Trinitro-N-methylaniline

Trinitro-N-methylanilines, C7H6N406, mw 242 15, N 23.14%, OB to C02 -72.7%. The following isomers have been reported in the literature ... 

N,2r4-Trinitro-N.-methylaniline (2,4-dinitrophenyl-methylnitramineJ, light yellow hexagonal crysts... 

Registry No 19092-03-6. It has been shown to be an intermediate in the prepn of Tetryl from N,N-dimethylaniline as it can be prepd from N,N-dimethylariiline or 2,4-dinitro-N-methylaniline by the action of 70% nitric acid in 90% yield (Refs 13 14) and can be nitrated to Tetryl with a mixt of 64% sulfuric acid, 15% nitric. acid, and-21%-w yield 91.9% (Ref 14). It can be isolated from commercial Tetryl and identified by thin layer chromatography (Ref 21) N,2,6-Trinitro-N-methylaniline (2,6-dinitrophenyl-methylnitramine), mp 110.8 874.9kcal/... 

Trinitro-N-methylaniline (N-methyl picra-mide), yellow needles from EtOH contg acid, mp /l4.8° (Refs 4 7) the UV spectrum has a peak at 340 and a shoulder at 410—20m (Ref 19) CA Registry No 1022-07-7. It is prepd by the hydrolysis of the N nitroso compd (see below) at 70—80° (Ref 5) by the action of coned sulfuric acid (Ref 8) or UV light (Ref 12) on Tetryl by the action of methyl amine on Ethyl Picrate (Ref 18) or Tetryl (Ref 7) or by the action of nitric acid (d 1.42g/cc) at 0° on N,N-dimethylaniline (Ref 10). It is present in crude Tetryl and is the active der-matitic agent in the latter (Ref 12). It can be isolated from crude Tetryl and identified by thin layer chromatography (Ref 21)... 

Dinitrophenylmethylnitramine, for example, on treatment with nitric and sulphuric acid, is rearranged to form trinitro-N-methylaniline ... 

Trinitro-N-methylaniline, mp 190° prepd by the oxidn of 2,3,4-trinitro-N,N-dimethyl- aniline (Encycl, Vol 5, D1315) with Cr trioxide (Ref 2)... 

N,2,4,5-Tetranitro-N-methylamline (2,4,5-trinitrophenyl-N-methylnitramine), needles from nitric acid-, mp 143.5° prepd by nitration of 2,4,5-trinitro-N-methylaniline, or by the action of 90% nitric acid on 2,4,5-trinitro-N,N-dimethylaniline (Refs 1 3) 2,3,4,6-Tetranitro-N-methylanilme, mp 127° prepd by the action of sulfuric acid on N,2,4,5-tetranitro-N-methylaniline (Refs 2 3)... 

Holingsworth, JCS 1959, 2423 N-Nitroso-2,4,6-trinitro-N-methylaniline (N-methyl-N-(2,4,6-trinitr6phenyl)nitrosamine, N-methyl-N-nitrosopicramide), C7HSNSO7, mw 271.15, N 25.83%, OB to CO2 -56.1%. Its expl props have not been investigated. Bright yellow leaflets or needles from EtOH, mp 106.5° (Ref 1) prepd by the action of nitrous acid on N-methylpicramide suspended in acet ac (Ref 2), or by allowing Tetryl to stand for 24 hours in the presence of coned sulfuric... 

Materials. 2, 3-dinitroaniline (8), -methyl-N, N-dimethyl-aniline (9), p-chloro-N, N-dimethylaniline (9), p-nitro-N, N-dimethylaniline (1 ), N-methyl-p-toluidine (11), p-chloro-N-methylaniline (11), N, 2, 4-trinitroaniline (12), 2, 4-dinitro-N-methylaniline (13), 2, 4-dinitro-N, N-dimethylaniline (13) and N, 2, 4-trinitro-N-methylaniline (14) were prepared by known methods. Spectroscopic grade nitromethane and methylene chloride were dried using a molecular sieve. The other substrates were either available from related studies or were purchased and purified by standard methods. 

