Malonic anhydride

Malonic anhydride
IUPAC name Oxetane-2,4-dione
Other names Malonic anhydride
Identifiers
PubChem	10176090
ChemSpider	8351595 Y
Jmol-3D images	Image 1
SMILES O=C1OC(=O)C1
InChI InChI=1S/C3H2O3/c4-2-1-3(5)6-2/h1H2 Y Key: KKHUSADXXDNRPW-UHFFFAOYSA-N Y InChI=1/C3H2O3/c4-2-1-3(5)6-2/h1H2 Key: KKHUSADXXDNRPW-UHFFFAOYAB
Properties
Molecular formula	C3H2O3
Molar mass	86.05 g mol−1
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Malonic anhydride or oxetane-2,4-dione is an organic compound with chemical formula C₃H₂O₃ or CH₂(CO)₂O. It can be viewed as the anhydride of malonic acid, or a double ketone of oxetane.

Malonic anhydride was first synthesized in 1988 by ozonolysis of diketene.^[1][2] Some derivatives, such as 3,3-dimethyl-oxetane-2,4-dione, are known.^[3][4][5]

References

1. ^ Cotton, F. A.; Wilkinson, G. (1988) Advanced Inorganic Chemistry, 5th edn. Wiley
2. ^ H. Mark Perks and Joel F. Liebman (2000). "Paradigms and Paradoxes: Aspects of the Energetics of Carboxylic Acids and Their Anhydrides". Structural Chemistry 11 (4): 265269. doi:10.1023/A:1009270411806. ISSN 1040-0400. 
3. ^ Charles L. Perrin; Arrhenius, T (1978). J. Am. Chem. SOC. volume 100, pages 5249-5251.
4. ^ Ribeiro da Silva, M. A. J.; Monte, M. J. S.; Ribeiro, J. R.(1999) J. Chem.Thermodyn. 31, 1093.
5. ^ Charles L. Perrin, Douglas Magde, Sylvia J. Berens, Julie Roque (1980), Raman spectrum of a malonic anhydride. (Actually, of 3,3-dimethyl-oxetane-2,4-dione.) J. Org. Chem., volume 45 issue 9, pp 1705–1706. DOI: 10.1021/jo01297a044.

See also

• Carbon suboxide (C₃O₂), an anhydride of malonic anhydride.
• 2-oxetanone, also called β-propiolactone
• 3-oxetanone