Research on the VNS reaction of 1-amino-1, 2, 3-triazole

1-amino-1, 2, 3-triazole was used as a new amino source to prepare TATB through vicarious necleophilic susbstitution (VNS) reaction of trinitrobenzene (TNB) with 90.6% yield and more than 99% purity (HPLC). Some key reaction parameters were investigated in term of isolated yield of TATB. Under the optimized reaction conditions, the effect of nitro groups of the aromatic ring on the yield of the VNS reaction was analyzed. 1, 3-Diamino-2, 4, 6-trinitro-5-methyl-benzene (DATNT), 1, 3-diamino-2, 4-dinitrobenzene (DADNB), and p-nitroaniline were obtained in isolated yield of 40.5%, 54.5%, and 38.4%, respectively, by taking TNT, nitrobenzene and m-dinitrobenzene as substrate. A reaction mechanism of which 1-amino-1, 2, 3-triazole was used as amination reagent for VNS amination reaction was proposed to explain the formation of TATB under such a basic condition.