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320102

Sigma-Aldrich

Acetic anhydride

ReagentPlus®, ≥99%

Sinónimos:

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

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About This Item

Fórmula lineal:
(CH3CO)2O
Número de CAS:
108-24-7
Peso molecular:
102.09
Beilstein:
385737
Número CE:
203-564-8
Número MDL:
MFCD00008705
Código UNSPSC:
12352100
ID de la sustancia en PubChem:
24859248
NACRES:
NA.21

densidad de vapor

3.5 (vs air)

Nivel de calidad

200

presión de vapor

10 mmHg ( 36 °C)
4 mmHg ( 20 °C)

Línea del producto

ReagentPlus®

Ensayo

≥99%

Formulario

liquid

temp. de autoignición

629 °F

lim. expl.

10.3 %

índice de refracción

n20/D 1.390 (lit.)

bp

138-140 °C (lit.)

mp

−73 °C (lit.)

solubilidad

water: slightly soluble

densidad

1.08 g/mL (lit.)

grupo funcional

anhydride
ester

cadena SMILES

CC(=O)OC(C)=O

InChI

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

Clave InChI

WFDIJRYMOXRFFG-UHFFFAOYSA-N

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Descripción general

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.

Aplicación

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.

Información legal

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

Palabra de señalización

Danger

Frases de peligro

H226,H302,H314,H330

Clasificaciones de peligro

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

Código de clase de almacenamiento

3 - Flammable liquids

Clase de riesgo para el agua (WGK)

WGK 1

Punto de inflamabilidad (°F)

120.2 °F - closed cup

Punto de inflamabilidad (°C)

49 °C - closed cup

Equipo de protección personal

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

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Certificados de análisis (COA)

Lot/Batch Number
SDBB2312
STBL1839
SDBB0959
MKCW6876
STBL2691

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Sigma-Aldrich

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Sigma-Aldrich

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Acetic Anhydride Meets ACS Specifications, Meets Reagent Specifications for testing USP/NF monographs GR ACS

Supelco

AX0080

Acetic Anhydride

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)
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
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).
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
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Friedel–Crafts Acylation

Friedel-Crafts acylation with Lewis acid catalysts forms monoacylated products via electrophilic aromatic substitution of arenes.

Friedel–Crafts Acylation

Friedel-Crafts acylation with Lewis acid catalysts forms monoacylated products via electrophilic aromatic substitution of arenes.

Friedel–Crafts Acylation

Friedel-Crafts acylation with Lewis acid catalysts forms monoacylated products via electrophilic aromatic substitution of arenes.

Friedel–Crafts Acylation

Friedel-Crafts acylation with Lewis acid catalysts forms monoacylated products via electrophilic aromatic substitution of arenes.

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