N-Methyl diphenylamine

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-Methyldipicrylamine. See 2,4,6,2, 4, 6 -Hexanitro-N-methyl-diphenylamine A440-R 3-Methyl-3-hydroperoxy-I-butyne. See under Acetylene Hydroperoxides A66-L 3-Methyl-3-hydroperoxy-l-pentyne. See under Acetylene Hydroperoxide A66-L o-Methylisoxazolecarboxylic Acid. See under Acetylene-Nitric Acid Reaction Studies... 

Trinitro-N-methyl-diphenylamine or l-(2 -Nitro-N-methylanilino)-(2,6-dinitro-benzene), 0,N.C,H .N(CH,).C,H,(NO,), yel ndls, mp 221 3° Was obtained on prolonged heating of a mtxt of 2,6-dinitrochloro-benzene, N-methyl-o-nitraniline, K,S04, Cul and amyl alcohol... 

Vacuum distillation of the product gives two fractions (1) comprising 92 per cent of the material boiling above chlorobenzene, which contains more than 96 per cent methylaniline, and 3 per cent ( 1.5 per cent) phenolic impurity (2) comprising 8 per cent higher-boiling-point material, which is chiefly a compound of the diphenylamine type, possibly N-methyl-diphenylamine, CHj N (CsHs). The presence of so much tertiary amine... 

Draw the diazonium salt formed when 2-aminonaphthalene reacts with acetic acid/NaN02- When this diazonium salt reacts with N-methyl diphenylamine, what is the structure of the resulting product If the diazonium salt reacts with 1,3,5-trimethoxybenzene, what is the resulting product ... 

If the proplnt is double-base, it has been observed that even the most stable propints bleach methyl violet paper in much shorter periods than one year. Investigations conducted by P.F. Macy at Picatinny Arsenal (Ref 4) showed that diphenylamine-stabilized doublebase proplnts in service storage at about 30°, may be considered of satisfactory stability if they do not cause complete bleaching of 0.1 N methyl violet paper in one month or less. Such proplnts always show satisfactory stability when subjected to the 65.5° Surveillance Test. It was observed at the same time, that double-base proplnts which had deteriorated, but were not yet hazardous, took from 11 to 24 days to bleach methyl violet paper at 30°... 

Preparation of 2 -Anilino-6 -di-n-butylamino-3 -methylfluoran (77k). To a solution of 2-(4-di-n-butylamino-2-hydroxybenzoyl)benzoic acid (0.1 mol) in 98% sulfuric acid (150 g) was added 4-methoxy-2-methyl-diphenylamine (0.1 mol) in limited amounts, while the temperature was maintained to not rise above 30°C. The resulting mixture was stirred at room temperature for 20h, and poured into ice water (1000ml). The precipitate was filtered off, washed with water, and then refluxed with a mixture of toluene (400 ml) and 20% aqueous sodium hydroxide (150 g) for 1 h. The toluene layer was separated, washed with hot water, and concentrated to leave ca. 100 ml of toluene. After being cooled, the precipitate was filtered off, and dried to give 2 -anilino-6 -di-n-butylamino-3 -methylfluoran in 90% yield as a white powder, mp 180-182°C. 

Products derived from intermediate zwitter-ions have been obtained in the reactions of benzynes with tertiary amines 1>. Benzyne generated by the reaction of -butyl-lithium with fluorobenzene interacts with AT.Af-dimethylaniline to yield iV-methyl diphenylamine and AT-ethyl diphenylamine 132,133). Using the reaction of chlorobenzene with n-butyl-lithium to generate benzyne resulted in the formation of increased amounts of 2-A7,AT-dimethylaminobiphenyl 132,133)... 

Tetranitro-3 methylnitramino-di phenyl-amine, also called in Beil N-Nitro-N-methyl-N -[2-nitro-phenyl)-2,4.6 trinitropbenylendia-min-( 1.3), 0JN-CiH4.NH-C6H(N0a)J-N(N02).CHs. Yel crysts (from AcOH), mp 200°(dec). Was prepd by treating 2,4,6-tr ini tro-3-me th y Ini tramino-diphenylamine with HNO,(d 1.49) at RT. Its expl props were not examined... 

