1,2,3-Triazole

1,2,3-Triazole
Names
IUPAC name
1H-1,2,3-triazole
Other names
1,2,3-triazole
Identifiers
288-36-8 N
ChEBI CHEBI:35566 YesY
ChemSpider 60839 YesY
Jmol interactive 3D Image
Image
Properties
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)
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).
N verify (what is YesYN ?)
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
This article is issued from Wikipedia - version of the Thursday, February 04, 2016. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.