Picramid Trinitroanilin

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... 

Solutions of sodium or potassium nitrates in concentrated sulfuric acid can be used as a substitute for anhydrous mixed acid." 2,4,6-Trinitroaniline (picramide) has been synthesized via the addition of a solution of potassium nitrate in concentrated sulfuric acid to a solution of either o- or p-acetanilide in oleum. ... 

The presence of three nitro groups on the aromatic ring of picryl chloride makes the chloro group extremely reactive towards nucleophiles. Picryl chloride (87) is hydrolyzed to picric acid (4) in the presence of hot water or aqueous sodium hydroxide. Aminolysis of picryl chloride in the presence of primary and secondary amines is complete in minutes at room temperature. Picryl chloride is therefore a very useful starting material for the synthesis of a range of other picryl derivatives. The reaction of picryl chloride (87) with ammonia can be used to synthesize 2,4,6-trinitroaniline (53) (picramide). Treatment of picryl chloride with alcohols under reflux forms picric acid and the alkyl chloride of the corresponding alcohol, whereas the same reaction in the presence of alkali metal hydroxides, or the alkoxide anion of... 

Picryl chloride (87) reacts with hydroxylamine hydrochloride to yield 2,4,6-trinitroaniline (53) (picramide) and not the expected At-hydroxy-2,4,6-trinitroaniline. In contrast, the same reaction in the presence of sodium ethoxide is reported to yield 4,6-dinitrobenzofuroxan (94) via substitution of the halogen by hydroxylamine, followed by an internal redox reaction between the hydroxyamino group and one of the adjacent o-nitro groups. ... 

Other explosives, such as 2,4,6-trinitroanisole (7),33b.226 2,4,6-trinitroaniline (picramide), and tetryl (101), ° are conveniently prepared from the nitration of the corresponding 2,4-dinitro derivatives, which in turn, are prepared from the reaction of 2,4-dinitrochlorobenzene with the appropriate nucleophile. 

As a rule explosives were listed and described under their parent compounds arranged in alphabetical order, as for example 2,4,6-Trinitroaniline or Picramide is described under ANILINE in Vol I of Encycl. Most of the metallic salts are described under the names of their anions as, for example, Lead Azide (LA) is described under AZIDES, Mercuric Fulminate (MF), under FULMINATES, whereas some salts are described under the names of their cations- as for example Ammonium Nitrate (AN) is described under AMMONIUM in Vol 1... 

CA 42, 874 (1948) N-Cyclohexyl 2,4,6,-Trinitroaniline N-Cydo-hexyl Picramide or 2,4,6-Trinitro 1-cyclohexyla-minobenzene, C6H2(N02)3NH.C6Hu mw 310.26,... 

Picramic Acid. See 2,6-Dinitro-2-aminophenol under Aminophenols A241-R Picramide. See 2,4,6-Trinitroaniline A40S R to A411-L... 

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