1,2,4-Triazole

From Wikipedia, the free encyclopedia
  (Redirected from 1,2,4-triazole)
Jump to navigation Jump to search
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
ChEMBL
ChemSpider
ECHA InfoCard 100.005.476
Properties
C2H3N3
Molar mass 69.00725
Appearance white solid
Melting point 120 to 121 °C (248 to 250 °F; 393 to 394 K)
Boiling point 260 °C (500 °F; 533 K)
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).
☑Y verify (what is ☑Y☒N ?)
Infobox references

1,2,4-Triazole (as ligand in coordination compounds, Htrz abbreviation is sometimes used) 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] 1,2,4-Triazoles can be prepared using the Einhorn–Brunner reaction or the Pellizzari reaction.

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

The ring structure appears in certain N-heterocyclic carbenes.

Application[edit]

Used in the preparation of a plenty 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.