Benzoic anhydride

Benzoic anhydride[1]
Names
	Preferred IUPAC name Benzoic anhydride
	Other names Benzoic acid anhydride; Benzoyl anhydride; Benzoyl benzoate
Identifiers
CAS Number	93-97-0 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	516726
ChemSpider	6899 ;
ECHA InfoCard	100.002.084
EC Number	202-291-1;
PubChem CID	7167;
UNII	9K7X34FOV2 ;
CompTox Dashboard (EPA)	DTXSID1029122 ;
	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 Key: CHIHQLCVLOXUJW-UHFFFAOYSA-N ;
	SMILES c1ccc(cc1)C(=O)OC(=O)c2ccccc2;
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)	2 1 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

Benzoic anhydride is the organic compound with the formula (C₆H₅CO)₂O. It is 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

"Sciencelab msds". Archived from the original on 2016-03-04. Retrieved 2015-12-26.
"aldrich product page".
H. T. Clarke and E. J. Rahrs (1923). "Benzoic Anhydride". Org. Synth. 3: 21. doi:10.15227/orgsyn.003.0021.CS1 maint: uses authors parameter (link)

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[1] "Sciencelab msds". Archived from the original on 2016-03-04. Retrieved 2015-12-26.

[2] "aldrich product page".

[3] H. T. Clarke and E. J. Rahrs (1923). "Benzoic Anhydride". Org. Synth. 3: 21. doi:10.15227/orgsyn.003.0021.CS1 maint: uses authors parameter (link)