59635-31-3

Basic information

• Product Name: 2-(4-bromophenyl)-5-phenyl-2H-tetrazole
• Synonyms: 2-(4-bromophenyl)-5-phenyl-2H-tetrazole
• CAS NO: 59635-31-3
• Molecular Weight: 301.145
• Mol File: 59635-31-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-(4-bromophenyl)-5-phenyl-2H-tetrazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-bromophenyl)-5-phenyl-2H-tetrazole(59635-31-3)
• EPA Substance Registry System: 2-(4-bromophenyl)-5-phenyl-2H-tetrazole(59635-31-3)

Safety Data

• Hazardous Substances Data: 59635-31-3(Hazardous Substances Data)

Upstream product

• 622-37-7 Phenyl azide 
• 16917-43-4 benzaldehyde 4-bromophenylhydrazone 
• 1712-82-9 p-bromodibenzoyl peroxide 
• 18039-42-4 5-phenyl-2H-1,2,3,4-tetrazole 

Downstream Products

• 88235-87-4 N-(4-Bromphenyl)-C-phenylnitrilimin 
• 118795-00-9 2-(4-Bromo-phenyl)-3-methyl-5-phenyl-3,4-dihydro-2H-pyrazole-3-carboxylic acid methyl ester 
• 98321-11-0 C₁₃H₉BrN₂ 

Relevant articles and documents

Bu4NI-Catalyzed, Radical-Induced Regioselective N-Alkylations and Arylations of Tetrazoles Using Organic Peroxides/Peresters

Bu4NI-catalyzed regioselective N2-methylation, N2-Alkylation, and N2-Arylation of tetrazoles have been achieved using tert-butyl hydroperoxide (TBHP) as the methyl source, alkyl diacyl peroxides as the primary alkyl source, alkyl peresters as the secondary and tertiary alkyl sources, and aryl diacyl peroxides as the arylating source. These reactions proceed without pre-functionalization of tetrazole and in the absence of any metal catalysts. Here, peroxides serve the dual role of oxidants as well as alkylating or arylating agents. Based on DFT calculations, it was found that spin density, transition-state barriers (kinetic control), and thermodynamic stability of the products (thermodynamic control) play essential roles in the observed regioselectivity during N-Alkylation. This radical-mediated process is amenable to a broad range of substrates and provides products in moderate to good yields.

Hypervalent iodine in synthesis 87: The synthesis of 2,5-diaryl-2H- tetrazoles

In the presence of cuprous iodide and potassium carbonate, N-arylation of 5-aryl-2H-tetrazole with a diaryliodonium salt proceeds smoothly in DMF at room temperature to give 2, 5-diaryl-2H-tetrazoles in moderate to good yield.