Acetic formic anhydride

Acetic formic anhydride is an organic compound with the, which can be viewed as the mixed anhydride of acetic acid and formic acid. It is used on a laboritory-scale as a formylating agent.[1]

Acetic formic anhydride
Skeletal formula of acetic formic anhydride
Ball-and-stick model of the acetic formic anhydride molecule
Names
Preferred IUPAC name
Acetic formic anhydride
Other names
  • Acetyloxymethanone
  • Formyl acetate
  • Formic acetic anhydride
  • ethanoic methanoic anhydride
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C3H4O3/c1-3(5)6-2-4/h2H,1H3 checkY
    Key: ORWKVZNEPHTCQE-UHFFFAOYSA-N checkY
  • CC(=O)OC=O
Properties
C3H4O3
Molar mass 88.062 g·mol−1
Appearance colourless liquid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Preparation

Acetic formic anhydride can be produced by reacting sodium formate with acetyl chloride in anhydrous diethyl ether between 23–27 °C.[2] It can also be prepared by the reaction of acetic anhydride and formic acid at 0 °C.

Properties

While more stable than formic anhydride, acetic formic anhydride is thermally unstable and gradually decomposes above about 60℃, with the evolution of carbon monoxide.[3] Impurities such as pyridine or residual acid can promote this, resulting in decomposition commencing as low as 0°C. Crude material has been successfully purified by distillation at ≤30°C under reduced pressure.[3]

Applications

Acetic formic anhydride is a formylation agent for amines, amino acids, and alcohols. It is also a starting material for other compounds such as formyl fluoride.[2][1]

See also

References
  1. Strazzolini, Paolo; Giumanini, Angelo G.; Cauci, Sabina (1990). "Acetic formic anhydride a review". Tetrahedron. 46 (4): 1081–1118. doi:10.1016/S0040-4020(01)86676-X.
  2. Krimen, Lewis I. (1970). "Acetic Formic Anhydride". Organic Syntheses. 50: 1. doi:10.15227/orgsyn.050.0001.
  3. Muramatsu, Ichiro; Murakami, Masahiro; Yoneda, Takahiro; Hagitani, Akira (February 1965). "The Formylation of Amino Acids with Acetic Formic Anhydride". Bulletin of the Chemical Society of Japan. 38 (2): 244–246. doi:10.1246/bcsj.38.244.
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