Acetic formic anhydride is an organic compound with the chemical formula C
3H
4O
3, 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.[1]
Names | |
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Preferred IUPAC name
Acetic formic anhydride | |
Other names
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3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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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
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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.
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.[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]
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]