Benzoic_anhydride
Benzoic anhydride
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.
Quick Facts Names, Identifiers ...
Names | |
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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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516726 | |
ChemSpider |
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ECHA InfoCard | 100.002.084 |
EC Number |
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PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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Properties | |
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) |
-124.9·10−6 cm3/mol | |
Hazards | |
NFPA 704 (fire diamond) | |
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).
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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
- "Sciencelab msds". Archived from the original on 2016-03-04. Retrieved 2015-12-26.
- H. T. Clarke; E. J. Rahrs (1923). "Benzoic Anhydride". Org. Synth. 3: 21. doi:10.15227/orgsyn.003.0021.