2,4,6-Triamino-l,3,5-trinitrobenzene

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. 

The reactions of hexanitrobenzene (55) and 2,3,4,5,6-pentanitroaniline (31) with ammonia have been used to synthesize the thermally stable explosive l,3,5-triamino-2,4,6-trinitrobenzene (TATB). Holmes and Fliirschiem have studied the reactions of 2,3,4,5,6-pentanitroaniline with nucleophiles. 

TATNB (l,3,5-Triamino-2,4,6-trinitrobenzene) TeNCbz (Tetranitrocarba zole) TeNB (1,3,5 Tetranitrobenzene) TNN (Trinitronaphthalene) Metal powder/ ox id a nt mixture (such as B/KNO3, Zr/KC104, etc) and Mg/Teflon... 

A single-point HF/6-31G calculation on l,3,5-triamino-2,4,6-trinitrobenzene, 282 basis functions this was said to require 2.6 h on a 90 MHz pentium machine Gaussian News, Summer 1995. This calculation on the Cj conformation, using a 650 MHz Pentium 111, took 13 and 46 min with two popular programs (Febmary 2000). 

Wang, P. S., and Wittbery, T. N., Surface characterization of l,3,5-triamino-2,4,6-trinitrobenzene by x-ray photoelectron spectroscopy and Fourier transform nuclear magnetic resonance, J. Mater. Sci., 24, 1533 (1989). 

Formal sequential addition of amino groups to 2,4,6-trinitroaniline gives 1,3-dianiino-2,4,6-trinitrobenzene (DATS, 56) and l,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. 

Table 1.2 Examples ofPBX compositions, where HMX is cyclotetramethylene-tetranitramine (Octogen), HNS is hexanitrostilbene, PETN is pentaerythritol tetranitrate, RDX is cyclotrimethylenetrinitramine Hexogen) and TATB is l,3,5-triamino-2,4,6-trinitrobenzene...

PDAD-MAC Poly(diallyldimethyl ammonium chloride) TATB l,3,5-Triamino-2,4,6- trinitrobenzene... 

TATB. TATB (2.16) is also known as l,3,5-triamino-2,4,6-trinitrobenzene (CeHsNsOe) and was first obtained in 1888 by Jackson and Wing. 

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