Malonic anhydride

Malonic anhydride

Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name Oxetane-2,4-dione
Other names Malonic anhydride
Identifiers
CAS Number	15159-48-5  Y
3D model (JSmol)	Interactive image
ChemSpider	8351595  Y
PubChem CID	10176090
UNII	V8PB6RYA8G  Y
CompTox Dashboard (EPA)	DTXSID00436365
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
SMILES O=C1OC(=O)C1
Properties
Chemical formula	C3H2O3
Molar mass	86.046 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y  verify  (what is  YN ?) 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]}

See also

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

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): 265–269. doi:10.1023/A:1009270411806. ISSN   1040-0400. S2CID   92816468.
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.