1,2,3-Triazole | CAS 288-36-8 | Aromatic Heterocycle

Product Name: 1,2,3-Triazole
CAS No.: 288-36-8
Molecular Formula: C₂H₃N₃

Description

1,2,3-Triazole is one of a pair of isomeric chemical compounds called triazoles, which have a five-membered ring of two carbon atoms and three nitrogen atoms. It is a basic aromatic heterocycle.

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

Properties

• Surprisingly stable structure compared to other organic compounds with three adjacent nitrogen atoms

• Flash vacuum pyrolysis at 500 °C leads to loss of molecular nitrogen (N₂), leaving a three-membered aziridine ring

• Some triazoles undergo relatively easy ring-chain tautomerism (e.g., Dimroth rearrangement)

Applications

• Research as a bioisostere in medicinal chemistry

• Building block for more complex chemical compounds, including pharmaceuticals such as mubritinib and tazobactam

• Side chain for semi-synthetic β-endamide antibiotics

• Intermediate for triamcinolone