Nitroaniline sulfate

In a 500-cc. round-bottom flask are placed 200 cc. of water, 100 cc. of concentrated sulfuric acid, and 50 g. of powdered w-nitroaniline. The hot mixture is shaken until solution is complete, and the hot m-nitroaniline sulfate solution is then poured into a 5-I. flask containing 1000 cc. of water and 800-1000 g. of cracked ice. During this procedure there must be good agitation, so that the m-nitroaniline sulfate forms a finely divided precipitate. Generally, the amount of ice used is sufficient to lower the temperature of the mixture to o°, but if not, more ice is added till o° is reached. 

A solution of 26 g. of sodium nitrite in 200 cc. of water is then rapidly added (Note 1) to the cold ra-nitroaniline sulfate suspension continual shaking or mechanical stirring should be used until the m-nitroaniline sulfate dissolves completely. This requires about five minutes, during which period the solution gradually darkens. A small flocculent precipitate forms at the same time and should be filtered off. 

In diazotizing w-nitroaniline sulfate, it is necessary to add the sodium nitrite as rapidly as possible in order to prevent any of the diazonium salt from coupling with undia/.otized m-nitroaniline and forming a yellow precipitate of diazoamino compound. The presence of the excess of sulfuric acid, which does not interfere with the formation of the t-nitrophenol, tends to avoid this same difficulty. 

It is prepd by the action of methylamine on 4-chloro-l-nitrobenzene (Ref 5) by the action of methyl iodide (Ref 6), or methyl sulfate on 4-nit roaniline (Ref 7) or by the hydrolysis of 4-nitro-N-methylformanilide with hot coned aq HC1 (Ref 8). In a study of the effect of nitric acid concn on the prods of the nitration of N,N-dimethylaniline to form Tetryl, it was isolated in low yield by the action of nitric acid, d 1.046g/cc, plus Na nitrite on N,N-dimethylaniline (Ref 10). A eutectic mixt with N-ethyl-4-nitroaniline has been patented as a stabilizer for NC (Ref 12). Studies at NPF indicate that 4-nitro-N-methyl-aniline is superior to Centralite, 2-nitrodiphenyl-amine, or Acardite in stabilizing. NC Refs 1) Beil 12, 586, (295) 1125 ... 

Nitroaniline reacts almost explosively [1], and 4-nitroaniline, 4-nitroacetanilide, aminonitrobiphenyls, aminonitronaphthalenes and their various derivatives [2], as well as some nitro-N-heterocycles [1,2], also react vigorously. 4-Nitroanilinium sulfate and 4-nitroaniline-2-sulfonic acid and its salts also generate foams when heated without sulfuric acid. The mechanism is not clear, but involves generation of a polymeric matrix foamed by sulfur dioxide and water eliminated during the reaction [1]... 

The metabolism of an oral dose of 50-100 mg/kg "C-1,3-DNB was followed in rabbits (Parke 1961). Of the metabolites detected in urine, 30% were conjugated with glucuronic acid and 6% with sulfate. The major urinary metabolites of 1,3-DNB were 2,4-diaminophenol (31%), 1,3-phenylenediamine (25%), 1,3-nitroaniline (18%), and 2-amino-4-nitrophenol (14%). Other minor metabolites comprising about 20% of the label were oxidation and reduction products and azoxy dimers. 

Chloro-2,5-diethoxynitrobenzene, 3301 6-Chloro-2,4-dinitrobenzenediazoniimi hydrogen sulfate, 2102 A-Chloro-4-nitroaniline, 2231... 

Synonym Neatsfoot Oil Necatorina Nechexane Neutral Ahhonium Pluoride Neutral Anhydrous Calcium Hypochlorite Neutral Lead Acetate Neutral Nicotine Sulfate Neutral Potassium Chromate Neutral Sodium Chromatetanhydrous Neutral Verdigris Nickel Acetate Nickel Acetate Tetrahyorate Nickel Ammonium Sulfate Nickel Ammonium Sulfate Hexahydrate Nickel Bromide Nickel Bromide Trihydrate Nickel Carbonyl Nickel Chloride Nickel Chloride Nickel Cyanide Nickel Iiu Fluoborate Nickel Fluoroborate Solution Nickel Fluoroborate Nickel Formate Nickel Formate Dihyorate Nickel Nitrate Nickel Nitrate Hexahydrate Nickel Sulfate Nickel Tetracarbokyl Nickelous Acetate Nickelous Sulfate Nicotine Nicotine Sulfate Nifos Nitralin Nitram O-Nitraniline P-Nitraniline Nitric Acid Nitric Acid, Aluminum Salt Nitric Acid, Iron (111) Salt Compound Name Oil Neatsfoot Carbon Tetrachloride Neohexane Ammonium Fluoride Calcium Hypochlorite Lead Acetate Nicotine Sulfate Potassium Chromate Sodium Chromate Copper Acetate Nickel Acetate Nickel Acetate Nickel Ammonium Sulfate Nickel Ammonium Sulfate Nickel Bromide Nickel Bromide Nickel Carbonyl Nickel Chloride Nickel Chloride Nickel Cyanide Nickel Fluoroborate Nickel Fluoroborate Nickel Fluoroborate Nickel Formate Nickel Formate Nickel Nitrate Nickel Nitrate Nickel Sulfate Nickel Carbonyl Nickel Acetate Nickel Sulfate Nicotine Nicotine Sulfate Tetraethyl Pyrophosphate Nitralin Ammonium Nitrate 2-Nitroaniline 4-Nitroaniline Nitric Acid Aluminum Nitrate Ferric Nitrate... 

