Malonic anhydride

Malonic anhydride
Names
	Preferred IUPAC name Oxetane-2,4-dione
	Other names Malonic anhydride
Identifiers
CAS Number	15159-48-5 ;
3D model (JSmol)	Interactive image;
ChemSpider	8351595 ;
PubChem CID	10176090;
UNII	V8PB6RYA8G ;
CompTox Dashboard (EPA)	DTXSID00436365 ;
	InChI InChI=1S/C3H2O3/c4-2-1-3(5)6-2/h1H2 Key: KKHUSADXXDNRPW-UHFFFAOYSA-N ; 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). verify (what is ?) Infobox references

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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

^ Cotton, F. A.; Wilkinson, G. (1988) Advanced Inorganic Chemistry, 5th edn. Wiley
^ 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.
^ Charles L. Perrin; Arrhenius, T (1978). J. Am. Chem. SOC. volume 100, pages 5249-5251.
^ Ribeiro da Silva, M. A. J.; Monte, M. J. S.; Ribeiro, J. R.(1999) J. Chem.Thermodyn. 31, 1093.
^ 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.

[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.

[1]

[2]

[3]

[4]

[5]

See also

References