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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
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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
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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL7123
BCCM0272
BCCM3772
BCCM6358
BCCJ8303

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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)
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)
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)
Isamu Shiina et al.
The Journal of organic chemistry, 69(6), 1822-1830 (2004-04-03)
Various carboxylic esters are obtained at room temperature in excellent yields with high chemoselectivities from nearly equimolar amounts of carboxylic acids and alcohols using 2-methyl-6-nitrobenzoic anhydride with triethylamine by the promotion of a basic catalyst such as 4-(dimethylamino)pyridine. A variety
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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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