1,2,3-Triazole

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1,2,3-Triazole
IUPAC name 1H-1,2,3-triazole
Other names 1,2,3-triazole
Identifiers
CAS number 288-36-8
SMILES C1 = CN = NN1
Properties
Molecular formula C2H3N3
Molar mass 69.0654
Appearance colorless liquid
Density 1.192
Melting point

23-25

Boiling point

203

Solubility in water very soluble
Acidity (pKa) 1.2
Basicity (pKb) 9.4
Related Compounds
Related compounds 1,2,4-triazole imidazole
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and 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. 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.

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.

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

References


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