Trinitro-3-methyl-diphenylamine or N-(2, 4 -DinitrophenylJ-4-nitro-m-toluidine, (0aN)aC6H3.NH.C8H3(CH3).N02 red prisms mp l7l-2c(from AcOH). Was obtained after a mixt of l-chloro-2,4-dinitrobenzene, 6-nitro-m-col ui dine and anhydrous AcONa had been heated for an hr at 190°... 

Tetremitro-4-met.hyldipkenylamine or N-(2, 4 -Dinitropkenyl)-2,6 dinitro-p-toluidine- (OaN)jC6Hj.NH.C8Hj(NOj)a.CH3 bright yel ndls (from ale), mp 169. Can be prepd by heating 2,2, 4 -trinicro-4-methyl-diphenylamine on a steam bath with coned HNOs(dI.42) (Ref 2). Its expl props were not examined... 

Trinitroanilino)-toluene N-(2, 4, 6 -Trinitmphenyl)-p-toluidine 2, -4, 6 -Trinitro-4-methyl-diphenylamine or Picryl-p-toluidine. Called James et al... 

Trinitro-2-methyl-diphenylamine or N-(2 i 4 DinitTophenyl) 4 nitro-o-toluidine, (02N)aC,H3.NH.CjHj(CHj).N0, orange prisms, mp 159°. Was o otaine 1 after 2-methyl-2, 4 -dinitrodiphenylamine had been shaken with glacial AcOH contg nitric acid (dl.42) and the mixt left at RT overnight Refs l)Beil—not found 2)G,G.Coker et... 

Further studies of the photochemically induced conversion of JV-methyl-diphenylamine into N-methylcarbazole have been reported.28 Two successive intermediates have been detected, namely the amine triplet and iV-methyl-4a,4b-dihydrocarbazole. Oxygen appears to participate in the overall reaction in two ways, viz. by dehydrogenation of the dihydrocarbazole intermediate to carbazole and by quenching the amine triplet. Non-oxidative cyclization of 5-(iV-methyl-anilino)- and 5-(iV-acetylanilino)-l,3-dimethyluracil (26) similarly gives the trans-dihydropyrimido[5,4-6]indoles (27) in high yield.24 Orbital symmetry arguments... 

The differences in protolytic behavior in response to changing the composition of aqueous acid solutions can be enormous. For example, ethanol in 70 wt % aqueous sulfuric acid (Lee and Cameron, 1971) is of equal basicity to N-methyl-2,4-dinitro-4 -bromodiphenylamine (Arnett and Mach, 1964). However, if one uses their individual acidity scales to predict their Bronsted basicities in water, it is easy to show that ethanol is nearly a million times more basic than this substituted diphenylamine. ... 

N-substituted diphenylamines also yielded phenothiazines on treatment with SOCI2 (33GEP562268). In this way, A-acetyldiphenylamine was quantitatively converted into tetrachlorophenothiazine, while A-phenyldiphenylamine (triphenyla-mine) gave 3,7-dichloro-10-(4 -chlorophenyl)-phenothiazine in 91% yield. In the first case, the chlorine atoms in positions 1 and 9 promote the removal of the acyl group from position 10 in the second case, the bulky N-substituent prevents the replacements of hydrogen from positions 1 and 9 by chlorine. The behavior of A-methyl-diphenylamine is intermediate in this respect 3,7-dichloro-lO-methylphenothiazine was isolated in 7% yield, along with tetrachlorophenothiazine (68AHC325). 

There are other stabilisers of a similar nature, which are 4-nitrodiphenylamine, 2-nitrodiphenylamine, N-methyl-p-nitroaniline and diphenylamine. 

Diphenylamine and certain derivatives of urea, N,N -diethyl-N,N -diphenyl urea (cen-tralite I) and N -methyl-N,N -diphenyl urea (acardite II) are used as stabilizers in propellant. 

Phenyl-a-naphthylamine Poly [[6-[(1,1,3,3-tetramethylbutyl) amino]-s-triazine-2,4-diyl] [(2,2,6,6-tetramethyl-4-piperidyl) imino] hexamethylene [(2,2,6,6-tetramethyl-4-piperidyl) imino]] Stearoyl p-aminophenol Styrenated diphenylamine N,N, N",N" -Tetrakis (4,6-bis (butyl-(N-methyl-2,2,6,6-tetramethylpiperidin-4-yl) amino) triazin-2-yl)-4,7-diazadecane-1,10-diamine... 

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