Updating {{chembox}} (changes to watched fields - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:WikiProject_Chemi |
Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: StdInChI StdInChIKey. |
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| InChIKey = PASDCCFISLVPSO-UHFFFAOYAL |
| InChIKey = PASDCCFISLVPSO-UHFFFAOYAL |
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| SMILES1 = c1ccc(cc1)C(=O)Cl |
| SMILES1 = c1ccc(cc1)C(=O)Cl |
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| StdInChI = 1S/C7H5ClO/c8-7(9)6-4-2-1-3-5-6/h1-5H |
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| StdInChIKey = PASDCCFISLVPSO-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 98-88-4 |
| CASNo = 98-88-4 |
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Revision as of 16:26, 29 November 2010
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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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| ChemSpider | |||
| ECHA InfoCard | 100.002.464 | ||
PubChem CID
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| 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 (30 °F; 272 K) | ||
| Boiling point | 197.2 °C (387.0 °F; 470.3 K) | ||
| 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 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 production 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 benzoic acid with chlorine.[2]
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:
- C6H5COCl + H2O → C6H5CO2H + HCl
Benzoyl chloride reacts with sodium peroxide to give benzoyl peroxide and sodium chloride:[citation needed]
- 2 C6H5COCl + Na2O2 → (C6H5CO)2O2 + 2 NaCl
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
- ^ Friedrich Wöhler, Justus von Liebig (1832). "Untersuchungen über das Radikal der Benzoesäure". Annalen der Pharmacie. 3: 249–282. doi:10.1002/jlac.18320030302.