58808-54-1

Upstream product

• 6333-15-9 4,4'-dinitrobenzanilide 

Downstream Products

• 120191-18-6 N,N-dimethyl-4-nitro-N'-(4-nitro-phenyl)-benzamidine 
• 84901-05-3 2-(4-Nitro-phenyl)-5,7-diphenyl-[1,3,4]thiadiazolo[3,2-a]pyridin-4-ylium; chloride 
• 100-01-6 4-nitro-aniline 
• 113934-58-0 N-(p-nitrophenyl)-p'-nitrobenzimidic ester of 3,5,7-tribromotropolone 
• 99137-15-2 1,5-bis(4-nitrophenyl)tetrazole 
• 62718-52-9 N,N-diethyl-4-nitro-N'-(4-nitro-phenyl)-benzamidine 
• 62718-40-5 1-[4-nitro-N-(4-nitro-phenyl)-benzimidoyl]-piperidine 

Relevant academic research and scientific papers

Preparation of 1,5-disubstituted tetrazoles under phase-transfer conditions

Imidoyl chlorides, obtained by common methods from a wide range of aromatic mono- and diamides, are smoothly converted to the corresponding tetrazoles in high yields by treatment with NaN3 under phase-transfer conditions.

Intramolecular Reaction Between Nitro and Carbodi-imide Groups; A New Synthesis of 2-Arylbenzotriazoles

1-(2-Nitrophenyl)-5-phenyltetrazole (5b) decomposes when heated to give nitrogen, carbon dioxide, and 2-phenylbenzotriazole (6) in high yield.This new molecular rearrangement proceeds via 2-nitrophenyl(phenyl)carbodi-imide (8).Other precursors of this carbodi-imide, i.e. oxadiazolone (10), oxadiazolethione (11), oxathiadiazole 2-oxide (12), and the aminimide (16), and carbodi-imide itself, all give 2-phenylbenzotriazole (6) on thermolysis, the last three in high yield.This reaction is general for diarylcarbodi-imides with an ortho nitro group, and their precursors, and it provides a useful new route to 2-arylbenzotriazoles.A sequence of electrocyclic ring closing and opening reactions (Scheme 5) is proposed as the mechanism of this process.The key intermediate, 2-phenyl-1,2,4-benzotriazin-3-one 1-oxide (19) has been isolated from a careful thermolysis of (12) in toluene; in solution it is in reversible equlibrium with the ring-opened form (20).This new nitro-carbodi-imide group interaction has been extended to the more stable nitrobiphenyl(phenyl)carbodi-imide (25) and nitronaphthyl(phenyl)carbodi-imide (24) which, on flash vacuum pyrolysis, give benzimidazophenanthridine (29) and benzindazole 1-oxide (32) respectively, in new rearrangements.