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320102

Sigma-Aldrich

Acetic anhydride

ReagentPlus®, ≥99%

Linear Formula:
(CH3CO)2O
CAS Number:
Molecular Weight:
102.09
Beilstein:
385737
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.21

Quality Level

vapor density

3.5 (vs air)

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.)

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 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.
Acetic anhydride is a carboxylic acid anhydride commonly used as an acetylating agent for amines and alcohols.

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.

Packaging

1 L in glass bottle
100, 4×100, 500 mL in glass bottle

Legal Information

ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Signal Word

Danger

Hazard Statements

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

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

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
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)
Braulio Insuasty et al.
European journal of medicinal chemistry, 93, 401-413 (2015-03-01)
A new series of chalcones 5a-f were synthesized from caffeine-based aldehyde 3 and substituted acetophenones 4a-f. Treatment of compounds 5a-f with hydrazine hydrate led to pyrazolines 6a-f, and their subsequent reaction with acetic anhydride or formic acid afforded the corresponding
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
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

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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