2-amino-4,6-dinitrotoluene

Wang, C. J., Thiele, S., and Bollag, J. M., 2002, Interaction of 2,4,6-trinitrotoluene (TNT) and 4-amino-2,6-dinitrotoluene with humic monomers in the presence of oxidative enzymes. Arch. Environ. Contam. Toxicol. 42 1-8. 

Amino-4,6-dinitrotoluene, see 2.4.6-Trinitrotoluene 4-Amino-2,6-dinitrotoluene, see 2.4.6-Trinitrotoluene 4-Aminodiphenylamine, see Aniline... 

Solid-phase microextraction (SPME) for preconcentration, followed by GC/ Ion Trap MS, was used for trace analysis of explosives and their metabolites in seawater [9]. NICI was used with methane as reagent gas. Compounds of interest included RDX, TNT and two of its metabofrtes 2-amino-4,6-dinitrotoluene (2ADNT) and 4-amino-2,6-dinitrotoluene (4ADNT). Although the instrument sensitivity was in low-ppb range, the detection limits for SPME with GC/ITMS... 

More complex explosives incorporating amino groups have been prepared from the reaction of polynitroarylene halides with amine nucleophiles. Agrawal and co-workers have synthesized PADNT (107) from the reaction of 4-amino-2,6-dinitrotoluene (46) with picryl chloride (87) in methanol 4-amino-2,6-dinitrotoluene is synthesized from the reduction of... 

The synthesis of TATB (14) from the reaction of 2,3,4,5,6-pentanitroaniline (31) with ammonia has been reported. " In one route, 2,3,4,5,6-pentanitroaniline (31) is synthesized from the nitration of 3,5-dinitroaniline (30) " the latter is obtained from the selective reduction of TNB ° or via a Schmidt reaction with 3,5-dinitrobenzoic acid. Another route to 2,3,4,5,6-pentanitroaniline (31) involves the selective reduction of TNT (1) with hydrogen sulfide in ammonia followed by nitration of the resulting 4-amino-2,6-dinitrotoluene (46), during which the methyl group is lost by oxidation-decarboxylation. 

During World War II, copious quantities of ordnance were lost into the harbor at Halifax, Nova Scotia. Decades later, these UUXO now present a significant environmental contamination problem. Studies conducted on this ordnance by Sandia National Laboratories [1] suggest that there may be sufficient concentrations of explosive chemical signature compounds emanating from UUXO to enable detection with chemical sensors. Some UUXO in Halifax Harbor have been shown to produce parts-per-billion levels of explosives in the water near the ordnance. In addition to the parent explosive compound (TNT), other explosive-related compounds such as 2,4-dinitrotoluene (2,4-DNT) were detected, as were degradation products of TNT such as 4-amino-2,6-dinitrotoluene (4-ADNT), and... 

C. bifermentam strain CYS-1 was also isolated from our anaerobic bioreactor. Shin Crawford (1995) examined the ability of CYS-1 to degrade TNT cometabolically in various defined media. This strain could overcome the toxicity of and degrade >150 ppm TNT in liquid media supplemented with a rich cosubstrate such as yeast extract or trypticase soy, given an appropriate inoculum ( 107 CFU/ml). Furthermore, it was found that CYS-1 could degrade TNT which contaminated a sandy loam soil. The degradation of TNT proceeded through the transient intermediates 4-amino-2,6-dinitrotoluene and 2,4-diamino-6-nitrotoluene. 

Amino-2,6-dinitrotohiene can be made by treating TNT in dioxane with anun sulfide (Refs 4 98). A 37% yield of material of 99% purity was obtained (Ref 4). Reaction of TNT with ethyl ale hydrogen sulfide containing a small quantity of ammonia gives a mixt comprising 22% unreacted TNT, 22% 4-amino-2,6-dinitrotoluene, 4% 2-amino-4,6-dinitrotoluene, 44% 4-hydroxylamino-2,6-dinitrotoluene and 8% 2-hydroxylamino-4,6-dinitrotoluene (Ref 4). 

Amino -2,6 -dinitrotoluene Is of interest as the intermediate for one procedure for preparing the thennally-stable, insensitive expl 2,4,6-triaminotrinitrobenzene (TATB) (Ref 119). Tri-nitrophloroglucinol (TNPG, see Vol 8, P248-R), the metallic salts of which have been considered as expl initiators, can also be made from It (Ref y 4). The reactions are ... 

Stock solutions (1000 mg/L in acetonitrile) of 2,4,6-trinitrotoluene (TNT), 1,3,5-trinitrobenzene (TNB), 2,4-dinitrotoluene (2,4-DNT), and 4-amino-2,6-dinitrotoluene (4-Am-2,6-DNT) (Supelco). Sodium dodecyl sulfate (SDS) and sodium borate 10-hydrate. Standard solutions of the various explosives should be prepared daily (using the proper safety precautions) in an SDS-containing electrophoresis buffer. Platinum and silver wires, 0.1mm diameter. 

