Trinitroanisol

A careful study of the reaction of 2 4 6 trinitroanisole with sodium methoxide revealed that two different Meisenheimer complexes were present Suggest reasonable structures for these two complexes... 

Trinitroanisole [606-35-9] M 243.1, m 68". Crystd from EtOH or MeOH. Dried under vac. 

Note According to Brady and Horton (Ref 6), TNPht forms an unstable addition compd with 2,4,6-Trinitroanisole (TNAns) consisting of 2 moles of TNPht and 3 moles of TNAns. The mp of this compd is about 40°... 

It was prepd in 1884 by Nolting and Collin (Ref 2) from ethyl- or methyl-esters of Styphnic Acid and ale ammonia. Blanksma (Ref 3) prepd it from 3-chlor-2,4,6-trinitroanisole (or 3-chlbr-2,4,6-trinit,rophetietole) and ale ammonia, Kbrner and Contardi ( Ref 4) from 2,4-dibrom- (or dichlor)- 3,5-trinitrobenzene and ale ammonia, and Fliirscheim (Ref 5) from tetranitro-aniline and ammonia... 

The compound is produced from interaction of trinitroanisole and sodium methoxide and explodes with great violence on heating in a free flame. It should probably be formulated as shown, a dimethyl acetal of the aci-p-quinonoid form of picric acid. 

A mixture of ammonium nitrate and 2,4,6-trinitroanisole, prepared as an explosive by mixing the hot components, ignited spontaneously and later exploded violently. 

Trimethylpyridine Trimethylsilanol Trimethylstibine Trimethylsuccinic anhydride Trimethylthiacyclopropane Trimethyltin bromide 2.4.6- Trinitroanisole 9.53... 

Trinitroanisol ist nicht loslich in Wasser, loslich in heiliem Alkohol und Ether. Es ist giftig. 

Trinitroanisol wird aus Dinitrochlorbenzol durch Behandeln mit Methyl-alkohol und Alkali und Weiternitrierung des so gewonnenen Dini-troanisols hergestellt. Umkristallisiert aus Methylalkohol erhalt man das reine, schwachgelb gefarbte Produkt. 

SjvAr reactions of nitroaromatics such as l-chloro-2,4-dinitrobenzene and 2,4,6-trinitroanisole with amines are accelerated in micelles or microemulsions49. As with anionic nucleophiles, the rate enhancement is mainly the effect of a high local concentration of both reactants18,31. 

Phenol ethers, like the parent phenols, are reactive substrates. Phenol ethers like anisole and phenetole are readily nitrated to their picryl ethers, 2,4,6-trinitroanisole and 2,4,6-trinitrophenetole respectively, on treatment with mixed acid composed of concentrated nitric and sulfuric acids at 0 °C. Such reactions are vigorous, prone to oxidative side-reactions, and pose a considerable safety risk. The direct nitration of 2,4-dinitrophenol ethers, obtained from the reaction of 2,4-dinitrochlorobenzene with alkoxides, provides a more practical route to picryl ethers on an industrial scale. ... 

Trinitrobenzene is present in crude TNT manufactured by mixed acid nitration and results from methyl group oxidation followed by decarboxylation." In fact, a convenient method for the synthesis of 1,3,5-trinitrobenzene involves oxidation of 2,4,6-trinitrotoluene with a solution of sodium dichromate in sulfuric acid, followed by decarboxylation of the resulting 2,4,6-trinitrobenzoic acid in boiling water." 1,3,5-Trinitrobenzene is prepared from 2,4,6-trinitro-m-xylene by a similar route." 2,4,6-Trinitroanisole can be prepared from the... 

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. 

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