1,2,4-Triazole

1,2,4-Triazole

Names
IUPAC name 1H-1,2,4-triazole
Other names 1,2,4-triazole pyrrodiazole
Identifiers
CAS Number	288-88-0 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:46077 Y
ChEMBL	ChEMBL15571 Y
ChemSpider	8900 Y
ECHA InfoCard	100.005.476
PubChem	9257
InChI InChI=1S/C2H3N3/c1-3-2-5-4-1/h1-2H,(H,3,4,5) Y Key: NSPMIYGKQJPBQR-UHFFFAOYSA-N Y InChI=1/C2H3N3/c1-3-2-5-4-1/h1-2H,(H,3,4,5) Key: NSPMIYGKQJPBQR-UHFFFAOYAZ
SMILES n1cnnc1
Properties
Chemical formula	C2H3N3
Molar mass	69.00725
Appearance	white solid
Melting point	120 to 121
Boiling point	260
Solubility in water	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

• Used in the preparation of Rizatriptan, Letrozole, Vorozole, & Posaconazole.

References