1-Aminobenzotriazole

Bruce Rickborn

Bruce Rickborn

University of California, Santa Barbara, CA, USA

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First published: 15 April 2001

Abstract

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[1614-12-6] C6H6N4 (MW 134.06)

InChI = 1S/C6H6N4/c7-10-6-4-2-1-3-5(6)8-9-10/h1-4H,7H2

InChIKey = JCXKHYLLVKZPKE-UHFFFAOYSA-N

(an important precursor of benzyne, by oxidation with lead tetraacetate;1 this method of benzyne generation is especially useful for biphenylene formation and other [2 + 2],1c [3 + 2],19 and [4 + 2]22 cycloadditions)

Alternate Name: 1H-benzotriazol-1-amine.

Physical Data: colorless to tan solid, mp 83–84 °C;1c 1H NMR;1c 15N NMR.2

Solubility: sol benzene, CH2Cl2, CHCl3.

Form Supplied in: commercially available.

Preparative Methods: by amination of benzotriazole with Hydroxylamine‐O‐sulfonic Acid, or from o-nitroaniline by a multistep route.1c

Handling, Storage, and Precautions: toxicity and carcinogenicity not known; reacts rapidly with various oxidizing agents to generate benzyne.

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