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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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100 ML
28,60 €
500 ML
63,10 €
1 L
93,50 €

28,60 €

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100 ML
28,60 €
500 ML
63,10 €
1 L
93,50 €

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

28,60 €

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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.[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]

Aplicación

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]

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
STBL1839
SDBB0959
MKCW6876
STBL2691
MKCT2003

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Visite la Librería de documentos

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)
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
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Artículos

Friedel–Crafts Acylation

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

Preguntas

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

    1 respuesta

    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 respuesta

    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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