3717-99-5

Upstream product

• 4760-34-3 N-methyl-1,2-phenylenediamine 
• 552-89-6 2-nitro-benzaldehyde 
• 88-73-3 2-Chloronitrobenzene 
• 612-28-2 2-nitro-N-methylaniline 
• 3717-98-4 N-methyl-N'-(2-nitro-benzylidene)-o-phenylenediamine 

Downstream Products

• 60418-17-9 2-(2-azidophenyl)-1-methylbenzimidazole 
• 29528-19-6 2-(1-methyl-1H-benzo[d]imidazol-2-yl)aniline 
• 60418-14-6 1-methyl-2-(2-nitrophenyl)-1H-benzo[d]imidazole 

Relevant academic research and scientific papers

In Situ Generation and Synthetic Application of 2-Phenylbenzimidazoline to the Selective Reduction of Carbon-Carbon Double Bonds of Electron-Deficient Olefins

2-Phenylbenzimidazoline (PBI) as a mild, selective, and convenient reducing agent was efficiently generated in situ from o-phenylenediamine and benzaldehyde in alcohols.A generally applicable method for the selective reduction of carbon-carbon double bonds of a variety of electron-deficient olefins with an alcoholic solution of PBI is described.The reduction of α,β-unsaturated ketones to the corresponding saturated ketones could also be accomplished (but, less effectively) with PBI with the aid of a Lewis-acid catalyst. 1-Methyl-2-(o-nitrophenyl)benzimidazoline prepared and isolated by the reaction of o-nitrobenzaldehyde with N-methyl-o-phenylenediamine reduced benzylidenemalononitrile to give benzylmalononitrile and 1-methyl-2-(o-nitrophenyl)benzimidazoline in high yields.This shows the validity of PBI to be the actual reducing species in the present reduction system.From a mechanistic study, the present reductions could be interpreted in terms of a mechanism involving a synchronous transport of a pair of hydrogens or a sequential transfer of a hydride and a proton from PBI to the olefins.

Competitive Cyclisations of Singlet and Triplet Nitrenes. Part 9. 2-(2-Nitrophenyl)-benzothiazoles and -benzimidazoles

2-(2-Nitrophenyl)benzothiazole, produced by deoxygenation of the corresponding nitro-compound or by thermolysis or photolysis of the related azide, gives indazolobenzothiazole by attack on the benzothiazole nitrogen.Similar attack of the nitrene in 2-(2-nitrophenyl)benzimidazoles gives benzimidazoindazoles in good yield.However, with an appropriate 1-substituent in the benzimidazole (e.g.Me or CHMe2) the nitrene in its triplet state (generated by acetophenone-sensitised photolysis or by thermolysis of the azide bearing a 4-dimethylamino-group) preferentially attacks this substituent giving benzimidazoquinazolines.