1 -methyl-2,4,6-trinitrobenzene

Synonyms CCRIS 1299 EINECS 204-289-6 Entsufon 1-Methyl-2,4,6-trinitrobenzene 2-Methyl-l,3,5-trinitrobenzene NCI-C56155 NSC 36949 TNT 2,4,6-TNT a-TNT TNT-tolite Tolit Tolite Trilit Trinitrotoluene sj/ 3-Trinitrotoluene Trinitrotoluol a-Trinitrotoluol sym-Tx -nitrotoluol Tritol Triton Trotyl Trotyl oil UN 0209 UN 1356. 

Synonyms/Trade Names 1-Methyl-2.4,6-trinitrobenzene TNT Trinitrotoluene sym-Trinitrotoluene Trinitrotoluol... 

Synonyms 2-methyl-1,3,5-trinitrobenzene 1 -methyl-2,4,6-trinitrobenzene 2,4,6-trinitrotoluol trotyl TNT... 

Other Names Toluene, 2,4,6-trinitro- a-TNT 1-Methyl-2,4,6-trinitrobenzene 2,4,6-Trinitrotoluene 2-Methyl-l,3,5-trinitrobenzene 4-Methyl-l,3,5-trinitrobenzene Gradetol NSC 36949 TNT ToUt Tolite Trinitrotoluene Tritol Tritol (explosive) Trotyl Trotyl oil sym-Trinitrotoluene sym-Trinitrotoluol... 

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... 

Such cyclohexadienes are easily oxidizable to benzenes (often by atmospheric oxygen), so this reaction becomes a method of alkylating and arylating suitably substituted (usually hindered) aryl ketones. A similar reaction has been reported for aromatic nitro compounds where 1,3,5-trinitrobenzene reacts with excess methyl-magnesium halide to give 2,4,6-trinitro-l,3,5-trimethylcyclohexane. Both... 

Methyl-1,3,5-trinitrobenzene, see 2,4,6-Trinitrotoluene Methyl tuads, see Thiram... 

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... 

CHEMICAL NAME = methyl-2,4,6-trinitrobenzene CAS NUMBER = 118-96-7 MOLECULAR FORMULA = (2HsN,0t MOLAR MASS = 227.1 g/mol... 

Dinitroanisole (3,5-DNAns), col crysts, mp 105-105.8°, bp - sublimes, d 1.558 at 20°/4°. Chemical reactions are described in Refs 12,13 29, Urbanski (Ref 14) studied eutectic mixts of 3,5-DNAns with hexanitro-mannitol and with nitroerythritol. Methods of prepn are discussed in Refs 2b,8,9,22,31 34. The method of prepn from 1,3,5-trinitrobenzene and Na methylate in anhyd methanol is described in detail in Ref 8... 

Trinitro-3 cbloroaniline or Methyl-(3 -chloro-2,4,6-trinitro-phenyl-ether), C1.C6H(N02)3.0.CH3 col crysts(from ale), mp 86-88° can be prepd by nitrating 3-chloronitro-anisole with nitric-sulfuric acid or by other methods. Its expl props were not detd Refs l)Beil 6, 292 [283] 2)J.J.Blanksma, Rec 21, 323(1902) [Called Oxymethylchloro-trinitrobenzene(1.3.2.4.6.)] 3)H.H.Schlubach F. Mergenthaler, Ber 58, 2734(1925 ) CA 20, 1395(1926)... 

An NMR method has been used to determine the association constant of benzo[6]thiophene with the electron acceptors 1,4-dinitrobenzene and 1,3,5-trinitrobenzene in chloroform solution.118 The 1H NMR spectra of some sulfur analogs of cholanthrene and methyl-cholanthrene have been analyzed.119... 

Trinitrobenzene gives red colors with ammonia and with aqueous alkalies. On standing in the cold with methyl alcoholic sodium methylate, it yields 3,5-dinitroanisol by a metathetical reaction.9... 

Highly-colored Jackson-Meisenheimer,or a, complexes of structure II or III are formed by addition to the ring system. The controversial history of the study of these compds has been well reviewed (Refs 44,46,51,70 82). They are formed in aq and anhydrous medium, and with a variety of organic and inorganic nucleophiles. Most of these studies have been made with 1,3,5 -trinitrobenzene rather than TNT, since the absence of a reactive methyl group in the former simplifies product isolation and identification. 

Sulfite ion forms a complex of structure III (Refs 44 80), which is a source of yield loss during the purification of TNT if the pH exceeds 8. Cyanide ion also forms a compd of structure III (Ref 44) the kinetics of this reaction has been studied (Ref 76), TNT, as the anion I, can react with itself to form adducts of type II it can similarly react with 13 >5-trinitrobenzene (Ref 57). Primary and secondary aliphatic amines form a-complexes (Refs 46 58), but tertiary amines (in an aprotic solvent), and aromatic amines, form ir-complexes instead. Upon soln in liq ammonia, a complex of type III is initially formed, with no evidence of I (Ref 105). With time, a second NH2 group becomes attached to the ring carbon with the methyl group this compd has cis- and transisomers. Removal of the ammonia gave a red... 

Rate and equilibrium constants have been reported for the reactions of butylamine, pyrrolidine, and piperidine with trinitrobenzene, ethyl 2,4,6-trinitrophenyl ether, and phenyl 2,4,6-trinitrophenyl ether in acetonitrile, hi these reactions, leading to cr-adduct formation and/or nucleophilic substitution, proton transfer may be rate limiting. Comparisons with data obtained in DMSO show that, while equilibrium constants for adduct formation are lower in acetonitrile, rate constants for proton transfer are higher. This probably reflects the stronger hydrogen bonding between DMSO and NH+ protons in ammonium ions and in zwitterions.113 Reaction of 1,3,5-trinitrobenzene with indole-3-carboxylate ions in methanol has been shown to yield the re-complex (26), which is the likely precursor of nitrogen- and carbon-bonded cr-adducts expected from the reaction.114 There is evidence for the intermediacy of adducts similar to (27) from the reaction of methyl 3,5-dinitrobenzoate with l,8-diazabicyclo[5.4.0]undec-8-ene (DBU) cyclization eventually yields 2-aminoindole derivatives.115... 

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