Furazan

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Furazan
Furazan numbering.png
Identifiers
CAS number 288-37-9
PubChem 67517
ChemSpider 60840 YesY
Jmol-3D images Image 1
Properties
Molecular formula C2H2N2O
Molar mass 70.05008
Boiling point 98 °C (208 °F; 371 K)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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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[edit]

3,4-Dimethylfurazan[edit]

3,4-Dimethylfurazan (b.p. 154–159 °C) is prepared by dehydrating dimethylglyoxime.[1] A variety of related derivatives are known, including diphenyl- and methylethylfurazan.

Carboxylic acid derivatives[edit]

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[edit]

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[edit]

  1. ^ Lyell C. Behr and John T. Brent (1963), "Dimethylfurazan", Org. Synth. ; Coll. Vol. 4: 342