1,2,3-Triazole

1,2,3-Triazole

Names
IUPAC name 1H-1,2,3-triazole
Other names 1,2,3-triazole
Identifiers
CAS Number	288-36-8 N
ChEBI	CHEBI:35566 Y
ChemSpider	60839 Y
Jmol interactive 3D	Image Image
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
SMILES C1=CN=NN1 c1cnn[nH]1
Properties
Chemical formula	C2H3N3
Molar mass	69.0654
Appearance	colorless liquid
Density	1.192
Melting point	23 to 25 °C (73 to 77 °F; 296 to 298 K)
Boiling point	203 °C (397 °F; 476 K)
Solubility in water	very soluble
Acidity (pKa)	1.2
Basicity (pKb)	9.4
Related compounds
Related compounds	1,2,4-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

1,2,3-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.^[1]

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, including pharmaceutical drugs such as tazobactam.

References

1. ↑ Heterocyclic chemistry T.L. Gilchrist ISBN 0-582-01421-2