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320102

Sigma-Aldrich

Acetic anhydride

ReagentPlus®, ≥99%

Synonyme(s) :

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

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100 ML
29,80 €
500 ML
65,30 €
1 L
91,80 €

About This Item

Formule linéaire :
(CH3CO)2O
Numéro CAS:
108-24-7
Poids moléculaire :
102.09
Beilstein:
385737
Numéro CE :
203-564-8
Numéro MDL:
MFCD00008705
Code UNSPSC :
12352100
ID de substance PubChem :
24859248
Nomenclature NACRES :
NA.21

29,80 €

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Densité de vapeur

3.5 (vs air)

Niveau de qualité

200

Pression de vapeur

10 mmHg ( 36 °C)
4 mmHg ( 20 °C)

Gamme de produits

ReagentPlus®

Essai

≥99%

Forme

liquid

Température d'inflammation spontanée

629 °F

Limite d'explosivité

10.3 %

Indice de réfraction

n20/D 1.390 (lit.)

pb

138-140 °C (lit.)

Pf

−73 °C (lit.)

Solubilité

water: slightly soluble

Densité

1.08 g/mL (lit.)

Groupe fonctionnel

anhydride
ester

Chaîne SMILES 

CC(=O)OC(C)=O

InChI

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

Clé InChI

WFDIJRYMOXRFFG-UHFFFAOYSA-N

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Catégories apparentées

Description générale

Acetic anhydride is a carboxylic acid anhydride commonly used as an acetylating agent for amines and alcohols.[1]
Acetic anhydride participates in the Friedel-Craft′s intramolecular cyclization reaction of cyclopropyl ketones to afford the tetralones.[2] It has been reported to promote the Knoevenagel condensation of various aldehydes and activated methylene compounds.[3]

Application

Acetic anhydride may be used as a reactant to synthesize:
  • 3-acetoxybenzoic acid by reacting with 3-hydroxybenzoic acid[4]
  • 6-dimethylamino-2,3-naphthalenedicarboxylic anhydride, a precursor to prepare 6-dimethylaminonaphthalimide[5]

Acetic anhydride was used in the following studies:
  • Lipozyme TL IM (commercial immobilized lipase from Thermomyces lanuginosus) catalyzed acetylation of essential clove oil.[6]
  • As acetyl donor to investigate the lipase catalyzed acetylation of nanofibrillated cellulose (NFC).[7]
  • Synthesis of N-substituted pyrazolines.[8]
  • Acetylation of Barnyardgrass (Echinochloa crus-galli) starch.[9]

Informations légales

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

Pictogrammes

FlameSkull and crossbonesCorrosion
GHS02,GHS06,GHS05

Mention d'avertissement

Danger

Mentions de danger

H226,H302,H314,H330

Classification des risques

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

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

120.2 °F - closed cup

Point d'éclair (°C)

49 °C - closed cup

Équipement de protection individuelle

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

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Certificats d'analyse (COA)

Lot/Batch Number
SDBB2312
STBL1839
SDBB0959
MKCW6876
STBL2691

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Consulter la Bibliothèque de documents

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).
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)
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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Articles

Friedel–Crafts Acylation

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

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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