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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:
93-97-0
Molecular Weight:
226.23
Beilstein:
516726
EC Number:
202-291-1
MDL number:
MFCD00003073
UNSPSC Code:
12352100
PubChem Substance ID:
24864062
NACRES:
NA.22

Assay

≥95%

form

solid

mp

38-42 °C (lit.)

density

1.199 g/mL at 25 °C (lit.)

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
GHS08,GHS05

Signal Word

Danger

Hazard Statements

H315,H318,H372

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
A V Kornilov et al.
Carbohydrate research, 336(4), 309-313 (2001-12-01)
Heating of non-substituted beta-D-glucopyranuronic acids in the presence of pivalic or benzoic anhydride in DMF gives 4-O-monoacylated or 2,4-di-O-acylated 6,3-lactones that can be easily transformed into corresponding methyl uronates bearing free OH-groups at C-2 and C-3 or C-3 only, respectively.
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