4- Chloroaniline nitration

Alkylphenols, ammonia, asbestos, chlorinated paraffins, 4-chloroaniline, cyanide, detergents, di- -butyl phthalate, polyaromatic hydrocarbons (PAHs e.g. anthracene, benzopyrene, methylcholanthrene, /i-naphthoflavone), nitrate, nitrite, petroleum oil, phenol, pentachlorophenol, 4-nitrophenol, dinitro-o-cresol, polychlorinated biphenyls (PCBs especially coplanar), polychlorinated dioxins, polybrominated naphthalenes, /i-sitosterol, sulfide, thiourea, urea, acid water, coal dust... 

Chlorophenyl isothiocyanate has also been prepared by treating an alcoholic solution of sym-di-/)-chlorophenyl thiourea with iodine/ from ammonium -chloroplienyldithiocarbamate and lead nitrate/ (p. 72), and from the action of thiophosgene with /)-chloroaniline. ... 

The procedure given here is essentially that described previously by the submitters. -Chlorophenyl isothiocyanate has been prepared from sym-di-p-chloiophenyl thiourea with iodine in alcoholic solution, from ammonium p-chlorophenyldithio-carbamate and lead nitrate [cf. also Org. Syntheses, Coll. Vol. 1 447 (1932)], by the action of thiophosgene on />-chloroaniline and from -chloroaniline with thiocarbonyl tetrachloride in the presence of stannous chloride. ... 

A,A -Bis(3-aminopicryl)-l,2-ethanediamine (108) (m.p. 275 °C) is prepared from the reaction of ethylenediamine with two equivalents of 3-chloro-2,4,6-trinitroaniline. " The same chemists reported 3,3 -diamino-2,2 4,4, 6,6 -hexanitrodiphenylamine (109), a heat resistant explosive (m.p. 232-237 °C) prepared from the reaction of l,3-dichloro-4,6-dinitrobenzene with 3-chloroaniline followed by mixed acid nitration and subsequent chloro group displacement with ammonia. The potassium salt of 3,3 -diamino-2,2, 4,4, 6,6 -hexanitrodiphenylamine shows very high thermal stability. " ... 

The thermally insensitive explosive (112) is synthesized by a similar route from the reaction of l,3-dichloro-2,4,6-trinitrobenzene (106) (styphnyl chloride) with two equivalents of 3-chloroaniline, followed by nitration and subsequent displacement of the chloro groups with... 

T rinitro-3-chloroaniline or Methyl-(3 -chloro-2,4,6-trinitro-phenyl-ether), C1.CsH(N02)3.0.CH3 col crysts(from ale), mp 86-88° can be prepd by nitrating 3-chloronitro-anisole with nitric-sulfuric acid or by other methods. Its expl props were not detd... 

Chlorination of p-nitrochlorobenzene followed by reduction yields 3,4-dichloroaniline, though the process suffers from the presence of p-chloroaniline and 2,5-dichloroaniline (from o-nitrochlorobenzene in the starting material). A purer product is formed by nitration of o-dichlorobenzene followed by reduction. 

Carboxy-3,5-dichlorophenyl diazo-nium chloride, 31, 97 Catalyst, ammonium acetate, 31, 25, 27 copper chromite, 31, 32 ferric nitrate, hydrated, 31, 53 piperidine, 31, 35 piperidine acetate, 31, 57 Chlorination of anthranilic acid, 31, 96 Chlorine, 30, 24 31, 96 Chloroacetamide, 30, 22 Chloroacetonitrile, 30, 22 o-Chloroaniline, 31, 21... 

Coupling of diazotized p-chloroaniline with 4-methyl- and with 4,6-dimethyl-pyrimidine occurs at the 4-methyl group, and not, as previously reported, at the 5-position. Pyrimidines bearing unsaturated carbon side-chains are uncommon species. Timely, therefore, are reports on the synthesis of the hitherto undescribed 2-isopropenyl-pyrimidines by dehydrobromination of 2-(2 -bromoprop-2 -yl)-pyrimidines and of 2-alkynyl-pyrimidines by coupling of 2-iodo-pyrimidines with monosubstituted alkynes in the presence of bis(tri-phenylphosphine)palladium(ii) chIoride[Pd(PPh3)Cl2] cuprous iodide, and tri-ethylamine. Nitration of some pyrimidine bases and nucleotides has been... 

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