| 1,2,3-Triazole | |
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1H-1,2,3-triazole |
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Other names
1,2,3-triazole |
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| Identifiers | |
| CAS number | 288-36-8 |
| ChemSpider | 60839 |
| ChEBI | CHEBI:35566 |
| Jmol-3D images | Image 1 Image 2 |
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| 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 |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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, such as pharmaceutical drugs like tazobactam.