Trinitroanilin

The phenomenon has also been observed in the AT-nitration of iV-methyl-2,4,6-trinitroaniline and the O-nitration of alcohols. ... 

Another circumstance which could change the most commonly observed characteristics of the two-stage process of substitution has already been mentioned it is that in which the step in which the proton is lost is retarded because of a low concentration of base. Such an effect has not been observed in aromatic nitration ( 6.2.2), but it is interesting to note that it occurs in A -nitration. The A -nitration of A -methyl-2,4,6-trinitroaniline does not show a deuterium isotope effect in dilute sulphuric acid but does so in more concentrated solutions (> 60 % sulphuric acid kjj/kjj = 4 8). ... 

The nitrosylsulfuric acid method is particularly suitable for the diazotization of di- and trinitroanilines and aminoanthraquinones. Such amines may be added directly to the nitrosylsulfuric acid, but it is preferable to run the appropriate amount of nitrosylsulfuric acid into a solution of the amine in 96% sulfuric acid. In general, these diazotizations can be carried out at room temperature. The end-point is determined in the usual manner with iodide paper, but only after first diluting a few drops with ice. On completion, the whole is diluted with ice. The test with iodide paper fails in the case of polynitrodiazonium salts. 

N-methyl-N,2,4-trinitroaniline, nitration of, 12 microscopic reversibility, and protodeiodina-tion, 356... 

Fig. 1.11 Dissociation ranges of colour indicators for determination of the acidity function H0 in H2S04-H20 mixtures (1) p-nitroaniline, (2) o-nitroaniline, (3) p-chloro-o-nitroaniline, (4) p-nitrodiphenylamine, (5) 2,4-dichloro-6-nitroaniline, (6) p-nitroazobenzene, (7) 2,6-dinitro-4-methylaniline, (8) benzalacetophenone, (9) 6-bromo-2,4-dinitroaniline, (10) anthraquinone, (11) 2,4,6-trinitroaniline. (According to L. P. Hammett and A. J. Deyrup)...

This salt of the ac/-o-iminoquinonoid form of 2,4,6-trinitroaniline explodes violently at 110°C. 

Das Dinitrochlorbenzol ist ein Zwischenprodukt fur viele Synthesen (- Hexanitrodiphenylamin, Trinitrochlorbenzol, Trinitroanilin, Trinitro-benzol usw.). 

In general the method is not as useful for the preparation of arylamines as for aliphatic amines. But the method becomes of preparative interest when the nuclear halogenated compound contains in addition some electron withdrawing substituents e.g., -N02, -CN etc. in ortho and para positions. Thus, 2, 4, 6 trinitroaniline (picramide) is readily prepared by the action of aqueous ammonia on... 

Trinitroaniline (TNA) has but one isomer (the long known 2,4,6-species) with a reported enthalpy of formation. Its positive DSE, and hence relative stabilization, is due to hydrogen... 

Formal sequential addition of amino groups to 2,4,6-trinitroaniline gives 1,3-diamino-2,4,6-trinitrobenzene (DATB, 56) and 1,3,5-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. 

The same displacement occurs in the hydrolysis of picrylimidazole238 (103). 103 reacts with n-butylamine in water239 to yield picric acid (from the reaction with water) and N-n-butyl-2,4,6-trinitroaniline. The dependence of k0bs values (s 1 moP1 dm3) on pH values indicates the presence (and importance) of equilibrium 27 on the reaction pathway of the... 

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