N, 2,3,4-Tetranitro-N-methylaniline (2,3,4-trinitrophenyl-N-methylnitramine), mp 122.5° prepd by the nitration of 2,3,5-trinitro-N-niethyl-aniline with nitric acid (concn unspecified)... 

Investigated explosives included 2,4,6-trinitrotoluene (TNT), 2,4,6,N-tetranitro-N-methylaniline (tetryl), l,3,5-trinitro-l,3,5-triazacyclohexane (RDX), 1,3,5,7-tetranitro-l,3,5,7-tetrazacyclooctane (HMX) and pentaerythritol tetranitrate (PETN). The temperature of the injector, cooled with liquid CO2, was —5°C for 0.3 min, programmed from —5 to 250° C, at a rate of 200°C/min, with a final hold time of 8.4 min. The column temperature was 80° C for 2 min, programmed to 250° C at 25°C/min, with a final hold of 2 min. Electron ionization (El) in the positive-ion mode was used. Figure 4 shows the mass chromatograms of a mixture of explosives (lOppb each), extracted from water by Hquid—liquid extraction and X 100 concentration. Identification was based on typical fragment ions for each one of the explosives. 

The key representative of aromatic nitramines is the trinitro derivative of phenyl-methylnitramine—tetryl. This is 2,4,6-trinitrophenyhnethylnitramineorpicrylmethyl-nitramine or N-2,4,6-tetranitro-N-methylaniline. 

N 17.45%. The following isomers are described in the literature N,2,4-Trinitro-6 -bromo-N-metbylaniline 2,4-Dinitro-N-nitro-6 -bromo-N-methylaniline or (2,4-Dinitro-6 bromophenyl)-metbylnitramine, (OzN)2C6H2Br.-N(N02).CH3, col crysts, mp 125° was prepd by nitration of either 4-nitro-2-bromo-N-methylaniline ot 2,4-dinitro-6-bromo-N-methylaniline(Refs 1 3) and N, 2,6-Trinitro-4-bromo-N-methylaniline ... 

Trinitro-N-nitro-3-bromo-N-methylaniline or (2,4,6-T rinitro-3-bromophenyl)-metbylnitTamine, col crysts(from chlf), mp 127° was prepd by nitration of 2-nitro-5 bromo-N-methylaniline(Refs 1 3). These compds are expl, but their expl props were not detd... 

N,2,6 Trinitro 4 chloro-N-methylaniline or (2,6mDimtro-4-chlorophenyl)-methylnitramine, (02N)2C1.C6H2.N(N02)CH3, crysts, mp 100° was obtd by nitration of 2-nitro-4-chloro-N -methylaniline(Refs 1 2) and... 

OtherNames Aniline,A -methyl-M2,4,6-tetranitro- 2,4,6,A-Tetranitro-A-methylaniline 2,4,6-Tetryl 2,4,6-Trinitro-N-methyl-A-nitroaniline 2,4,6-Trinitrophenyl-A-methylnitramine 2,4,6-Trinitro-phenylmethylnitroamine CE A-Methyl-A,2,4,6-tetranitroaniline A-Methyl-A-picrylnitramine A-Picryl-A-methylnitramine NSC 2166 Nitramine Nitramine (indicator) Picrylmethylnitra-mine Picrylnitromethylamine Tetralit Tetralite Tetril Tetryl CA Index Name Benzenamine, A-methyl-A,2,4,6-tetranitro-CAS Registry Number 479-45-8 Merck Index Number 6573 Chemical Structure... 

N,N-Dimetby 1-2,4,6-trinitro-m-pbenylene-diamine, H3N.C6H(N02)a.N(CH3)2 crysts, mp 187° was prepd hy action of cold aq dimethylamine soln on 2,3,4,6-cetranitro-aniline, or by treating 2,3,4, 6 tetranitrodi-methylaniline with cold aq ammonia (Refs... 

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