4- Bromo-3-methylaniline

Nomenclature of Polysubstituted Benzenes Section 6.3D (a) 2,4-dichlorotoluene (b) 3-bromo-5-methylaniline ... 

Chloro-l-methyl-2-quinoxalinone (215), which cannot anionize, reacts readUy with iV -methylaniline. 6-Bromo-as-triazine-3,5-dione (216) is largely anionized by dimethylamine but not by thiourea... 

V-(Benzylaminoacetyl)-2-bromo-4-chloro-/V-methylaniline (1) gave l-benzyl-4-methyl-2,3(l//,4//)-quinoxalinedion (3), probably by aerial oxidation of the dihydro intermediate (2) [Bu3N, Ph3P, Pd(OAc)3, OP(NMe2)3, 110°C, CO or A (4 atm), 26 h 68% or 38%, respectively mechanism remains unclear].130... 

Fig. 1.11 Dissociation ranges of colour indicators for determination of the acidity function H0 in H2S04-H20 mixtures (1) p-nitroaniline, (2) o-nitroaniline, (3) p-chloro-o-nitroaniline, (4) p-nitrodiphenylamine, (5) 2,4-dichloro-6-nitroaniline, (6) p-nitroazobenzene, (7) 2,6-dinitro-4-methylaniline, (8) benzalacetophenone, (9) 6-bromo-2,4-dinitroaniline, (10) anthraquinone, (11) 2,4,6-trinitroaniline. (According to L. P. Hammett and A. J. Deyrup)...

Methoxyphenylurea, 31,10,13 Methyl -acetylbenzoate, 32, 81 Methyl acrylate, 30, 65 32, 86 y-Methylallophanate, 32, 62 Methylamine, 30, 60 4 -Methyl-2-aminobenzophenone, 32,12 N-Methylaniline, 30, 62 31,110 N-Methylarylamines, preparation by reductive alkylation, 30, 59, 60 Methylation, of e-caprolactam, 31, 72 of quinacetophenone, with dimethyl sulfate, 31, 91 with methyl iodide, 31, 90 2-Methyl-3,l,4-benzoxaz-4-one, 32, 12 N-Methyl-a-bromo-n-butyranilide, 30, 63... 

Methyl acetoacetate, 24, 70 4-Methvl-7-acetoxycoumarin, 21, 24 Methyl acrylate, 20, 64, 81 Methylal, 20, 60 Methylaminc, 20, 36 anhydrous, 20, 35 35% aqueous solution, 21, 81 generator, 20, 35 hydrochloride, 21, 82 N-Methylaminoaromatic acids, 22, 93 Methyl amyl ketone, 23, 70 Methylaniline, 20, 11, 66 Methylation, 20, 97 Methyl c[-bromo-/3-methoxypropio nate, 20, 81... 

Bromomethylaniline and derivs 2 B313—B314 dinitrobromomethylaniline 2 B313 2,6-dinitro-N-nitroso-4-bromo-N-methylaniline 2B313-B314... 

Dinitro-N -nitroso4-bromo-N-methylaniline 2B313-B314... 

Brom-4-nitroso-methylanilin in Ger], H3C.N C6H3(Br) N.OH or H3C.HN.CgH3(Br).NO. See 4-Nitroso-3-bromonethylaniline under Bromomethylaniline and Derivatives or 3-Bromo -l,4-benzoquinone-l-methylimine-4-oxime under Benzoquinone Oxime and Derivatives... 

Bromoaminotoluene or Bromotoluidine caM.eA Brom-methylanilin or Brom-aminotoluol in Get), C7HsNBr mw 186.06, N 7.53%. The Bromo-N methylaniline, isomers, Br.CgH4.NH.CH3, are described in Ref 1 and the Bromo-aminotoluene isomers, Br.CgH3NH2.CH3, are described in Ref 2. Most of these compds are liquids or low -melting crysts. Many form salts addn compds, some of which are unstable. Other props methods of prepn are given in the Refs Refs l)Beil 12, 637, (317) [341,345] 2)Beil 12, 837,838,839,873,991, (389,390 436) [455, 456,474,532]... 

Nitro-N-nitroso-4-bromo-N-methylaniline or ( 2-Hitro-4 bromophenyl) rnethylnitrosamine,... 

