Azoxytoluenes

Interactions may take place between metabolites at different levels of reduction. This may plausibly account for the dimerization of partially reduced intermediates to nitro-azoxytoluenes (Bayman and Radkar 1997), and the identification of azoxy componnds as biotransformation products of 2,4-dinitrotoluene by the fungus Mucrosporium sp. (Figure 9.49) (McCormick et al. 1978). 

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 utilizing 2,4-dinitrotoluene as a source of nitrogen. Two metabolites tentatively identified were 2-amino-4-nitrotoluene and 4-amino-2-nitrotoluene. Also, three azoxytoluenes were identified 4,4 -dinitro-2,2 -azoxytoluene, 2,2 -dinitro-4,4 -azoxytoluene, and 2,4 -dinitro-2, 4-azoxytoluene. 2-Amino-4-nitrotoluene and 4-amino-2-nitrotoluene were also identified as products of 2,4-dinitrotoluene metabolism by Clostridium acetobutylicum via the hydroxyl-aminonitrotoluene intermediates, namely 4-hydroxylamino-2-nitrotoluene and 2-hydroxylamino-4-nitrotoluene (Hughes et al., 1999). 

Dimethylurea, see Methyl isocyanate lYlV-Dimethylurea, see Aldicarb 2,2 -Dinitro-4,4 -azoxytoluene, see 2,4-Dinitrotoluene 2,4 -Dinitro-2, 4-azoxytoluene, see 2,4-Dinitrotoluene 4,4 -Dinitro-2,2 -azoxytoluene, see 2,4-Dinitrotoluene 6,6 -Dinitro-2,2 -azoxytoluene, see 2,4-Dinitrotoluene 4,4 -Dinitrobiphenyl, see Benzidine Dinitrocresols, see 2-Methylphenol iV-(2,6-Dinitro-3,4-dimethyl)phenyl acetamide, see... 

Gore and Wheeler [26] report the melting point of p-azoxytoluene as 68°C, citing Bamberger and Renauld [11] as reporting 69°C. This is in agreement with Lefort [31]. b Nematic-liquid transition 135°C. c Nematic-liquid transition 165°C. 

To a solution of 1 gm of sodium methoxide in 9 ml of methanol maintained at 42°-43°C is added 1 gm of trans-w-azoxytoluene. After a short stirring period, a white precipitate begins to separate. The solid is collected on a filter and recrystallized from toluene-ethanol, m.p. 190°-192°C yield not reported. 

N 12.38%. Five isomers are described in the literature 0,0 azoxytoluene or 2,2 - dimetbylazoxybenzene yel plates (from peer eth) or It yel lfts (from dil ale) mp 59-60°, explodes and chars on rapid heating (Ref 1) iso-o,o -azoxytoluene It yel long ndls (from petr eth), prisms (from benz) or little ndls (from methyl ale + w) mp 80-2° readily sol in common org solvs, petr eth or cold benz insol in w its solns are It yel in color (Ref 2) m,m -azoxytoluene or 3.3 -dimethylazoxytoluene It yel ndls (from eth) mp 37-9° readily sol in ale, eth, chlf, CSa, Iigroin or benz (Ref 3) p,p -azoxytoluene or 4,4 -dimetbylazoxytoluene pale yel ndls (from ale) or sulfur yel plates (from Iigroin) mp 69- 70a, readily sol in ale or eth (Ref 4) and w,w -azoxytoluene, C6H5 -CHa-fNaO) CHj QHs (Ref 5). The prepn and other props of these azoxytoluenes can be found in the refs indicated. Nitro or other derivs of azoxytoluene may be of interest as expl ingredients... 

Azido, CI4Hl3Ns O, and Diazido. C,4Hi2N,0, derivs of azoxytoluene were not found in Beil or in CA through 1956... 

In addition to the compds in Table 1, they obtained evidence for 2-hydroxylamino4,6-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-tri-nitrobenzyl alcohol. They confirmed that 2,2 6,6,-tetranitro4,4f azoxytoluene 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 bright 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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