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Furazan



Furazan
IUPAC name 1,2,5-oxadiazole
Identifiers
CAS number 288-37-9
PubChem 67517
SMILES C1=NON=C1
Properties
Molecular formula C2H2N2O
Molar mass 70.05008
Boiling point

98 °C, 371 K, 208 °F

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Furazan, or 1,2,5-oxadiazole, is an heterocyclic aromatic organic compound with a five-atom ring containing two oxygen and one nitrogen atom. Furazan and its derivatives are obtained by heating glyoximes (dioximes of ortho-diketones) with alkalis or ammonia.

Additional recommended knowledge

Derivatives

3,4-Dimethylfurazan is prepared by heating dimethylglyoxime with an excess of ammonia for six hours at 165 °C. A liquid at ordinary temperature, it boils at 156 °C. Potassium permanganate oxidizes it first to methylfurazancarboxylic acid and then to furazandicarboxylic acid. Methylethylfurazan and diphenylfurazan are also known. By warming oxyfurazan acetic acid with excess of potassium permanganate to 100 °C, oxyfurazancarboxylic acid is obtained. It crystallizes in prisms, which melt at 175 °C. Furazancarboxylic acid is prepared by the action of a large excess of potassium permanganate on a hot solution of furazanpropionic acid. It melts at 107 °C, and dissolves in caustic soda, with a deep yellow color and formation of nitrosocyanacetic acid.

The furazan ring system is also found in the steroid furazabol.

References

  • This article incorporates text from the Encyclopædia Britannica Eleventh Edition, a publication now in the public domain.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Furazan". A list of authors is available in Wikipedia.
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