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320102 Sigma-Aldrich

Acetic anhydride

ReagentPlus®, ≥99%

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Properties

grade   ReagentPlus®
vapor density   3.5 (vs air)
vapor pressure   10 mmHg ( 36 °C)
  4 mmHg ( 20 °C)
InChI Key   WFDIJRYMOXRFFG-UHFFFAOYSA-N
assay   ≥99%
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.)

Description

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.

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

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
RIDADR 
UN 1715 3(8) / PGII
WGK Germany 
1
RTECS 
AK1925000
Flash Point(F) 
120.2 °F
Flash Point(C) 
49 °C

Documents

Certificate of Analysis

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Certificate of Origin

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Protocols & Articles

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 m...
Keywords: Acylations, Catalysis, Electrophilic aromatic substitution, Microwave synthesis, Substitutions

Peer-Reviewed Papers
15

References

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