1,2,3-Triazole

Names

IUPAC name

1H-1,2,3-triazole

Other names

1,2,3-triazole

Identifiers

288-36-8^N

CHEBI:35566^Y

60839^Y

InChI=1S/C2H3N3/c1-2-4-5-3-1/h1-2H,(H,3,4,5)^Y
Key: QWENRTYMTSOGBR-UHFFFAOYSA-N^Y
InChI=1/C2H3N3/c1-2-4-5-3-1/h1-2H,(H,3,4,5)
Key: QWENRTYMTSOGBR-UHFFFAOYAF

Jmol-3D images

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SMILES

C1=CN=NN1
c1cnn[nH]1

Properties

Chemical formula

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)

Solubility in water

very soluble

Acidity (pK_a)

1.2

Basicity (pK_b)

9.4

Related compounds

1,2,4-triazole imidazole

Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 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, including pharmaceutical drugs such as tazobactam.

References

↑ Heterocyclic chemistry T.L. Gilchrist ISBN 0-582-01421-2