Furazan

Furazan

Skeletal formula of furazan with numbering convention for substituent groups
Skeletal formula of furazan Space-filling model of the furazan molecule
Names
IUPAC name 1,2,5-oxadiazole
Identifiers
CAS Number	288-37-9 Y
ChemSpider	60840 Y
Jmol 3D model	Interactive image
PubChem	67517
InChI InChI=1S/C2H2N2O/c1-2-4-5-3-1/h1-2H Y Key: JKFAIQOWCVVSKC-UHFFFAOYSA-N Y InChI=1/C2H2N2O/c1-2-4-5-3-1/h1-2H Key: JKFAIQOWCVVSKC-UHFFFAOYAZ
SMILES n1oncc1
Properties
Chemical formula	C2H2N2O
Molar mass	70.05008
Boiling point	98 °C (208 °F; 371 K)
Vapor pressure	{{{value}}}
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

Furazan, or 1,2,5-oxadiazole, is an heterocyclic aromatic organic compound consisting of a five-atom ring containing 1 oxygen and 2 nitrogen atoms. The furazan ring system is also found in the steroid furazabol. Furazan and its derivatives are obtained from the oxime derivatives of 1,2-diketones.

Derivatives

3,4-Dimethylfurazan

3,4-Dimethylfurazan (b.p. 154–159 °C) is prepared by dehydrating dimethylglyoxime. A variety of related derivatives are known, including diphenyl- and methylethylfurazan.

Carboxylic acid derivatives

Potassium permanganate oxidizes 3,4-dimethylfurazan first to methylfurazancarboxylic acid and then to furazandicarboxylic acid. By warming oxyfurazan acetic acid with excess of potassium permanganate, oxyfurazancarboxylic acid is obtained. It crystallizes as prisms (m.p. 175 °C). Furazancarboxylic acid (m.p. 107 °C) is prepared by oxidation of furazanpropionic acid with potassium permanganate. It dissolves in base to give nitrosocyanacetate.

Diaminofurazan

The energetic precursor, diaminofurazan, can be prepared by heating diaminoglyoxime with potassium hydroxide followed by cooling to give white crystals. Like many other furazans, diaminofurazan forms stable complexes with copper(II) salts.

References

•  This article incorporates text from a publication now in the public domain: