Furoxan

Furoxan or 1,2,5-oxadiazole 2-oxide is a heterocycle of the isoxazole family and an amine oxide derivative of furazan. It is a nitric oxide donor.[1] As such, furoxan and its derivatives are actively researched as potential new drugs (Ipramidil) and insensitive high density explosives (4,4’-Dinitro-3,3’-diazenofuroxan).

Furoxan
Names
Preferred IUPAC name
1,2λ5,5-Oxadiazol-2-one
Other names
Furazan N-oxide; Furazan 2-oxide
Identifiers
3D model (JSmol)
ChemSpider
MeSH C528141
  • InChI=1S/C2H2N2O2/c5-4-2-1-3-6-4/h1-2H ☒N
    Key: KCMCIQNPQUSQKQ-UHFFFAOYSA-N ☒N
  • InChI=1/C2H2N2O2/c5-4-2-1-3-6-4/h1-2H
    Key: KCMCIQNPQUSQKQ-UHFFFAOYAH
  • [O-][N+]1=CC=NO1
Properties
C2H2N2O2
Molar mass 86.050 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Furoxanes can be formed by dimerization of nitrile oxides.

References
  1. Clara Cena; Massimo Bertinaria; Donatella Boschi; Marta Giorgis; Alberto Gasco (2006). "Use of the furoxan (1,2,5-oxadiazole 2-oxide) system in the design of new NO-donor antioxidant hybrids" (PDF). Arkivoc (HL-1787GR): 301–309.


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