Methyl Trinitroanisol

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... 

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. 

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... 

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... 

Methyl Picrate or 2,4,6-Trinitrophenylmethyl Ethey) [Trinitroanisole in Fr Trinitroanisol or Trisol in Ger Trinitroanisol in Rus Trinitroanisolo in Italy Trinitroanisol in Spain Type 91 Explosive in Japan]. Pal. ... 

Trinitroanisol may also be prepared by the interaction of methyl iodide and silver picrate, and by the nitration of anisic acid, during which the carboxyl group is lost, but the most convenient method appears to be that of Jackson70 and his collaborators by which a methoxy group is substituted for chlorine in a nucleus already nitrated. A methyl alcohol solution of picryl... 

Preparation of Trinitroanisol. Thirty-five grams of picryl chloride is dissolved in 400 cc. of methyl alcohol with warming under reflux, and the solution is allowed to cool to 30-35°. A solution of 23 grams of sodium hydroxide in 35 cc. of water is added slowly through the condenser, while the liquid is cooled, if need be, to prevent it from boiling. The mixture is allowed to stand for an hour or two. The red precipitate is filtered off, washed with alcohol, and stirred up with water while strong hydrochloric acid is added until all red color has disappeared. The slightly yellowish, almost white, precipitate, washed with water for the removal of sodium chloride, dried, and recrystallized from methyl alcohol, yields pale yellow leaflets of trinitroanisol, m.p. 67-68°. From anhydrous solvents the substance separates in crystals which are practically white. 

Gazzolo (1900) thought that the intense colours produced from alkyl picrates and alkoxides could be best described by the quinonoid structure 1 (R = R = alkyl). The first strong chemical evidence that this was indeed the case was provided by Meisenheimer (1902). He obtained identical compounds by the addition of potassium methoxide to 2,4,6-trinitrophenetole and potassium ethoxide to 2,4,6-trinitroanisole. Acidification produced in each case a mixture of methyl and ethyl picrates. This led Meisenheimer to the conclusion that these compounds... 

Maxim [1] and du Pont de Nemours Inc. [2] were the first to suggest the application of the methyl ether, trinitroanisole, as an explosive. 

It is, therefore, necessary to use methyl alcohol as the solvent for the reciystallization of trinitroanisole. 

Purification of trinitroanisole. In the past trinitroanisole was purified by dissolving in methyl alcohol. The solution was filtered and the product precipitated by introducing the solution into water. Later the purification process was simplified, the crude trinitroanisole being agitated with hot water, the water decanted... 

By crystallization from methyl alcohol trinitrophenetole is converted into trinitroanisole. It also adds on a molecule of sodium or potassium alcoholate to form a bright coloured salt. 

TRINITROANISOLE (METHYL PICRATE) (TRINITROPHENYL METHYL ETHER)... 

Equilibrium constants and rates of fonnation for the adduct MI-733 have been measured and compared with those of 2,4,6-trinitroanisole. An annular nitrogen in the 4-position to a reactive center results in a relative decrease in stability of the Meisenheimer compound and an increase in its rate of formation when compared to the effect of a p-nitro The 4-methoxypyridone (W-736) has been used to prepare a number of 4-hydrazino- and substituted-4-amino-l-methyl-2-pyridones. ... 

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