2,4,5,6-Tetranitro-3- -toluene

It exists as cis-, crysts (from petr eth), mp 47° and trans-, pltlts (from MeOH) or ndls (from acetic acid can be prepd from (i)cis or( )trans 1,2-diphenylcycIopenta-none-(3) or -(4) by heating with Zn amalgam aq HC1 in toluene (Refs 1 4) x,x,x,x Tetranitro-l,2-diphenylcyclopentane,... 

Steevens JA et al., Toxicity of the explosives 2,4,6-trinitro toluene, hexahydro-1,3,5-trinitro-l,3,5-triazine, and octahydro-l,3,5,7-tetranitro-l,3,5,7-tetrazocine in sediments to Chironomus tentans and Hyalella azteca Low-dose hormesis and high-dose mortality, Environ. Toxicol. Chem., 21, 1475, 2002. 

Primary nitroaromatics are TNT the environmental breakdown products, including 1,3,5-trinitrobenzene (TNB), 1,3-dinitrobenzene (DNB), 2,4-and 2,6-dinitro-toluene (DNTs) and the primary reduction products 2-amino 4,6-dinitrotoluene and 4-amino 2,6-dinitrotoluene (ADNTs). Nitramines include RDX and octahydro-l,3,5,7-tetranitro-l,3,5,7-tetrazocine (HMX). Additional energetic compounds discussed in this chapter include nitroglycerin, white phosphorus, and ammonium perchlorate. Other energetic compounds are not discussed due to a lack of information regarding toxicity to wildlife species. 

MC found primarily at impact areas and tiring lines of U.S. military testing and training ranges often consist of mixtures of residues from several MC. These may include the nitroaromatic explosive compounds 2,4,6-trinitrotoluene (TNT), 2,4- and 2,6-dinitro-toluene (DNT), and trinitrophenylmethylnitramine (tetryl) nitrate esters such as nitrocellulose (NC), pentaerythritol tetranitrate (PETN), and nitroglycerin (NG) and the nitramine compounds, hexahydro-l,3,5-trinitro-l,3,5-triazine (RDX) and octahydro-l,3,5,7-tetranitro-l,3,5,7-tetrazocine (HMX). Most of these MC have been in use for decades, either as primary or secondary explosives or in propellant compositions. 

In addition to the compds in Table 1, they obtained evidence for 2-hydroxylaraino4,6-dinitro-toluene, 2,4-diamino-6-nitrotoluene, 2,6-diamino-4-nitrotoluene, 2,4,6-trinitrobenzoic acid and (with considerable lack of confidence) 2,4,6-trinitrobenzyl alcohol. They confirmed that Ip , 6,6 -tetranitro-4,4 -azoxytoluerre is not a constituent of fresh urine, but may form from 4-hydroxylamino-2,6-dinitrotoluene when the urine is allowed to stand or during isolation procedures. They saw almost no unmetabolized TNT in urine. The urine of orally dosed rats and mice had a br t red color, but not that of dogs and rabbits. The radioactivity of labeled TNT was mainly excreted, but some ended up distributed in various organs... 

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