1,2,4-Triazole

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1,2,4-Triazole
File:1,2,4-triazole numbering.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 Edit this at Wikidata
  • InChI=1S/C2H3N3/c1-3-2-5-4-1/h1-2H,(H,3,4,5) checkY
    Key: NSPMIYGKQJPBQR-UHFFFAOYSA-N checkY
  • InChI=1/C2H3N3/c1-3-2-5-4-1/h1-2H,(H,3,4,5)
    Key: NSPMIYGKQJPBQR-UHFFFAOYAZ
  • N1C=NC=N1
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).
checkY verify (what is checkY☒N ?)

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

Used in the preparation of a plenty of pharmaceuticals:

  1. Anastrozole
  2. Cloridarol
  3. Epoxiconazole
  4. Fluconazole
  5. Fluotrimazole
  6. Flusilazole
  7. Letrozole
  8. Loreclezole
  9. Myclobutanil
  10. Posaconazole
  11. Rizatriptan
  12. Saperconazole
  13. Vibunazole
  14. Vorozole

References

  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.
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