320102

Acetic anhydride

ReagentPlus^®, ≥99%

• Synonym(s): Acetanhydride, Acetic acid anhydride, Acetyl acetate, Acetyl anhydride, Ethanoic anhydride
• 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

Properties

• 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

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.

Legal Information

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

Safety Information

• Pictograms: GHS02,GHS06,GHS05
• Signal Word: Danger
• Hazard Statements: H226,H302,H314,H330
• Precautionary Statements: P210 - P280 - P301 + P312 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• 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