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Safety Information

385980

Sigma-Aldrich

Benzoic anhydride

≥95%

Synonym(s):

Benzoyl anhydride, Benzoyl benzoate, Bis(phenylcarbonyl)ether

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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

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.
  • Coupling reagent in the synthesis of macrolactones.
  • Acylating reagent for acylating sulfonamides, amines, alcohols, and phenols using ZSM-5-SO3H as a catalyst.

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

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

385980-BULK:
385980-100G:
385980-VAR:
385980-500G:


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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)
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)
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)
W J Gelsema et al.
Journal of lipid research, 37(6), 1224-1233 (1996-06-01)
Benzoolysis experiments are reported in which diacylglycerophosphocholine is heated at 100 degrees C with benzoic anhydride for variable periods of time. It is shown that more than 90% of the phospholipid is dephosphorylated after 5 h of heating. Lipid extracts

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