Benzoic anhydride

Short description: Chemical compound (C6H5CO)2O

Benzoic anhydride[1]

Names
Preferred IUPAC name

Benzoic anhydride

Other names

Benzoic acid anhydride
Benzoyl anhydride
Benzoyl benzoate

Identifiers

CAS Number

* 93-97-0 Y

3D model (JSmol)

* Interactive image

Abbreviations  | Bz2O

Beilstein Reference

| 516726
ChemSpider |

* 6899 Y

EC Number |

* 202-291-1

PubChem CID

* 7167

UNII |

* 9K7X34FOV2 Y

InChI

* InChI=1S/C14H10O3/c15-13(11-7-3-1-4-8-11)17-14(16)12-9-5-2-6-10-12/h1-10H Y

Key: CHIHQLCVLOXUJW-UHFFFAOYSA-N Y

SMILES

* c1ccccc1C(=O)OC(=O)c2ccccc2

Properties

Chemical formula

| C14H10O3
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)  |

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

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. Benzoic anhydride provides a convenient way to prepare benzoic esters:

(C6H5CO)2O + ROH → C6H5CO2H + C6H5CO2R

## References

1. ↑ "Sciencelab msds". http://www.sciencelab.com/msds.php?msdsId=9923052.
2. ↑ "aldrich product page". http://www.sigmaaldrich.com/catalog/product/aldrich/385980?lang=hu&region=HU.
3. ↑ H. T. Clarke; E. J. Rahrs (1923). "Benzoic Anhydride". Org. Synth. 3: 21. doi:10.15227/orgsyn.003.0021.

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*[CID]: Compound ID