Acetic formic anhydride
{{Short description|Chemical compound C3H4O3}}
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477238854
| ImageFile = Formic acetic anhydride skeletal.svg
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageSize = 160
| ImageAlt = Skeletal formula of acetic formic anhydride
| ImageFile1 = Acetic-formic-anhydride-3D-balls.png
| ImageSize1 = 180
| ImageAlt1 = Ball-and-stick model of the acetic formic anhydride molecule
| PIN = Acetic formic anhydride
| OtherNames = {{ubl|Acetyloxymethanone|Formyl acetate|Formic acetic anhydride|ethanoic methanoic anhydride}}
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|changed|??}}
| CASNo = 2258-42-6
| PubChem = 75269
| ChemSpiderID = 67812
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| SMILES = CC(=O)OC=O
| StdInChI = 1S/C3H4O3/c1-3(5)6-2-4/h2H,1H3
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ORWKVZNEPHTCQE-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
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|Section2={{Chembox Properties
| C=3 | H=4 | O=3
| Appearance = colourless liquid
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Acetic formic anhydride is an organic compound with the chemical formula {{chem|C|3|H|4|O|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.{{cite journal |last1=Strazzolini |first1=Paolo |last2=Giumanini |first2=Angelo G. |last3=Cauci |first3=Sabina |title=Acetic formic anhydride a review |journal=Tetrahedron |date=1990 |volume=46 |issue=4 |pages=1081–1118 |doi=10.1016/S0040-4020(01)86676-X}}
Preparation
Acetic formic anhydride can be produced by reacting sodium formate with acetyl chloride in anhydrous diethyl ether between 23–27 °C.{{cite journal|last1=Krimen|first1=Lewis I.|title=Acetic Formic Anhydride|journal=Organic Syntheses|date=1970|volume=50|page=1|doi=10.15227/orgsyn.050.0001}}
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.{{cite journal |last1=Muramatsu |first1=Ichiro |last2=Murakami |first2=Masahiro |last3=Yoneda |first3=Takahiro |last4=Hagitani |first4=Akira |title=The Formylation of Amino Acids with Acetic Formic Anhydride |journal=Bulletin of the Chemical Society of Japan |date=February 1965 |volume=38 |issue=2 |pages=244–246 |doi=10.1246/bcsj.38.244|pmid=14263227 }} 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.
See also
References
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