1,2,3-Triazole

1,2,3-Triazole
IUPAC name 1H-1,2,3-triazole
Other names 1,2,3-triazole
Identifiers
CAS number	288-36-8 Y
ChemSpider	60839 Y
ChEBI	CHEBI:35566 Y
Jmol-3D images	Image 1 Image 2
SMILES C1=CN=NN1 c1cnn[nH]1
InChI InChI=1S/C2H3N3/c1-2-4-5-3-1/h1-2H,(H,3,4,5) Y Key: QWENRTYMTSOGBR-UHFFFAOYSA-N Y InChI=1/C2H3N3/c1-2-4-5-3-1/h1-2H,(H,3,4,5) Key: QWENRTYMTSOGBR-UHFFFAOYAF
Properties
Molecular formula	C2H3N3
Molar mass	69.0654
Appearance	colorless liquid
Density	1.192
Melting point	23-25 °C
Boiling point	203 °C, 476 K, 397 °F
Solubility in water	very soluble
Acidity (pKa)	1.2
Basicity (pKb)	9.4
Related compounds
Related compounds	1,2,4-triazole imidazole
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

1,2,3-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. 1,2,3-Triazole is a basic aromatic heterocycle.

Substituted 1,2,3-triazoles can be produced using the azide alkyne Huisgen cycloaddition in which an azide and an alkyne undergo a 1,3-dipolar cycloaddition reaction.

It is a surprisingly stable structure compared to other organic compounds with three adjacent nitrogen atoms. However, flash vacuum pyrolysis at 500 °C leads to loss of molecular nitrogen (N₂) to produce aziridine. Certain triazoles are relatively easy to cleave due to so-called ring-chain tautomerism. One manifestation is found in the Dimroth rearrangement.

1,2,3-Triazole finds use in research as a building block for more complex chemical compounds, such as pharmaceutical drugs like tazobactam.