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Key Documents

8.22278

Sigma-Aldrich

Acetic anhydride

for synthesis

Synonym(s):

Acetic anhydride, Acetyl acetate, Acetyl oxide

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About This Item

Linear Formula:
(CH3CO)2O
CAS Number:
108-24-7
Molecular Weight:
102.09
MDL number:
MFCD00008705
UNSPSC Code:
12352106
EC Index Number:
203-564-8
NACRES:
NA.22

vapor pressure

4 hPa ( 20 °C)

Quality Level

200

Assay

≥98.0% (GC)

form

liquid

autoignition temp.

330 °C

potency

630 mg/kg LD50, oral (Rat)
4320 mg/kg LD50, skin (Rabbit)

expl. lim.

2.0-10.2 % (v/v)

pH

3 (20 °C, 10 g/L in H2O)

mp

-73 °C

transition temp

flash point 49 °C

density

1.08 g/cm3 at 20 °C

storage temp.

2-30°C

InChI

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

InChI key

WFDIJRYMOXRFFG-UHFFFAOYSA-N

General description

Acetic anhydride is a widely used reagent in organic synthesis. The reagent is effective for acetylating alcohols, amines, and thiols. Additionally, it is used in various named reactions such as the Pummerer reaction, the Perkin reaction, the Polonovski reaction, the N-oxide reaction, and the Thiele reaction. Acetic anhydride is an effective reagent during oxidation of alcohols, dehydration, ether cleavage, enol acetate formation, and gem-diacetate formation.

Application

Acetic anhydride is used:
  • In the solvent free acylation of 2-methylfuran to 2-acetyl-5-methylfuran in presence of hydroxide fluorides catalyst.
  • As a catalyst in the synthesis of 3-arylideneisobenzofuran-1(3H)-one derivatives from phthalic anhydride and quinoline derivatives.
  • In the preparation of hyperbranched poly ethoxy siloxanes by condensation reaction with tetra ethoxy silane in presence of an organotitanium catalyst.

Analysis Note

Assay (GC, area%): ≥ 98.0 % (a/a)
Density (d 20 °C/ 4 °C): 1.080 - 1.082
Identity (IR): passes test

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

120.2 °F - closed cup

Flash Point(C)

49 °C - closed cup

Certificates of Analysis (COA)

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Inorganic hydroxide fluorides as solid catalysts for acylation of 2-methylfuran by acetic anhydride
Frouri F, et al.
Applied Catalysis. B, Environmental, 168, 515-523 (2015)
Acetic Anhydride
Regina Zibuck
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
One-pot synthesis of hyperbranched polyethoxysiloxanes
Zhu X, et al.
Macromolecules, 39(5), 1701-1708 (2016)

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