Chinese Journal of Applied Chemistry

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Synthesis of 3,5-Dichloro-2,4,6-trinitrobenzenamine and Its Derivatives

HOU Kehui, LIU Zuliang*   

  1. (School of Chemical Engineering,Nanjing University of Science and Technology,Nanjing 21009,China)
  • Received:2013-01-21 Revised:2013-04-12 Published:2013-11-10 Online:2013-11-10

Abstract: Two synthetic methods have been developed for the synthesis of 3,5-dichloro-2,4,6-trinitrobenzenamine. In the first process, 3,5-dichlorobenzenamine was selected as precursor, followed by N-protection, nitration, and hydrolysis. In another process, 1,3,5-trichloro-2,4,6-tri-nitrobenzene(TCTNB) reacted with 2-amino-2-methylpropane and then trifluoroacetic acid to deprotect. The condensation between 3,5-dichloro-2,4,6-trinitrobenzenamine and methylamine gave 3,5-dimethylamino-2,4,6-trinitrobenzenamine in 85% yield which can be converted to the nitrate of 3,5-dimethylnitramino-2,4,6-trinitrobenzenamine in 70% yield. The structure of the product was confirmed by 1H NMR, MS, IR and elemental analysis. The results of selective of TCTNB under different conditions were discussed. The optimized conditions are:n(TCTNB)∶n(t-butylamine)=1∶2, CuO as catalyst, KHCO3 as base.

Key words: synthesis, dichloro-trinitrobenzenamine, dimethylamino-trinitrobenzenamine, dimethylnitramino-trinitrobenzenamine nitrate, enegetic material

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