Furazan
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| Names | |||
|---|---|---|---|
| IUPAC name
1,2,5-oxadiazole | |||
| Identifiers | |||
288-37-9  | |||
| ChemSpider | 60840 | ||
| Jmol interactive 3D | Image | ||
| PubChem | 67517 | ||
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| Properties | |||
| C2H2N2O | |||
| Molar mass | 70.05008 | ||
| Boiling point | 98 °C (208 °F; 371 K) | ||
| 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 | |||
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.[1] 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
- ↑ Lyell C. Behr and John T. Brent (1963). "Dimethylfurazan". Org. Synth.; Coll. Vol. 4, p. 342
This article incorporates text from a publication now in the public domain: Chisholm, Hugh, ed. (1911). Encyclopædia Britannica (11th ed.). Cambridge University Press.