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539996

Sigma-Aldrich

Acetic anhydride

99.5%

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Synonym(s):
Acetanhydride, Acetic acid anhydride, Acetyl acetate, Acetyl anhydride, Ethanoic anhydride
Linear Formula:
(CH3CO)2O
CAS Number:
108-24-7
Molecular Weight:
102.09
Beilstein:
385737
EC Number:
203-564-8
MDL number:
MFCD00008705
UNSPSC Code:
12352100
PubChem Substance ID:
24878429
NACRES:
NA.21

vapor density

3.5 (vs air)

Quality Level

200

vapor pressure

10 mmHg ( 36 °C)
4 mmHg ( 20 °C)

Assay

99.5%

autoignition temp.

629 °F

expl. lim.

10.3 %

refractive index

n20/D 1.390 (lit.)

bp

138-140 °C (lit.)

mp

−73 °C (lit.)

solubility

water: slightly soluble

density

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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General description

Acetic anhydride is a carboxylic acid anhydride commonly used for the acetylation of amines and alcohols. It undergoes exothermic reaction on addition of water to form acetic acid. The photodecomposition of acetic anhydride has been studied over the temperature range from 60-160°C. The impact of treating pine wood with acetic anhydride has been investigated to evaluate the toughness of pine wood.

Application

Acetic anhydride has been used in the preparation of 6-dimethylamino-2,3-naphthalenedicarboxylic anhydride. It has also been used to generate acetate ions during high resolution chemical ionization mass spectrometry (CI-ToFMS) analysis.

Signal Word

Danger

Hazard Statements

H226,H302,H314,H330

Hazard Classifications

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

WGK

WGK 1

Flash Point(F)

120.2 °F

Flash Point(C)

49 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Acetic Anhydride Hydrolysis at High Acetic Anhydride to Water Ratios.
Fritzler BC, et al.
International Journal of Chemical Kinetics, 46(3), 151-160 (2014)
Toughness of pine wood chemically modified with acetic anhydride.
Papadopoulos AN and Tountziarakis P.
European Journal of Wood and Wood Products, 70(1-3), 399-400 (2012)
Photolysis of Acetic Anhydride.
Burwasser H and Taylor HA.
J. Chem. Phys. , 23(12), 2295-2299 (1955)
Acetic anhydride as a synthetic reagent.
Kim DH.
Journal of Heterocyclic Chemistry, 13(2), 179-194 (1976)
Kishore Baathulaa et al.
Nature protocols, 6(12), 1990-1997 (2011-12-03)
Environment-sensitive fluorophores have different quantum yields in different solvents. 6-Dimethylaminonaphthalimide (6-DMN), for example, has a low quantum yield in aqueous solutions, but is highly fluorescent in nonpolar solvents or when bound to hydrophobic sites in proteins or membranes. 6-DMN has
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