Benzoic anhydride
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Preferred IUPAC name Benzoic anhydride | |
Other names Benzoic acid anhydride Benzoyl anhydride Benzoyl benzoate | |
Identifiers | |
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3D model (JSmol) |
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Beilstein Reference | 516726 |
ChemSpider |
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ECHA InfoCard | 100.002.084 |
EC Number |
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PubChem CID |
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UNII |
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CompTox Dashboard (EPA) |
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InChI
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Properties | |
Chemical formula | C 14H 10O 3 |
Molar mass | 226.23 g mol−1 |
Appearance | White to off-white solid |
Density | 1.1989 g cm−3 at 15 °C |
Melting point | 42 °C (108 °F; 315 K) |
Boiling point | 360 °C (680 °F; 633 K) |
Magnetic susceptibility (χ) | -124.9·10−6 cm3/mol |
Hazards | |
NFPA 704 (fire diamond) | 1 2 1 |
Flash point | 113[2] °C (235 °F; 386 K) |
Related compounds | |
Related compounds | Benzoic acid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references |
Chemical compound
Benzoic anhydride is the organic compound with the formula (C6H5CO)2O. It is the acid anhydride of benzoic acid and the simplest symmetrical aromatic acid anhydride. It is a white solid.
Preparation and reactions
It is usually prepared by the dehydration reaction of benzoic acid, e.g. using acetic anhydride:[3]
- 2 C6H5CO2H + (CH3CO)2O → (C6H5CO)2O + 2 CH3CO2H
Alternatively, sodium benzoate can be treated with benzoyl chloride. It can be produced by dehydrating benzoic acid by heating. [citation needed]
Benzoic anhydride provides a convenient way to prepare benzoic esters:
- (C6H5CO)2O + ROH → C6H5CO2H + C6H5CO2R