P-Chloro-N-methylaniline

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. 

The reaction of p-nitro-N,N-dimethylaniline with ozone was studied. Only side-chain oxidation products, p-rafro-N-methylaniline, p-nitro-N-methylformanilide, and a dimeric peroxide, di- [(N-methyl-N-p-nitrophenyl)aminomethyl peroxide, were formed. No N-oxide could be obtained. For comparison 2-carboxy-4-nitro-N,N-dimethylaniline, p-chloro-N,N-dimethylaniline, and N,N-dimethylaniline were ozonized. A mechanism is proposed. 

Materials. 2-Carboxy-4-nitro-N,N-dimethylaniline (I) was synthesized from its chloro analog with dimethylamine (aqueous solution), mp 164°-166°C. p-Chloro-N,N-dimethylaniline (IVb) and N,N-di-methylaniline (IVa) were commercially available in the pure state and were used as supplied. p-Nitro-N,N-dimethylaniline (IVc) was prepared from p-nitrochlorobenzene and dimethylamine (9) mp 166°C. 

Dimercaptotoluene(DMT) 3,4-dithiotoluene Hexachlorobenzene 50 ng/ml (ng/microliter) in dichloromethane Test mixture solution containing 12.5 40 p.g ml-1 (microgram per milliliter) each in dichloromethane of Trimethylphosphate 2,6-Dimethylphenol 5-Chloro-2-methylaniline Tri-n-butylphosphate 1ml 5-g 2ml 2ml... 

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