Trinitroanisole

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... 

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... 

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. 

Trinitrophenetole (8) can be prepared by heating 2,4,6-trinitroanisole (7) in ethanol containing a catalytic amount of sodium ethoxide. This reaction is so facile that methanol... 

Tire present paper describes a simple and convenient procedure for the identification of explosives viz Picramide Hexyl 2,4-Dinitrophenetole (DNP) Tetryl s-TNT s-TNB 2,4,6-Trinitroanisole (TNA) 2,4-Dinitroanisole (DNA) 2,4,6-Trinitro-phenetole (TNP) DNCB m-DNB and Picryl Chloride (PC) in ordnance stores as charge-transfer complexes with amines utilizing TLC... 

Introduction of Obermiiller Stability Test which consists of heating 1 to 2g NC in a small tube under vacuum at 135—140° and measuring the pressure of evolved gas by vacuum manometer (Ref 38a, pp 87—88) 1904—1905. 2,4,6-Trinitroanisole or Methyl Picrate was patented for use in smokeless proplnts in mixt with an equal amt of Pyrocellulose (Vol... 

Problem 11.62 Explain these observations (a) p-Nitrobenzenesulfonic acid is formed from the reaction of p-nitrochlorobenzene with NaHSO, but benzenesulfonic acid cannot be formed from chlorobenzene by this reaction. (f>) 2,4,6-Trinitroanisole with NaOC H, gives the same product as 2,4,6-trinitrophenetole with NaOCHj. <... 

This product was prepared by Blanksma [69] by the nitration of 2,4,6-trinitro-1,3,5-trimethylaminobenzene. The latter was obtained from 3,5-dichloro-(or di-bromo)-2,4,6,-trinitroanisole by the action of an alcoholic solution of methylamine. 

The reactivity data and the equilibrium constant for the formation of 9 are similar to those observed for the formation of the kinetically controlled adduct 6 (Table IV), which can be explained by the structural analogies of these adducts. In both cases the equilibrium constants are higher than the value reported for the formation of adduct 7 from 2,4,6-trinitroanisole (Table V). 

Kinetic and Equilibrium Data for Adduct Formation by the Reaction of 2,4,6-Trinitroanisole and MeO" in MeOH at 25°C6... 

---