1,2,3-Triazole

Summary

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]

1,2,3-Triazole
1,2,3-triazole numbering.png
1,2,3-Triazole3d.png
Names
Preferred IUPAC name
1H-1,2,3-Triazole
Other names
1,2,3-Triazole
Identifiers
  • 288-36-8 ☒N
3D model (JSmol)
  • Interactive image
  • Interactive image
ChEBI
  • CHEBI:35566 checkY
ChemSpider
  • 60839 checkY
ECHA InfoCard 100.128.405 Edit this at Wikidata
EC Number
  • 608-262-3
  • 67516
  • DTXSID30870495 Edit this at Wikidata
  • InChI=1S/C2H3N3/c1-2-4-5-3-1/h1-2H,(H,3,4,5) checkY
    Key: QWENRTYMTSOGBR-UHFFFAOYSA-N checkY
  • InChI=1/C2H3N3/c1-2-4-5-3-1/h1-2H,(H,3,4,5)
    Key: QWENRTYMTSOGBR-UHFFFAOYAF
  • C1=CN=NN1
  • c1cnn[nH]1
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) 9.4
Basicity (pKb) 1.2
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
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

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) leaving a three-member aziridine ring. Certain triazoles are relatively easy to cleave due to ring–chain tautomerism. One manifestation is found in the Dimroth rearrangement.

1,2,3-Triazole finds use in research as a bioisostere in medicinal chemistry[2] building block for more complex chemical compounds, including pharmaceutical drugs such as mubritinib and tazobactam.

The 2H-1,2,3-triazole tautomer is the major form in aqueous solution.[3]

ReferencesEdit

  1. ^ Gilchrist, T.L. (1987). Heterocyclic chemistry. Prentice Hall Press. ISBN 0-582-01421-2.
  2. ^ Bonandi, E.; Christodoulou, M. S.; Fumagalli, G.; Perdicchia, D.; Rastelli, G.; Passarella, D. (2017). "The 1,2,3-triazole ring as a bioisostere in medicinal chemistry". Drug Discov Today. 22 (10): 1572–1581. doi:10.1016/j.drudis.2017.05.014. PMID 28676407.
  3. ^ Albert, Adrien; Taylor, Peter J. (1989). "The tautomerism of 1,2,3-triazole in aqueous solution". Journal of the Chemical Society, Perkin Transactions 2 (11): 1903–1905. doi:10.1039/P29890001903.