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242845

Sigma-Aldrich

Acetic anhydride

ACS reagent, ≥98.0%

Synonym(s):

Acetanhydride, Acetic acid anhydride, Acetyl acetate, Acetyl anhydride, Ethanoic anhydride

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About This Item

Linear Formula:
(CH3CO)2O
CAS Number:
108-24-7
Molecular Weight:
102.09
Beilstein/REAXYS Number:
385737
EC Number:
203-564-8
MDL number:
MFCD00008705
UNSPSC Code:
12352100
PubChem Substance ID:
24854587
NACRES:
NA.21

grade

ACS reagent

Quality Level

200

vapor density

3.5 (vs air)

vapor pressure

10 mmHg ( 36 °C)
4 mmHg ( 20 °C)

assay

≥98.0%

form

liquid

autoignition temp.

629 °F

expl. lim.

10.3 %

impurities

MnO4- reducers, passes test

evapn. residue

≤0.003%

refractive index

n20/D 1.390 (lit.)

bp

138-140 °C (lit.)

mp

−73 °C (lit.)

solubility

H2O: slightly soluble

density

1.08 g/mL (lit.)

anion traces

chloride (Cl-): ≤5 ppm
phosphate (PO43-): ≤0.001%
sulfate (SO42-): ≤5 ppm

cation traces

Fe: ≤5 ppm
heavy metals: ≤2 ppm

functional group

anhydride
ester

SMILES string

CC(=O)OC(C)=O

InChI

1S/C4H6O3/c1-3(5)7-4(2)6/h1-2H3

InChI key

WFDIJRYMOXRFFG-UHFFFAOYSA-N

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General description

Acetic anhydride is an organic solvent. On dissolution in water it undergoes solvolysis to afford acetic acid. It is widely employed for the acetylation of various alcohols. Wacher process (starting reagent + a ketene) and Knapsack process (starting reagent = acetaldehyde) have been reported for the industrial preparation of acetic anhydride.

Application

Acetic anhydride has been used as one of the reaction components in the preparation of:
  • 2-acetylamino-5-aminobenzenesulfonic acid
  • 3,3′-bis(sulfonato)-4,4′-bis(chloroacetamido)azobenzene (BSBCA)
  • 10-acetoxy-9-nitro-octadecanoic acid, allyl ester
  • 9-nitro-oleic acid
It may be used for acetylation of anisole over HBEA zeolite in a batch reactor.

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Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B

Storage Class

3 - Flammable liquids

wgk_germany

WGK 1

flash_point_f

120.2 °F - closed cup

flash_point_c

49 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW3422
MKCV7142
MKCT6254
MKCT3207
MKCQ9026

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Acetylation of anisole by acetic anhydride over a HBEA zeolite-Origin of deactivation of the catalyst.
Rohan D, et al.
J. Catal., 177(2), 296-305 (1998)
Darcy C Burns et al.
Nature protocols, 2(2), 251-258 (2007-04-05)
This protocol describes a procedure for the synthesis of 3,3'-bis(sulfonato)-4,4'-bis(chloroacetamido)azobenzene (BSBCA), a water-soluble, thiol-reactive, photo-switchable cross-linker. In addition, a protocol is outlined for installing the cross-linker in an intramolecular fashion onto proteins bearing two surface-exposed Cys residues. BSBCA is designed
Steven R Woodcock et al.
Free radical biology & medicine, 59, 14-26 (2012-12-04)
Nitrated fatty acids are the product of nitrogen dioxide reaction with unsaturated fatty acids. The discovery of peroxynitrite and peroxidase-induced nitration of biomolecules led to the initial reports of endogenous nitrated fatty acids. These species increase during ischemia/reperfusion, but concentrations
Maciej Podgórski
Dental materials : official publication of the Academy of Dental Materials, 27(8), 748-754 (2011-04-26)
In this study acetyloxypropylene dimethacrylate was synthesized and proposed as an alternative monomer for triethyleneglycol dimethacrylate (TEGDMA) in dental mixtures. The monomer was prepared by the reaction of glycerol dimethacrylate with acetic anhydride. The exchange reaction was carried out in
Lakshmi Pillai-Kastoori et al.
PLoS genetics, 10(7), e1004491-e1004491 (2014-07-11)
Ocular coloboma is a sight-threatening malformation caused by failure of the choroid fissure to close during morphogenesis of the eye, and is frequently associated with additional anomalies, including microphthalmia and cataracts. Although Hedgehog signaling is known to play a critical
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