Description
1,2,3-1H-Triazole is a kind of azole compound. It can effectively promote the proton conduction in polymer electrolyte membranes via an intermolecular proton-transfer mechanism. It is also a useful triazole for proteomics research
1. It also find use in research as a bioisostere in medicinal chemistry as well as an building block for more complex chemical compounds, including pharmaceutical drugs such as mubritinib and tazobactam
2. It is a main class of hetero-cycles because of its extensive range of biological properties such as antimicrobial, anticancer, anti-tubercular, anti-HIV, antimalarial, antibacterial, antifungal, antiviral and anti-diabetic property
3.
Chemical Properties
clear colorless liquid
Uses
It effectively promotes the proton conduction in polymer electrolyte membranes via an intermolecular proton-transfer mechanism. A useful triazole for proteomics research
Uses
A basic 5-membered aromatic heterocycle used as a building block for more complex pharmaceutical compounds. There have been recent studies that showed antitumor, antiinflammatory, analgesic, antifunga
l, antibacterial and antiviral activities in bioactive triazoles.
Definition
ChEBI: 1H-1,2,3-triazole is a 1,2,3-triazole. It is a tautomer of a 2H-1,2,3-triazole and a 4H-1,2,3-triazole.
Synthesis Reference(s)
The Journal of Organic Chemistry, 62, p. 9177, 1997
DOI: 10.1021/jo971313o
General Description
2
H-1,2,3-triazole is tautomeric form of 1
H-1,2,3-triazole. 1
H-1,2,3-triazole effectively promotes the proton conduction in polymer electrolyte membranes via an intermolecular proton-transfer mechanism.
Synthesis
General procedure for the synthesis of 1,2,3-triazole from 1H-1,2,3-triazole-4,5-dicarboxylic acid: to a 2000 mL four-neck flask was added 1250 mL of pure water and 157.08 g (1.0 mol) of 1H-1,2,3-triazole-4,5-dicarboxylic acid, followed by the addition of 4.71 g (equivalent to 1H-1,2,3-triazole-4,5-dicarboxylic acid 3% by mass) of N,N-diisopropylethylamine. The reaction mixture was heated to 100~110°C under atmospheric pressure and refluxed until the reaction solution was clarified. Refluxing was continued for 1 h. The reaction was monitored by HPLC and terminated when the residue of 1H-1,2,3-triazole-4,5-dicarboxylic acid was less than 1%. After completion of the reaction, filtration was performed. A vacuum pump was used to remove most of the water from the filtrate, which was then replaced with a mechanical pump for high vacuum dehydration. The four-necked flask was mounted on a distillation apparatus and vacuum distillation was carried out, resulting in 66.48 g of 1H-1,2,3-triazole with a molar yield of 96.25% and a GC purity of 99.56%.
References
[1] Patent: CN106946803, 2017, A. Location in patent: Paragraph 0035; 0040; 0041; 0045; 0046; 0050; 0051
[2] Patent: CN105330607, 2016, A. Location in patent: Paragraph 0033; 0034
[3] Chemische Berichte, 1893, vol. 26, p. 2737
