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320102

Sigma-Aldrich

Acetic anhydride

ReagentPlus®, ≥99%

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:
385737
EC Number:
203-564-8
MDL number:
MFCD00008705
UNSPSC Code:
12352100
PubChem Substance ID:
24859248
NACRES:
NA.21

vapor density

3.5 (vs air)

Quality Level

200

vapor pressure

10 mmHg ( 36 °C)
4 mmHg ( 20 °C)

product line

ReagentPlus®

Assay

≥99%

form

liquid

autoignition temp.

629 °F

expl. lim.

10.3 %

refractive index

n20/D 1.390 (lit.)

bp

138-140 °C (lit.)

mp

−73 °C (lit.)

solubility

water: slightly soluble

density

1.08 g/mL (lit.)

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 a carboxylic acid anhydride commonly used as an acetylating agent for amines and alcohols.
Acetic anhydride participates in the Friedel-Craft′s intramolecular cyclization reaction of cyclopropyl ketones to afford the tetralones. It has been reported to promote the Knoevenagel condensation of various aldehydes and activated methylene compounds.

Application

Acetic anhydride may be used as a reactant to synthesize:
  • 3-acetoxybenzoic acid by reacting with 3-hydroxybenzoic acid
  • 6-dimethylamino-2,3-naphthalenedicarboxylic anhydride, a precursor to prepare 6-dimethylaminonaphthalimide

Acetic anhydride was used in the following studies:
  • Lipozyme TL IM (commercial immobilized lipase from Thermomyces lanuginosus) catalyzed acetylation of essential clove oil.
  • As acetyl donor to investigate the lipase catalyzed acetylation of nanofibrillated cellulose (NFC).
  • Synthesis of N-substituted pyrazolines.
  • Acetylation of Barnyardgrass (Echinochloa crus-galli) starch.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Signal Word

Danger

Hazard Statements

H226,H302,H314,H330

Hazard Classifications

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

120.2 °F - closed cup

Flash Point(C)

49 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBK5431
STBK2228
STBK0644
SHBM1367
STBJ5344

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Mojca Božič et al.
Carbohydrate polymers, 125, 340-351 (2015-04-11)
The acetylation efficiency of nanofibrillated cellulose (NFC) with acetic anhydride as acetyl donor was studied using lipase from Aspergillus niger in a mixture of dimethyl sulphoxide (DMSO) and phosphate buffer solution at ambient conditions and in supercritical carbon dioxide (scCO2).
Yohei Ogiwara et al.
The Journal of organic chemistry, 80(6), 3101-3110 (2015-02-18)
The combination of a catalytic amount of InCl3 and acetic anhydride remarkably promotes the Knoevenagel condensation of a variety of aldehydes and activated methylene compounds. This catalytic system accommodates aromatic aldehydes containing a variety of electron-donating and -withdrawing groups, heteroaromatic
Semi-synthesis and proteasome inhibition of D-ring deoxy analogs of (-)-epigallocatechin gallate (EGCG), the active ingredient of green tea extract.
Huo C, et al.
Journal of Chemistry, 86(6), 495-502 (2008)
Josiane Bartz et al.
Food chemistry, 178, 236-242 (2015-02-24)
Barnyardgrass (Echinochloa crus-galli) is an invasive plant that is difficult to control and is found in abundance as part of the waste of the paddy industry. In this study, barnyardgrass starch was extracted and studied to obtain a novel starch
B Umesha et al.
Bioorganicheskaia khimiia, 40(4), 503-512 (2015-04-23)
The pyrazole analogues of podophyllotoxin were synthesized by the chalcone route. This route attracts the attention because of its simple operating conditions and easy availability ofthe chemicals. Initially, benzylide-neacetophenones (chalcones) were prepared in high yields by Claisen-Schmidt reaction of acetophenones
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Articles

Friedel–Crafts Acylation

The Friedel–Crafts acylation is the reaction of an arene with acyl chlorides or anhydrides using a strong Lewis acid catalyst. This reaction proceeds via electrophilic aromatic substitution to form monoacylated products.

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