Refs l)Beil 12, [401,402] 2)W.G Macmillan T.H.Reade, JCS 1929, 2866 Dinitrobromomethylaniline, C7HgN304Br mw 276.06 N 15.22%. Three N-methyl derive, (02N)2CgH2Br.NH.CH3, are described in the lieerature 2,4-Dinit.ro-5-bromo-N-methylaniline, yel crysts(from ale), mp l49-l50° 2,4-Dinitro-6 -bromo-N-methylaniline, yel crysts(from AcOH), mp 147° and 2,6-Dinitro-4-bromo-N-metbylaniline, om ndls or yel crysts(from ale or petr eth), mp 104-6°(Ref 1). Two aminotoluene or methylaniline derivs, (OzN)2C6H(Br)NH2.CH3, are described in the literature 4,6-Dinitro-3-bromo-2-methyl-aniline, yel crysts, mp 200°-, and 3,5-Dinitro-2 -bromo-4-methylaniline, It yel ndls or prisms (from ale), mp 170-4°(Ref 2). Other props methods of prepn are given in the Refs Refs l)Beil 12, 761 [417, 418] 2)Beil 12, (397, 445) [540]... 

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 ... 

Dinitro-N-nitro-4-bromo-N-methylaniline or (2,6-Dinitro-4-bromophenyl)-methylnitramine, col crysts, mp 110° or It yel ndls(from ale), mp 113 4° was prepd by nitration of either 2-nitro 4 -bromo-N-methylaniline or (2,6-dinitro-4-bromo-phenyl)-methylnitrosamine(Refs 2,3 4). These compds will defgr or expl when heated above theit mp s, but theit expl props were not detd Refs l)Beil 12, 761 2)Beil 12, 762 [4191 3)J.J.Blanksma, Rec 21, 271-2(1902) 4)G.R. 

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... 

Phenyl ureas, carbamates, organochlorine insecticides, 4-bromophenol, captan, bromo- and chloroanilines, methylanilines, bromo- and chloro-nitrobenzenes, diphenyl amino folpet, hexachlorobenzene, naphthalene, phenol, simazine... 

To a solution of 4-bromo-2-methylaniline is added 13 g of chloroacetyl chloride. After the reaction is finished to the mixture id added a solution of 33 g sodium acetate in 138 ml of water. Chloroacetic acid 4-bromo-2-methylanilide is filtered yield 24 g, M.P. 135°C (crystallization from ethanol). 

Bromo-4-chlorobutanoyl bromide (300 mmol) was added to a solution of N-methylaniline (320 mmol) and triethylamine (330 mmol) in toluene (340 mL). The reaction was exothermic, and the mixture was cooled to maintain the temperature at about 40°C. After the addition was complete, the resulting mixture was stirred for 30 minutes, 150 mL water was added, and the mixture was stirred further. The aqueous and organic phases were separated, and the organic phase was washed with 5% hydrochloric acid and with water. The toluene was evaporated completely under vacuum to yield 86.3 g 2-bromo-4-chloro-N-methyl-N-phenylbutanamide (98% yield, approximately 95-96% pure). 

Alkoxy derivatives of biphenyl can be obtained either from alkoxy-anilines or by coupling with alkoxybenzenes. From diazotized p-bromo-aniline and anisole a 20% yield of 4-bromo-2 -methoxybiphenyl and a 7% yield of 4-bromo-4 -methoxybiphenyl are obtained. In connection with their studies on Cannabis Indica, Ghosh, Pascall, and Todd u prepared the highly substituted biphenyl compound, 2-cyano-5-methyl-2, 5 -dimethoxy-4 -n-amylbiphenyl (VII), in 27% yield from the nitrosoacetyl derivative of 2-cyano-5-methylaniline and 2,5-dimethoxy-n-amylben-zene. 

Another side reaction which occurs is reduction in the reaction the —N2C1 or —N(NO)COCH3 group is replaced by hydrogen. wi-Bromo-toluene was isolated in 6% yield from the reaction between the sodium diazotate from 2-bromo-4-methylaniline and benzene, and in 10% yield in a similar reaction from 2-methyl-4-bromoaniline.4 Some nitrobenzene is obtained in the preparation of 3-nitrobiphenyl from nitroso-w-nitro-acetanilide (p. 250). The source of the hydrogen effecting the reduction has not been determined. f... 

It has been demonstrated that the presence of chlorine or bromine in the nucleus facilitates replacement of the diazo group by hydrogen little or no ether formation occurs.26 Apparently iodine also favors the redudng action of alcohols, but this point has not been investigated carefully.26 27 No attempts to deaminate fluorinated amines are recorded. Representative of the effitiency with which ethanol reduces diazonium salts derived from halogenated amines are the deaminations of m-chloroaniline 26 (87% yield), of 2-bromo-4-methylaniline 28 (67% yield), of 2,4,6-tribfomoaniline 29 (ca. 80% yield), and of 2-carboxy-4-iodoaniline30 (ca. 45% yield) in the biphenyl series the deamination of VIII in 53% yield 31 may be dted. 

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