3,5-diamino-2,4,6-trinitrotoluene

Haidour and Ramos (1996) analyzed the degradation products of 2,4,6-trinitrotoluene, 2,4-dinitrotoluene, and 2,6-dinitrotoluene by the bacterium Pseudomonas sp. clone A under aerobic conditions. Reduced 2,4,6-trinitrotoluene metabolites, which were not used as a nitrogen source by this bacterium, were 2-hydroxyamino-4,6-dinitrotoluene, 4-hydroxyamino-2,6-dinitrotoluene, and 2,4-diamino-6-nitrotoluene. 

Figure 14.6 Reduction pathway of 2,4,6-trinitrotoluene to aminodi-nitrotoluenes (ADNTs), diamino-nitrotoluenes (DANTs), and tri-aminotoluene (TAT).

In an ironic aside, it is noted that the most recently suggested new use for phosgene is to "make safe" thousands of tons of TNT (2,4,6-trinitrotoluene) from redundant weapons, no longer required now that the Cold War has ended. Treatment of the TNT with ammonium sulfide would reduce it to 2,4-diamino-6-nitrotoluene, which could then be treated with phosgene to give 2,4-diisocyanato-6-nitrotoluene (NDTI), a potentially valuable precursor for polyurethane manufacture [64d]. Thus, instead of potentially hazardous, and certainly wasteful, destruction of the TNT, the use of phosgene could convert it into a valuable industrial commodity. 

Dawel G et al., Structure of a laccase-mediated product of coupling of 2,4-diamino-6-nitrotoluene (2,4-DANT) to guaiacol, a model for coupling of 2,4,6-trinitrotoluene (TNT) metabolites to humic organic soil matrix, Appl. Environ. Microbiol., 63, 2560, 1997. 

Karamova NS et al., Compounds 2,4,6-trinitrotoluene and 2,4-diamino-6-nitrotoluene The absence of recA-dependent mutagenesis, Russ. J. Genet., 31, 528, 1995. 

Diamino-2,4,6-trinitrotoluene was made according lo the improved method of Palmer [69. ... 

Trinitrotoluene (TNT) and its biotransformation products (2,6-diamino-4-nitrotoluene, 2,4-diamino-6-nitrotoluene, 4-amino-2,6-dinitrotoluene, and 2-amino-4,6-dinitrotoluene) were baseline resolved on tandem Cig/cyanopropyl columns (A = 230nm) using a 60.5/25/14.5 water/methanol/THF mobile phase. Elution was complete in <20 min [182]. 

Redox reactions In order to mitigate the environmental hazard of 2,4,6-trinitrotoluene (TNT) a procedure was developed for its reduction. Treatment with Saccharomyces cervisiae (32 °C, 3-4 d) converted carbon-14-labeled TNT to a mixture of its four mono-and diamino- metabolites in a one-step procedure. 

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