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MilliporeSigma

385980

Benzoic anhydride

≥95%

Synonym(s):

Benzoyl anhydride, Benzoyl benzoate, Bis(phenylcarbonyl)ether

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100 G

$46.80

500 G

$117.00

$46.80


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About This Item

Linear Formula:
(C6H5CO)2O
CAS Number:
Molecular Weight:
226.23
Beilstein/REAXYS Number:
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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This Item
348562235598217808
assay

≥95%

assay

95%

assay

95%

assay

95%

Quality Level

200

Quality Level

-

Quality Level

100

Quality Level

200

mp

38-42 °C (lit.)

mp

-

mp

-

mp

75-78 °C (lit.)

form

solid

form

liquid

form

powder

form

-

density

1.199 g/mL at 25 °C (lit.)

density

0.934 g/mL at 25 °C (lit.)

density

-

density

-

functional group

anhydride

functional group

anhydride, ester

functional group

-

functional group

-

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

signalword

Danger

Hazard Classifications

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

target_organs

Lungs

Storage Class

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

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves


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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)
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)
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)
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

Questions

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    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/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    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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