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Acetic formic anhydride

Chemical compound C3H4O3

Summary

Chemical compound C3H4O3

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

Preparation

Acetic formic anhydride can be produced by reacting sodium formate with acetyl chloride in anhydrous diethyl ether between 23–27 °C. 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 °C, with the evolution of carbon monoxide. 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.

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.

References

References

  1. (1990). "Acetic formic anhydride a review". Tetrahedron.
  2. (1970). "Acetic Formic Anhydride". Organic Syntheses.
  3. (February 1965). "The Formylation of Amino Acids with Acetic Formic Anhydride". Bulletin of the Chemical Society of Japan.
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carboxylic-anhydrides
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