1,2,3-Triazole

1,2,3-Triazole

Chembox new
ImageFileL1 = 1%2C2%2C3-triazole_numbering.png ImageSizeL1 = 100px
ImageFileR1 = 1%2C2%2C3-Triazole3d.png ImageSizeR1 = 100px
IUPACName = 1H-1,2,3-triazole
OtherNames = 1,2,3-triazole
Section1 = Chembox Identifiers
CASNo = 288-36-8
PubChem =
SMILES = C1 = CN = NN1
Section2 = Chembox Properties
Formula = C2H3N3
MolarMass = 69.0654
Appearance = colorless liquid
Density = 1.192
MeltingPt = 23-25
BoilingPt = 203
Solubility = very soluble
pKa = 1.2
pKb = 9.4
Section7 = Chembox Hazards
MainHazards =
FlashPt =
Autoignition =
Section8 = Chembox Related
OtherCpds = 1,2,4-triazole imidazole

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

References


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  • Triazole — (Htrz) refers to either one of a pair of isomeric chemical compounds with molecular formula C2H3N3, having a five membered ring of two carbon atoms and three nitrogen atoms.The two isomers are: *1,2,3 Triazole *1,2,4 Triazole DerivativesThe… …   Wikipedia

  • triazole — [trī′ə zōl΄, trī az′ōl] n. [ TRI + AZOLE] 1. any of four isomeric heterocyclic azoles, C2H3N3, having three nitrogen atoms in the ring 2. any derivative of these …   English World dictionary

  • Triazole — Als Triazole werden heterocyclische aromatische Verbindungen mit der Formel C2H3N3 bezeichnet, welche einen fünfatomigen Ring mit zwei Kohlenstoff und drei Stickstoff Atomen enthalten. Inhaltsverzeichnis 1 Isomere 2 Verwendung 3 …   Deutsch Wikipedia

  • Triazole — Les triazoles sont des molécules comportant un cycle à 5 pièces, comportant deux double liaisons et 3 atomes d azote. Elles sont aromatiques et font partie des cycles excédentaires en électrons. Selon la position des atomes d azote, on distingue… …   Wikipédia en Français

  • triazole — triazolas statusas T sritis chemija apibrėžtis Penkianaris heterociklinis junginys. formulė C₂H₃N₃ atitikmenys: angl. triazole rus. триазол …   Chemijos terminų aiškinamasis žodynas

  • triazole — triazolic /truy euh zol ik/, adj. /truy euh zohl , truy az ohl/, n. Chem. 1. any of a group of four compounds containing three nitrogen and two carbon atoms arranged in a five membered ring and having the formula C2H3N3. 2. any of a number of… …   Universalium

  • triazole — noun either of two isomeric heterocyclic compounds having a five membered ring with three nitrogen atoms and two double bonds in the ring; any organic derivative of these compounds …   Wiktionary

  • triazole — tri·azole trī ə .zōl n any of a group of compounds that are characterized by a ring composed of two carbon atoms and three nitrogen atoms and that include a number of antifungal agents (as fluconazole) * * * tri·a·zole (triґə zōl) (tri… …   Medical dictionary

  • Triazole — Tri|azo|le die (Plur.): fünfgliedrige Verbindungen, die drei Stickstoffatome im Molekülring enthalten (Chem.) …   Das große Fremdwörterbuch

  • triazole — tri·a·zole …   English syllables

  • triazole — /ˈtraɪəzɒl/ (say truyuhzol), /traɪˈæzɒl/ (say truy azol) noun any of a group of four heterocyclic compounds, C2H3N3, containing three nitrogen and two carbon atoms arranged in a five membered ring …  

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