 |
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| Jmol 3D model | Interactive image Interactive image |
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| KEGG | C19168 |
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| PubChem | 7412 | ||
| RTECS number | DM6600000 | ||
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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 (30 °F; 272 K) | ||
| Boiling point | 197.2 °C (387.0 °F; 470.3 K) | ||
| reacts | |||
| Vapor pressure | {{{value}}} | ||
| Related compounds | |||
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Related compounds
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benzoic acid, benzoic anhydride, benzaldehyde | ||
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |||
Benzoyl chloride, also known as benzenecarbonyl chloride, is an organochlorine compound with the formula C6H5COCl. It is a colourless, fuming liquid with an irritating odour. It is mainly useful for the production of peroxides but is generally useful in other areas such as in the preparation of dyes, perfumes, pharmaceuticals, and resins.
Preparation
Benzoyl chloride is produced from benzotrichloride using either water or benzoic acid:[1]
- C6H5CCl3 + H2O → C6H5COCl + 2 HCl
- C6H5CCl3 + C6H5CO2H → 2 C6H5COCl + HCl
As for other acyl chlorides, it can be generated from the parent acid and other chlorinating agents phosphorus pentachloride or thionyl chloride. It was first prepared by treatment of benzaldehyde with chlorine.[2]
An early method for production of benzoyl chloride involved chlorination of benzyl alcohol.[3]
Reactions
It reacts with water to produce hydrochloric acid and benzoic acid:
- C6H5COCl + H2O → C6H5CO2H + HCl
Benzoyl chloride is a typical acyl chloride. It reacts with alcohols to give the corresponding esters. Similarly, it reacts with amines to give the amide.[4][5]
It undergoes the Friedel-Crafts acylation with aromatic compoundss to give the corresponding benzophenones and related derivatives.[6] With carbanions, it serves again as a source of "PhCO+".[7]
Benzoyl peroxide, a common reagent in polymer chemistry, is produced industrially by treating benzoyl chloride with hydrogen peroxide and sodium hydroxide:[8]
- 2 C6H5COCl + H2O2 + 2 NaOH → (C6H5CO)2O2 + 2 NaCl + 2 H2O
References
- ↑ Takao Maki, Kazuo Takeda “Benzoic Acid and Derivatives” Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi: 10.1002/14356007.a03_555
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ US1851832, 29 March 1932
- ↑ C. S. Marvel And W. A. Lazier "Benzoyl Piperidine" Org. Synth. 1929, volume 9, pp. 16. doi:10.15227/orgsyn.009.0016
- ↑ Prasenjit Saha, Md Ashif Ali, and Tharmalingam Punniyamurthy "Ligand-free Copper(ii) Oxide Nanoparticles Catalyzed Synthesis Of Substituted Benzoxazoles" Org. Synth. 2011, volume 88, pp. 398. doi:10.15227/orgsyn.088.0398. (an illustrative reaction of an amine with benzoyl chloride).
- ↑ Wesley Minnis "Phenyl Thienyl Ketone" Org. Synth. 1932, vol. 12, pp. 62. doi:10.15227/orgsyn.012.0062
- ↑ M. Fujita and T. Hiyama "Directed Reduction of a beta-keto Amide: Erythro-1-(3-hydroxy-2-methyl-3-phenylpropanoyl)piperidine" Org. Synth. 1990, volume 69, pp. 44. doi:10.15227/orgsyn.069.0044
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
