Malonic anhydride

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

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

Tracking categories (test):

* SizeSet

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): 265–269. 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

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*[CID]: Compound ID