There is a preparative hazard for this reaction product of iV-methyl-p-nitroaniline and carbyl sulfate . 

N-Methyl-p-nitroaniline Nickel Raney Palladium on carbon Calcium sulfate... 

The above procedure is a modification of the method of Groll 1 a more laborious method of purification has been described. w-Nitrodimethylaniline can also be prepared by methylation of w-nitroaniline using methyl sulfate.3... 

A solution of 20 g. (0.165 mole) of m-xylidine in 200 g. of concentrated sulfuric acid is cooled to 5°, and 16.5 g. of concentrated nitric acid is added slowly with stirring. During this operation and for an additional 30-minute stirring period, the temperature of the reaction mixture is held below 15°. Pouring the mixture on crushed ice precipitates the amine sulfate, which is separated by filtration. The solid is treated with 10% aqueous sodium carbonate solution, and the resulting free amine is recrystallized from a 50% aqueous ethanol solution. The yield of 2,4-dimethyl-5-nitroaniline is 23 g. (84%), and the product melts at 123-124°. 

Preparation of m-nitrophenol from m-nitroaniline 557 A cold mixture of water (450 ml and concentrated sulfuric acid (330 ml) is poured, with stirring, over finely powdered ra-nitro-aniline (210 g), and ice (800 g) is added. When the mixture has become homogeneous, a solution of sodium nitrite (105 g) in water (250 ml) is run in during 8-10 min from a dropping funnel until the starch-iodine reaction remains positive. The temperature is kept between 0° and 5° and the mixture is stirred for a further 5-10 min. Then the m-nitrobenzenediazonium sulfate is allowed to settle, the supernatant liquid is poured off and the solid washed, if necessary, with water by decantation in order to purify the salt filtration is necessary only when gross impurity is present. 

First, 100 parts of m-dinitrobenzene is added to 1,000 parts of water at 90 C contained in a reducer fitted with a reflux condenser and a propeller-type stirrer. Upon emulsification, 245 parts of sodium sulfide (9HaO), dissolved in a minimum of water, is gradually run in. The dinitro compound is gradually reduced to m-nitroaniline, the end point being determined by the formation of a definite black streak when ferrous sulfate solution is added to filter paper spotted with some of the reducer liquor. 

Oiaminophenol. 4-Hydroxy-w-phenylenediamine [95-86-3] (12) forms leaflets that darken on exposure to ait. It is soluble in acid, alkali, ethanol, and acetone and is sparingly soluble in chloroform, diethji ether, and ligroin. 2,4-IDiaminophenol usually is sold as the sulfate [74283-34 ] (Diamol) or dihydtochlotide salt [137-09-7] (Acrol, Amidol). 2,4-Diaminophenol can be prepared from 2,4-dinitrophenol by catalytic hydrogenation or, less conveniendy, by metal reduction in acid solution (Bfichamp method) (169,170). Alternatively, electrolytic reduction and subsequent hydroxjiation of 1,3-dinitrobenzene or 3-nitroaniLine in sulfuric acid can be undertaken (171,172). 

Fast red KB amine Fast red KB base Fast red KB salt. See 5-Chloro-o-toluidine Fast red SG Base. See 2-Methyl-5-nitroaniline Fast scarlet. See Direct red 2 Fast scarlet R. See 2-Methoxy-5-nitroaniline Fast scarlet G. See 2-Methyl-5-nitroaniline Fast scarlet 2G. See 2,5-Dichloroaniline Fast white. See Lead sulfate Fast yellow. See 4-Dimethylaminobenzene Fast yellow A. See Direct yellow 11 Fast yellow AT. See o-Ami noazotoluene Fat black. See Solvent black 3 Fat, lard. See Lard Fat Orange II. See Solvent orange 2 Fat rown B. See Solvent red 3 Fats and glyceridic oils, vegetable, hydrogenated. See Hydrogenated vegetable oil... 

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