Acetic formic anhydride
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| Names | |
|---|---|
| Preferred IUPAC name Acetic formic anhydride | |
Other names
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| Identifiers | |
3D model (JSmol) | |
| ChemSpider | |
PubChem CID | |
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). | |
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]
Preparation
[edit]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
[edit]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]
Applications
[edit]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
[edit]References
[edit]- ^ a b 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.
- ^ a b Krimen, Lewis I. (1970). "Acetic Formic Anhydride". Organic Syntheses. 50: 1. doi:10.15227/orgsyn.050.0001.
- ^ a b 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. PMID 14263227.