78766-53-7

Basic information

• Product Name: 5-chloro-1-p-tolyl-1H-1,2,3-benzotriazole
• Synonyms: 5-chloro-1-p-tolyl-1H-1,2,3-benzotriazole
• CAS NO: 78766-53-7
• Molecular Weight: 243.695
• Mol File: 78766-53-7.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 5-chloro-1-p-tolyl-1H-1,2,3-benzotriazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-chloro-1-p-tolyl-1H-1,2,3-benzotriazole(78766-53-7)
• EPA Substance Registry System: 5-chloro-1-p-tolyl-1H-1,2,3-benzotriazole(78766-53-7)

Safety Data

• Hazardous Substances Data: 78766-53-7(Hazardous Substances Data)

Upstream product

• 32724-91-7 (4-chloro-2-nitro-phenyl)-p-tolyl-amine 
• 5720-05-8 4-methylphenylboronic acid 
• 26198-19-6 6-chloro-1-hydroxybenzotriazole 

Relevant articles and documents

The Disappearing Director: The Case of Directed N-Arylation via a Removable Hydroxyl Group

A facile and broadly applicable method for the regiospecific N-arylation of benzotriazoles is reported. Copper-mediated reactions of diverse 1-hydroxy-1H-benzotriazoles with aryl boronic acids lead to 1-aryl-1H-benzotriazole 3-oxides. A N1-OH→N3 prototropy in the 1-hydroxy-1H-benzotriazoles is plausibly the underlying basis, where the tautomer is captured by the boronic acid, leading to C?N (not C?O) bond formation. Because the N?O bond in amine N-oxides and 1-hydroxy-1H-benzotriazoles can be easily reduced by diboron reagents such as (pinB)2 and B2(OH)4, exposure of the 1-aryl-1H-benzotriazole 3-oxides to B2(OH)4 then leads to facile reduction of the N?O bond resulting in diverse, regiospecifically-arylated benzotriazoles. Thus, the N-hydroxyl group in 1-hydroxy-1H-benzotriazoles acts as a disposable arylation director. (Figure presented.).