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385980

Sigma-Aldrich

Benzoic anhydride

≥95%

Synonym(s):

Benzoyl anhydride, Benzoyl benzoate, Bis(phenylcarbonyl)ether

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100 G
€40.20
500 G
€124.00

About This Item

Linear Formula:
(C6H5CO)2O
CAS Number:
Molecular Weight:
226.23
Beilstein:
516726
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

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Quality Level

Assay

≥95%

form

solid

mp

38-42 °C (lit.)

density

1.199 g/mL at 25 °C (lit.)

functional group

anhydride
ester
phenyl

SMILES string

O=C(OC(=O)c1ccccc1)c2ccccc2

InChI

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

InChI key

CHIHQLCVLOXUJW-UHFFFAOYSA-N

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Application

Benzoic anhydride can be used as a:
  • Condensation reagent in the synthesis of carboxylic esters from carboxylic acids and alcohols.[1]
  • Coupling reagent in the synthesis of macrolactones.[2]
  • Acylating reagent for acylating sulfonamides, amines, alcohols, and phenols using ZSM-5-SO3H as a catalyst.[3]

It can be also used as a reagent for the preparation of benzyl benzoate [4], benzylidene dibenzoate [5], 4-benzoyltoluene [6].

Pictograms

Health hazardCorrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Eye Dam. 1 - Skin Irrit. 2 - STOT RE 1 Inhalation

Target Organs

Lungs

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Formyloxyacetoxyphenylmethane and 1, 1-diacylals as versatile O-formylating and O-acylating reagents for alcohols
Chapman RSL, et al.
Tetrahedron, 74(44), 6442-6452 (2018)
TMEDA: efficient and mild catalyst for the acylation of alcohols, phenols and thiols under solvent-free condition
Kadam ST, et al.
Bull. Korean Chem. Soc., 30(5), 1071-1076 (2009)
Acylations with long-chain acid anhydrides and acyl chlorides over zeolite beta
Bejblova M, et al.
Topics in Catalysis, 52(1-2), 178-184 (2009)
ZSM-5-SO3H: an efficient catalyst for acylation of sulfonamides amines, alcohols, and phenols under solvent-free conditions
Massah AR, et al.
ISRN Organic Chemistry, 2013(10), 2312-2312 (2013)
P Chen et al.
Analytical chemistry, 71(21), 4969-4973 (1999-11-24)
Perbenzoylated sialooligosaccharides were found to be stable derivatives, giving intense signals during the matrix-assisted laser desorption/ionization (MALDI) mass spectrometric analysis in the positive-ion mode. Terminal Neu5NAc alpha 2-->3 and alpha 2-->6Gal units of oligosaccharides undergo characteristic structural changes during benzoylation

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