2,4-diamino-1,3,5-trinitrobenzene:

Formal sequential addition of amino groups to 2,4,6-trinitroaniline gives 1,3-diamino-2,4,6-trinitrobenzene (DATB, 56) and 1,3,5-triamino-2,4,6-trinitrobenzene (TATB, 57). TATB is more stable than expected from the additivity calculation. The ability to have hydrogen bonding with three amino groups both intra- and inter-molecularly in the crystal stabilizes the molecule. The molecule that results is thermally stable and used as an explosive in situations where a very insensitive explosive is needed. 

Interest in polynitroarylenes has resumed over the past few decades as the demand for thermally stable explosives with a low sensitivity to impact has increased. This is mainly due to advances in military weapons technology but also for thermally demanding commercial applications i.e. oil well exploration, space programmes etc. Explosives like 1,3-diamino-2,4,6-trinitrobenzene (DATB) (13), l,3,5-triamino-2,4,6-trinitrobenzene (TATB) (14), 3,3 -diamino-2,2, 4,4, 6,6 -hexanitrobiphenyl (DIPAM) (15), 2,2, 4,4, 6,6 -hexanitrostilbene(HNS, VOD 7120 m/s, = 1.70 g/cm ) (16) and A,A -bis(l,2,4-triazol-3-yl)-4,4 -diamino-2,2, 3,3, 5,5, 6,6 -octanitroazobenzene (BTDAONAB) (17) fall into this class. TATB is the benchmark for thermal and impact insensitive explosives and finds wide use for military, space and nuclear applications. 

Watanabe T, Ishihara N, Ikeda M. 1976. Toxicity of and biological monitoring for 1,3-diamino-2,4,6-trinitrobenzene and other nitro-amino derivatives of benzene and chlorobenzene. Int Arch Occup Environ Health 37 157-168. 

Diamino-2,4,6-trinitrobenzene 5-Carboxy-l,3-diamino-2,4,6-trinitrobenzene 1,1- Dichloro-2-propanone, 1,1 -Dichloro acetone 5,7-Dintiro-5,7-diaza-l,3-dioxabicyclooctane-2-one Diazodinitrophenol... 

The effect on detonation transfer of the parameters shown in Fig Ex22 were reviewed for the donor and acceptor expls RDX, HNS-1 (2,4,6,2/,4/,6/-Hexanitrostilbene of 3 microns particle size) HNS-11 (Same as HNS-1, except of 200-300 microns particle size), DATB (1,3-Diamino-2,4,6-trinitrobenzene), and TATB (1,3,5-Triamino-2,4,6-trinitrobenzene) with a wide cross-section of sensitivities. Eash of these parameters has been individually qualified and explained on both the theoretical level and the impact on practical hardware design. The experimental study is described in Ref 2 Refs 1) M.L.Schimmel, "Quantitative Understanding of Explosive Stimulus Transfer... 

Preliminary results in the validation of a novel short term test. Mutat. Res., 46, 305-310 Watanabe, T., Ishihara, N. Ikeda, M. (1976) Toxicity of and biological monitoring for 1,3-diamino-2,4,6-trinitrobenzene and other nitro-amino derivatives of benzene and chlorobenzene. Int Arch, occup. environ. Health, 37, 157-168 Yoshimi, N., Sugie, S., Iwata, H., Niwa, K., Mori, H., Hashida, C. Shimizu, H. (1988) The genotoxicity of a variety of aniline derivatives in a DNA repair test with primary cultured rat hepatocytes. Mutat. Res., 206, 183-191... 

Prepare a mixture by adding 2.7 grams of 5-cyano-1,3-diamino-2,4,6-trinitrobenzene (prepared in step 2), and 60 milliliters of 98% sulfuric acid into 30 milliliters of water. Then heat the mixture to 100 Celsius for 90 minutes. After 90 minutes, remove the heat source and allow the mixture to cool to room temperature. Afterwards, pour the mixture into 500 milliliters of ice water. Then filter-off the precipitated product, wash with 200 milliliters of water 2 times, and then vacuum dry or air-dry. The yield will be 2.6 grams of crude 5-carboxy-l,3-diamino-2,4,6-trinitrobenzene. Then reciystallize this cmde product from 300 milliliters of acetonitrile. After reciystallization, wash the product with 200 milliliters of cold water, and then vacuum dry or air-dry the product. The dry product will be in the form of yellow needles with a melting point of 240 Celsius (with decomposition). 

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