25877-73-0

Basic information

• Product Name: 5-Phenyl-1H-benzo[d][1,2,3]triazole
• Synonyms: 5-Phenyl-1H-benzo[d][1,2,3]triazole;5-Phenyl-1H-benzotriazole
• CAS NO: 25877-73-0
• Molecular Formula: C₁₂H₉N₃
• Molecular Weight: 195.21996
• Mol File: 25877-73-0.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-Phenyl-1H-benzo[d][1,2,3]triazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Phenyl-1H-benzo[d][1,2,3]triazole(25877-73-0)
• EPA Substance Registry System: 5-Phenyl-1H-benzo[d][1,2,3]triazole(25877-73-0)

Safety Data

• Hazardous Substances Data: 25877-73-0(Hazardous Substances Data)

Upstream product

• 4458-39-3 biphenyl-3,4-diamine 
• 63019-88-5 3-amino-4-(acetylamino)biphenyl 
• 4085-18-1 4-amino-3-nitrobiphenyl 
• 20691-72-9 4-iodo-2-nitroaniline 
• 98-80-6 phenylboronic acid 
• 206879-57-4 4-Fluoro-3-nitrobiphenyl 
• 364-73-8 4-Bromo-1-fluoro-2-nitrobenzene 
• 18355-04-9 6-bromo-1H-benzo[d][1,2,3]triazol-1-ol 

Downstream Products

• 860591-73-7 1-acetyl-5-phenyl-1H-benzotriazole 

Relevant articles and documents

Synthesis of Structurally Diverse Benzotriazoles via Rapid Diazotization and Intramolecular Cyclization of 1,2-Aryldiamines

An operationally simple method has been developed for the preparation of N-unsubstituted benzotriazoles by diazotization and intramolecular cyclization of a wide range of 1,2-aryldiamines under mild conditions, using a polymer-supported nitrite reagent and p-tosic acid. The functional group tolerance of this approach was further demonstrated with effective activation and cyclization of N-alkyl, -aryl, and -acyl ortho-aminoanilines leading to the synthesis of N1-substituted benzotriazoles. The synthetic utility of this one-pot heterocyclization process was exemplified with the preparation of a number of biologically and medicinally important benzotriazole scaffolds, including an α-amino acid analogue.

Mild and general access to diverse 1H-benzotriazoles via diboron-mediated N-OH deoxygenation and palladium-catalyzed C-C and C -N bond formation

Benzotriazoles are a highly important class of compounds with broad-ranging applications in such diverse areas as medicinal chemistry, as auxiliaries in organic synthesis, in metallurgical applications, in aircraft deicing and brake fluids, and as antifog agents in photography. Although there are numerous approaches to N-substituted benzotriazoles, the essentially one general method to N-unsubstituted benzotriazoles is via diazotization of ortho -phenylenediamines, which can be limited by the availability of suitable precursors. Other methods to N-unsubstitued benzotriazoles are quite specialized. Although reduction of 1-hydroxy-1 H-benzotriazoles is known, the reactions are not particularly convenient or broadly applicable. This presents a limitation for easy access to and availability of diverse benzotri-ACHTUNGTRENUNGazoles. Herein, we demonstrate a new, broadly applicable method to diverse 1H-benzotriazoles via a mild diboron reagent-mediated deoxygenation of 1-hydroxy-1H-benzotriazoles. We have also evaluated sequential deoxygenation and Pd-mediated C-C and C-N bond formation as a one-pot process for further diversification of the benzotriazole moiety. However, the results indicated that purification of the deoxygenation product prior to the Pd-mediated reaction is critical to the success of such reactions. The overall chemistry allows for facile access to a variety of new benzotriazoles. Along with the several examples presented, a discussion of the advantages of the approaches is described, as is also a possible mechanism for the deoxygenation process.