1,2,3-Triazole
From Wikipedia, the free encyclopedia
| 1,2,3-Triazole | |
|---|---|
 |
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| 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 |
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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, such as pharmaceutical drugs like tazobactam.
[edit] References
- ^ Heterocyclic chemistry T.L. Gilchrist ISBN 0-582-01421-2
