21268-85-9

Upstream product

• 186581-53-3 diazomethane 
• 23408-16-4 3,5-dinitro-2-aminophenol 
• 13661-34-2 1,2-dimethoxy-3,5-dinitrobenzene 
• 6295-94-9 N-tosyl-2-anisidine 
• 7539-25-5 1-methoxy-2,3,5-trinitrobenzene 
• 77-78-1 dimethyl sulfate 
• 5327-44-6 3,5-dinitroanisole 
• 97-52-9 2-methoxy-4-nitrophenylamine 
• 4097-63-6 2-methoxy-4,6-dinitrophenol 
• 41669-93-6 2-chloro-3,5-dinitro-anisole 
• 729603-02-5 2-benzenesulfonyl-1-methoxy-3,5-dinitro-benzene 
• 861785-89-9 1-methoxy-3,5-dinitro-2-phenoxy-benzene 

Downstream Products

• 64381-88-0 2-amino-3-methoxy-5-nitroaniline 
• 116611-89-3 7-amino-5-methoxy-2,3-diphenylquinoxaline 
• 102872-07-1 6-amino-4-methoxy-2-methyl-1H-benzimidazole 
• 102554-55-2 5-hydroxy-2,3-diphenylquinoxaline 
• 32387-89-6 5-methoxy-2,3-diphenyl-quinoxaline 
• 116588-13-7 <5-(2,3-diphenyl)-quinoxalyl> dimethyl phosphate 
• 860367-75-5 7-amino-5-hydroxy-1H-quinoxalin-2-one 
• 103752-67-6 acetic acid-(2-methoxy-4,6-dinitro-anilide) 

Relevant academic research and scientific papers

An efficient one-pot synthesis of aminobenzimidazoles

An efficient one-pot procedure for the preparation of aminobenzimidazoles from dinitroaniline derivatives is described. The process helps to avoid the troublesome acetonitrile-mediated reductive ethylation reaction.

Direct amination of 1-substituted 3,5-dinitrobenzenes by 1,1,1-trimethylhydrazinium iodide

The amination of 1-X-3,5-dinitrobenzenes via the vicarious nucleophilic substitution of hydrogen (VNS) with 1,1,1-trimethylhydrazinium iodide (TMHI) in the presence of t-BuOK or NaOMe in DMSO was studied. It was observed (when X = OMe, OCH2CF3, OCH2CF2CF2H, OPh) that the amination occurs regioselectively (ratio of ortho/para-isomers is ～9:1) and with high yield. For X = SPh or SCH2Ph, the reaction proceeded with a low yield (less than 20%), with a ratio of ortho/para-isomers ≈1:1. For X = PhSO2 and 2 equiv of TMHI, a double amination occurs and 2,4-diamino-3,5- dinitro-1-phenylsulfonylbenzene predominates in the mixture of isomers. Under the same conditions, 1,3,5-trinitrobenzene undergoes a double amination to yield 2,4-diamino-1,3,5-trinitrobenzene. A proposed mechanism for this reaction is discussed.