Aliphatic Versus Aromatic Nucleophilic Attack of NH₃ on Trialkoxy-trinitrobenzenes in the Preparation of TATB

1,3,5-Trimethoxy-2,4,6-trinitrobenzene, 1,3,5-triethoxy-2,4,6-trinitrobenzene, and 1,3-dimethoxy-2,4,6-trinitro-5-propoxybenzene were used in a comparative amination study to evaluate the effect that alkyl ether chain length has on directing the nucleophile in the preparation of 1,3,5-triamino-2,4,6-trinitrobenzene. The results indicated that in the presence of excess ammonia, the aromatic propyl ether carbon is more susceptible to nucleophilic attack than the aromatic methyl ether carbons. Amination of 1,3,5-triethoxy-2,4,6-trinitrobenzene yielded the purest 1,3,5-triamino-2,4,6-trinitrobenzene. The implications of these results on the nucleophilic amination reaction are discussed.