1,2,4-Triazole

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
CAS Number	288-88-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:46077 ;
ChEMBL	ChEMBL15571 ;
ChemSpider	8900 ;
ECHA InfoCard	100.005.476
PubChem CID	9257;
CompTox Dashboard (EPA)	DTXSID6027131 ;
	InChI InChI=1S/C2H3N3/c1-3-2-5-4-1/h1-2H,(H,3,4,5) Key: NSPMIYGKQJPBQR-UHFFFAOYSA-N ; InChI=1/C2H3N3/c1-3-2-5-4-1/h1-2H,(H,3,4,5) Key: NSPMIYGKQJPBQR-UHFFFAOYAZ;
	SMILES N1C=NC=N1;
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). verify (what is ?) 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 a plethora of pharmaceuticals:

References

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

[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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