Benzotriazoles

Benzotriazoles, bicyclic heterocyclic systems containing three nitrogen atoms and a fused benzene ring, show a wide range of biological and pharmacological activities as well as applications in materials science. Benzotriazole can be synthesized using benzene-1,2-diamine and carboxylic acid. Benzotriazoles possess a wide spectrum of biological activities including antibacterial, antifungal, antiviral, anti-inflammatory, antihypertensive, and analgesic properties. Benzotriazoles are used in industry as fixing agents in photographic emulsions, as anti-tarnish agents for copper and its alloys, as a corrosion inhibitor, and in antifreeze and water coolant systems. Some synthetic methods of benzotriazole include N-alkylation of benzotriazole under solvent-free conditions and copper-free “click” methods. The utility of N-acylbenzotriazoles continues to expand. Professor A. R. Katritzky has recently reported the use of these reagents in the preparation of a-nitro ketones, oxazolines and thiazolines under microwave irradiation.

Benzotriazole has been commonly employed as a leaving group and has been used extensively as a novel synthetic auxiliary. Much of its attractiveness lies in its ability to be introduced readily and to be easily removed during synthesis, as well as its ability to activate other parts of the molecule. Katritzky’s group at the University of Florida has performed much of the pioneering work on benzotriazole-mediated synthesis, and continues to provide new methods employing the benzotriazole moiety.

A plethora of methods for the formation of the peptide bond have been reported. The most successful approaches known today involve active ester formation with uronium/guanidinium salts. The most popular members of this family are peptide synthesis reagents based on benzotriazole derivatives such as HOBt or HOAt, both of which are also commonly used as additives in carbodiimide mediated peptide coupling.

Learn More about Benzotriazoles
COMU – Safer and More Efficient Peptide Coupling Reagent
New Benzotriazole Reagents

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361011 1H-1,2,3-Triazolo[4,5-b]pyridine 98% C5H4N4
C25201 5-Chlorobenzotriazole 99% C6H4ClN3
12799 1H-Benzotriazole ≥98.0% (N) C6H5N3
632791 4-Hydroxy-1H-benzotriazole 97% C6H5N3O
CDS000711 5-Amino-1H-benzotriazole AldrichCPR C6H6N4
177679 7-Hydroxy-5-methyl[1,2,4]triazolo[1,5-a]pyrimidine 98% C6H6N4O
304239 Benzotriazole-5-carboxylic acid 99% C7H5N3O2
196304 5-Methyl-1H-benzotriazole 98% C7H7N3
CBR01759 1-Methyl-1H-1,2,3-benzotriazol-4-amine AldrichCPR C7H8N4
CBR01799 1-Methyl-1H-1,2,3-benzotriazol-5-amine AldrichCPR C7H8N4
CBR01757 2-Methyl-2H-1,2,3-benzotriazol-4-amine AldrichCPR C7H8N4
CBR00336 2H-1,2,3-Benzotriazol-2-ylacetic acid AldrichCPR C8H7N3O2
D150002 5,6-Dimethyl-1H-benzotriazole monohydrate 99% C8H9N3 · H2O
CDS002551 2-(2H-1,2,3-Benzotriazol-2-yl)propanoic acid AldrichCPR C9H9N3O2
647357 1-(2-Thienylsulfonyl)-1H-benzotriazole C10H7N3O2S2
647349 1-(2-Pyridinylsulfonyl)-1H-benzotriazole 97% C11H8N4O2S
642584 1-(1-Ethoxy-2-propynyl)-1H-benzotriazole 97% C11H11N3O
CDS000420 Methyl-1H-benzotriazole (mixture) AldrichCPR C14H14N6
ADE000087 2-Methylacrylic acid 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]-propyl ester AldrichCPR C23H26ClN3O3