1,2,4-Triazole

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1,2,4-Triazole
1,2,4-triazole numbering.png
1,2,4-Triazole3d.png
Names
IUPAC name
1H-1,2,4-triazole
Other names
1,2,4-triazole pyrrodiazole
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.005.476
Properties
C2H3N3
Molar mass 69.00725
Appearance white solid
Melting point 120 to 121
Boiling point 260
very soluble
Acidity (pKa) 10,3
Basicity (pKb) 11,8
Hazards
Flash point 140 °C (284 °F; 413 K)
Related compounds
Related compounds
1,2,3-triazole imidazole
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

1,2,4-Triazole is one of a pair of isomeric chemical compounds with molecular formula C2H3N3, called triazoles, which have a five-membered ring of two carbon atoms and three nitrogen atoms. 1,2,4-Triazole is a basic aromatic heterocycle. 1,2,4-Triazole derivatives find use in a wide variety of applications, most notably as antifungals such as fluconazole and itraconazole.

1,2,4-Triazoles can be prepared using the Einhorn–Brunner reaction or the Pellizzari reaction.[1]

Unsubstituted 1,2,4-triazole can be prepared from thiosemicarbazide by acyation with formic acid and subsequent cyclization of 1-formyl-3-thiosemicarbazide into 1,2,4-triazole-3(5)-thiol; oxydation of thiol by nitric acid yelds 1,2,4-triazole.[2]

The ring structure appears in certain N-heterocyclic carbenes.

Application[edit]

Used in the preparation of a plethora of pharmaceuticals:

References[edit]

  1. ^ Potts K. T. (1961). "The Chemistry of 1,2,4-Triazoles". Chemical Reviews. 61 (2): 87–127. doi:10.1021/cr60210a001. 
  2. ^ "1,2,4-TRIAZOLE". Organic Syntheses. 40: 99. 1960. doi:10.15227/orgsyn.040.0099. ISSN 0078-6209. Retrieved 2016-07-22.