2.4- Dinitro-N-

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/... 

It is decompd by heat (Ref 9), or rapidly in boiling EtOH to give 2,4-dinitro-N-methylaniline (Ref 12)... 

Nitrations of aromatic amines often involve the intermediate formation of N-nitramines, although these are rarely seen under the strongly acidic conditions of mixed acid nitration (Section 4.5). N,2,4,6-Tetranitro-N-methylaniline (tetryl) is an important secondary high explosive usually synthesized from the nitration of N,N-dimethylaniline or 2,4-dinitro-N-methylaniline. ° The synthesis of tetryl is discussed in Section 5.14. 

Bei der Reaktion von Diisopropylamin mit l-Chlor-2,4-dinitro-benzol in Benzol bei 60° entsteht das erwartete N,N-Diisopropyl-2,4-dinitro-anilin nur in sehr geringer Ausbeute als Hauptprodukt entsteht das nur eine Isopropyl-Gruppe enthaltende 2,4-Dinitro-N-iso-propyl-anilin neben einer geringeren Menge an 2,4-Dinitro-N propyl-anilin1. Ahnliche Er-gebnisse erhalt man mit dem entsprechenden Aryl-fluorid und -bromid sowie bei Durch-fiihrung der Reaktion in Methanol oder Dimethyl-sulfoxid. 

CH -CN HN ch3 ci- no2 o2n HjC—OH RiickfluB, 3-4h (CH2I2-CN 3- (2,4-Dinitro-N-methyl-anilino) -propansdure-nitril 94 5... 

Dinitro-N, N-diethylaniline, exists as a- modification or stable form, orn-colored crysts (from acet), mp95° and a /3-modification or labile form, It-yel lfts (from MeOH), mp - stable in dry state at RT but goes to a- form at 90°or above forms an addn compd with 2,4-Dinitro-N,N-diethyl-aniline, 43 304 + c1oH13N3°4> mp 57-59°, which, on crystn from chlf + petr, separates into its components (Ref 3)... 

Dinttro-N-nitroso-diphenylamine [called Bis-(2-nitrophenyl)-nitrosamin in Gef], 03N.C6H4.N.N0.C(iH.4.N02 not obtd in pure state dec in ale to 2,2l-Dinitro-DPhA obtd with the 2,4l-Dinitro-N-nitroso deriv by nitrating 2-nitro-N-nitroso-diphenylamine in glac acet ac with nitric acid below 10° (Ref 1) 2,4>-Dinitro N-nitroso-diphenylamine,... 

DinitrO N-nitrosoacetanilide, (02 N)2-C6H3. N(NO). CO. CHj, mw 254.16, N 22.05%, oil, prepd by treating 2,4-dinitroacetanilide with nitrosyl chloride in the presence of K acetate. Its expl props were not investigated... 

Dinitro-N-nitraniline or N,2f4-Trinitro-aniline, (OjN CjHj. NHNO, also called... 

Tetranitro-N-methyl-diphenylamine or l-(21,4 - Dini tro-N-me thy lan ilino)-(2,4-dinitrobenzene), (OaN)iCsH3.N(CH3). C8H3-(NOa)a yel leafletsffrom ale or AcOH), mp 210° was prepd by nitrating 2,4-dinitro-N-methyl-diphenylamine as described in Ref 2. Its expt props were not examined... 

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 ... 

The n-butyl analogue of tetryl102 has been prepared by two methods (a) by condensing 2,4-dinitrochlorobenzene with n-butylamine to form 2,4-dinitro-n-butylaniline,103 and by the nitration of this product and (b) by the nitration in one step of n-butylaniline. The pure substance crystallizes from alcohol in... 

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