In the non-target analysis of this sample, carried out by LC-NMR and LC-MS, TNT-typical biodegradation products such as 2-amino-4,6-dinitro-toluene and 4-amino-2,6-dinitrotoluene were detected, although smaller quantities of 2-amino-4,6-dinitrobenzoic acid, trinitrobenzene and 2,2/6,6/-tet-ranitro-4,4/-azoxytoluene could also be identified. The NMR chromatogram further reveals that the soil was also contaminated by PAHs. Several late-eluting compounds could be identified as PAHs. 

Summary A-NPNT is prepared in a three step process starting with the well know high explosive, TNT. TNT is reduced to 4-amino-2,6-dinitrotoluene with hydrogen sulfide gas and ammonia solution. The reduction product is then converted to 4-... 

Dissolve 100 grams of 2,4,6-trinitrotoluene into 200 milliliters of p-dioxane, and then place the mixture into a cold-water bath. Then stir the mixture, and add 2 milliliters of 28 - 30% ammonium solution. Then bubble 46 grams of hydrogen sulfide gas into the mixture over a 2-hour period while keeping the reaction temperature at 20 Celsius by means of the cold-water bath, and stir the reaction mixture continuously during the addition. After the addition of the hydrogen sulfide gas, filter off the precipitated sulfur, and then add the filtered reaction mixture to 1000 milliliters of ice water. After which, filter off the yellow precipitated solid, and then wash the solid with 400 milliliters of water. Then vacuum dry or air-dry the solid. The result is a mixture of the desired 4-amino-2,6-dinitrotoluene (61%), and the by-product, 4-hydroxylamino-2,6-dinitrotoluene (39%). 

TNT is readily absorbed through skin, especially when skin is moist. It is excreted in urine more than in feces some is found in bile. The major biotransformation reaction is nitroreduction and, to a lesser extent, oxidation. The main metabolite formed by nitroreduction seems to be 4-amino-2,6-dinitrotoluene (4-ADNT). Other metabolites include 2-amino-4,6-dinitrotoluene (2-ADNT), 2,4-diamino-6-nitrotoluene, and 2,6-diamino-4-nitrotoluene. The metabolites are excreted in the urine as glucuronide conjugates and in the free form. Ring oxidation products of TNT such as trinitrobenzylalcohol, trinitrobenzoic acid, and simultaneous oxidation and reduction metabolites such as 2,6-dinitro-4-amino-benzylalcohol and 2,6-dinitro-4-amino-m-cresol are of less importance. Untransformed TNT is also excreted in the urine. ADNT and TNT concentrations were found in workers in explosives factories. 4-ADNT excretion was reported to be complete within 3M days after exposure. However, another study reported detectable urine concentration of ADNT in explosives workers even after 17 days away from the workplace. 

Various modern products may serve as sources for trace amounts of PAA. The origins, known hazards, release restrictions and environmental fate of PAA derived from azo dyes have been reviewed2. The metabolism of nitroarenes is closely linked to that of aromatic amines, as shown in a simplified way in equation 369. Gloeophyllum trabeum cultures spiked with TNT show formation of nitroaromatic amines such as 2-ami no-4,6-dinitrotoluene, 4-amino-2,6-dinitrotoluene and 2,4-diamino-6-nitrotoluene. Also, autoxi-dation of the methyl group of TNT or its metabolites may take part in the degradation process, as shown by the presence of Schiff bases and oligomeric and polymeric species detection and determination of the analytes after LLE and concentration were by HPLC-UVD or GC-MS70. 

Peterson MM et al., TNT and 4-amino-2,6-dinitrotoluene influence on germination and early seedling development of tall fescue, Environ. Pollut., 93, 57, 1996. 

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. 

Trinitrotoluene (TNT) is the most commonly used energetic compound and found in the soils at U.S. Army installations [16,17], Military grades of TNT contain up to 8% DNTs (2,4-dinitrotoluene and 2,6-dinitrotoluene) as manufacturing impurities, and TNT is often degraded to DNT in hydric soils (i.e., wet anaerobic environments) [18,19], Other compounds are also generated when TNT is degraded (e.g., 2-amino-4,6-dinitrotoluene [2-ADNT], 4-amino-2,6-dinitrotoluene [4-ADNT], 1,3,5-trinitrobenzene [TNB], and others). Contamination from TNT, DNTs, and their environmental breakdown products is known to persist in soil for years [20],... 

Amino-2,6-dinitrotoluene is of interest as the intermediate for one procedure for preparing the thermally-stable, insensitive expl 2,4,6-... 

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