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320102

Sigma-Aldrich

Acetic anhydride

ReagentPlus®, ≥99%

Sinonimo/i:

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

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About This Item

Formula condensata:
(CH3CO)2O
Numero CAS:
108-24-7
Peso molecolare:
102.09
Beilstein:
385737
Numero CE:
203-564-8
Numero MDL:
MFCD00008705
Codice UNSPSC:
12352100
ID PubChem:
24859248
NACRES:
NA.21

Densità del vapore

3.5 (vs air)

Livello qualitativo

200

Tensione di vapore

10 mmHg ( 36 °C)
4 mmHg ( 20 °C)

Nome Commerciale

ReagentPlus®

Saggio

≥99%

Forma fisica

liquid

Temp. autoaccensione

629 °F

Limite di esplosione

10.3 %

Indice di rifrazione

n20/D 1.390 (lit.)

P. eboll.

138-140 °C (lit.)

Punto di fusione

−73 °C (lit.)

Solubilità

water: slightly soluble

Densità

1.08 g/mL (lit.)

Stringa SMILE

CC(=O)OC(C)=O

InChI

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

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Categorie correlate

Descrizione generale

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.

Applicazioni

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.

Note legali

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

Avvertenze

Danger

Indicazioni di pericolo

H226,H302,H314,H330

Classi di pericolo

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

Codice della classe di stoccaggio

3 - Flammable liquids

Classe di pericolosità dell'acqua (WGK)

WGK 1

Punto d’infiammabilità (°F)

120.2 °F - closed cup

Punto d’infiammabilità (°C)

49 °C - closed cup

Dispositivi di protezione individuale

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

Choose from one of the most recent versions:

Certificati d'analisi (COA)

Lot/Batch Number
STBL1839
SDBB0959
MKCW6876
STBL2691
MKCT2003

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Sigma-Aldrich

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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)
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
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
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
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
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Articoli

Friedel–Crafts Acylation

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

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