1,2,3-Triazole

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1,2,3-Triazole
Names
Preferred IUPAC name
1H-1,2,3-Triazole
Other names
1,2,3-Triazole
Identifiers
3D model (
JSmol
)
ChEBI
ChemSpider
ECHA InfoCard
 100.128.405 Edit this at Wikidata
EC Number
  • 608-262-3
UNII
  • 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[1]
Basicity (pKb) 1.2[1]
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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1,2,3-Triazole is one of a pair of

heterocycle.[2]

Synthesis

The unsubstituted ring can be produced by an oxidative coupling of glyoxal, hydrazine and sodium nitrite.[3]

A wide range of methods exist for forming substituted 1,2,3-triazoles.

1,3-dipolar cycloaddition reaction. Under thermal conditions, regioselectivity is substrate dependent. Selectivity can be increased with metal catalysts, which have the added benefit of reacting without excessive or extensive heating. Copper catalyzed cycloadditions favor 1,4-disubstituted triazoles, Ruthenium catalyzed cycloaddition favor 1,5-disubstituted triazoles. This chemistry was expanded by Zhu et al. in 2018 wherein they report a two-step sequence from a terminal alkyne to 4-cyano 1,5-disubstituted triazoles. [5]

Properties

The 2H-1,2,3-triazole tautomer is the major form in aqueous solution.[6] It is a surprisingly stable structure compared to other organic compounds with three adjacent nitrogen atoms. However, flash vacuum

ring–chain tautomerism. One manifestation is found in the Dimroth rearrangement
.

Applications

1,2,3-Triazole finds use in research as a bioisostere in medicinal chemistry[7] building block for more complex chemical compounds, including pharmaceutical drugs such as mubritinib and tazobactam.

References

  1. ^ a b "1,2,3-triazole - an overview". Comprehensive Heterocyclic Chemistry. 1984.
  2. ISBN 0-582-01421-2
    .
  3. doi:10.1021/acs.oprd.4c00020
    .
  4. doi:10.1070/RC2005v074n04ABEH000893
    .
  5. PMID 29630830
    .
  6. doi:10.1039/P29890001903
    .
  7. PMID 28676407
    .
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