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320102

Sigma-Aldrich

Acetic anhydride

ReagentPlus®, ≥99%

Fórmula linear:
(CH3CO)2O
Número CAS:
Peso molecular:
102.09
Beilstein:
385737
Número EC:
Número MDL:
ID de substância PubChem:
NACRES:
NA.21

Nível de qualidade

200

densidade de vapor

3.5 (vs air)

pressão de vapor

10 mmHg ( 36 °C)
4 mmHg ( 20 °C)

linha de produto

ReagentPlus®

teor

≥99%

temperatura de autoignição

629 °F

Lim. expl.

10.3 %

índice de refração

n20/D 1.390 (lit.)

pb

138-140 °C (lit.)

pf

−73 °C (lit.)

solubilidade

water: slightly soluble

densidade

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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Descrição geral

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.

Aplicação

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.

Embalagem

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

Informações legais

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

Palavra indicadora

Danger

Classificações de perigo

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

Perigos de suplementos

Código de classe de armazenamento

3 - Flammable liquids

WGK

WGK 1

Ponto de fulgor (ºF)

120.2 °F - closed cup

Ponto de fulgor (ºC)

49 °C - closed cup

Equipamento de proteção individual

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

Certificado de análise

Certificado de origem

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
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
Acetic anhydride as a synthetic reagent.
Kim DH.
Journal of Heterocyclic Chemistry, 13(2), 179-194 (1976)

Artigos

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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