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 reported the use of these reagents in the preparation of α-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. The presence of a halogen allows these reagents to be used as substrates in various coupling reactions, including Suzuki-Miyaura cross-coupling reactions.

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New Benzotriazole Reagents

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Molecular Formula

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C25201 5-Chlorobenzotriazole 99% C6H4ClN3
440051 1-(Chloromethyl)-1H-benzotriazole 98% C7H6ClN3
596817 1-(3-Chloropropionyl)-1H-benzotriazole 97% C9H8ClN3O
596701 1-(4-Chlorobenzoyl)-1H-benzotriazole 97% C13H8ClN3O
ADE000087 2-Methylacrylic acid 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]-propyl ester AldrichCPR C23H26ClN3O3