2-Amino-4,6-dinitrophenol

Amino-4-nitropheno1 is produced commercially by the partial reduction of 2,4-dinitrophenol This reduction may be achieved electrolyticaHy using vanadium (159) or chemically with polysulftde, sodium hydrosulftde, or hydrazine and copper (160). Alternatively, 2-acetamidophenol or 2-methylbenzoxazole may be nitrated in sulfuric acid to yield a mixture of 4- and 5-nitro derivatives that are then separated and hydrolyzed with sodium hydroxide (161). 

Amino-4,6-dinitrophenol. This derivative (10), also known as picramic acid, forms dark red needles from ethanol and prisms from... 

The sulfhydiyl group in cysteine can be selectively protected in the presence of the amino group by reaction with 2,4-dinitrophenol at pH 5-6. ... 

Recent examples of this synthesis are of two types. The first involves condensation of the activated phenol, 2-amino-4,6-dinitrophenol (346a) with 2-dimethyl-amino-3,3-dimethyl-3//-azirine (346b) (in MeCN, 0°C- 20°C, A, 24 h) to afford a separable mixture of four products, one of which was 2-dimethylamino-3,3-dimethyl-5,7-dinitro-3,4-dihydroquinoxaline (346c) ( 20% yield) and another its hydrolysis product, 3,3-dimethyl-5,7-dinitro-3,4-dihydro-2(l//)-quinoxalinone (346d) ( 8%) the mechanism of such condensations has been discussed. ... 

The 2,4-dinitrophenylhydrazone of patulin and other mono-2,4-dinitrophenylhydra-zones form red zones, 2-s c-butyl-4-amino-6-nitrophenol appears as a red-orange zone while dinitrophenols and their esters are colored yellow [14]. A whole range of organophosphorus pesticides do not give any reaction [12]. 

Shortly after Perkin had produced the first commercially successful dyestuff, a discovery was made which led to what is now the dominant chemical class of dyestuffs, the azo dyes. This development stemmed from the work of Peter Griess, who in 1858 passed nitrous fumes (which correspond to the formula N203) into a cold alcoholic solution of 2-aminO 4,6 dinitrophenol (picramic acid) and isolated a cationic product, the properties of which showed it to be a member of a new class of compounds [1]. Griess extended his investigations to other primary aromatic amines and showed his reaction to be generally applicable. He named the products diazo compounds and the reaction came to be known as the diazotisation reaction. This reaction can be represented most simply by Scheme 4.1, in which HX stands for a strong monobasic acid and Ar is any aromatic or heteroaromatic nucleus. 

Such reductions may result in loss or diminution of the harmful effects as microorganisms convert the broad-spectrum poison 2,4-dinitrophenol to 2-amino-4-and 4-amino-2-nitrophenol, the fungicide pentachloronitrobenzene to penta-chloroaniline, and the insecticide Parathion to aminoparathion. 

Titanium ions can also he used as redox catalysts for the indirect cathodic reduction of nitro compounds (417). The electroreduction is carried out in an H20-H2S04/Ti(S04)2-(Pb/Cu) system at 45 80°C under 5 20Am . Nitrobenzene, dinitrobenzene, nitrotoluene, 2,4-dinitrotoluene, 2-nitro-m-xylene, nitro-phenol, 2,4-dinitrophenol, nitrophenetole, o-nitroanisole, 4-nitrochlorotoluene, ni-trobenzenesulfonic acid, and 4,4 -dinitro-stilbene-2,2 -disulfonic acid can all be reduced by this procedure to the corresponding amino compounds (418) in good yields (Scheme 146) [513-516]. Tin... 

Acetamido-4-amino-6-chloro-s-triazine, see Atrazine Acetanilide, see Aniline, Chlorobenzene, Vinclozolin Acetic acid, see Acenaphthene, Acetaldehyde, Acetic anhydride. Acetone, Acetonitrile, Acrolein, Acrylonitrile, Aldicarb. Amyl acetate, sec-Amyl acetate, Bis(2-ethylhexyl) phthalate. Butyl acetate, sec-Butyl acetate, ferf-Butyl acetate, 2-Chlorophenol, Diazinon. 2,4-Dimethylphenol, 2,4-Dinitrophenol, 2,4-Dinitrotoluene, 1,4-Dioxane, 1,2-Diphenylhydrazine, Esfenvalerate. Ethyl acetate, Flucvthrinate. Formic acid, sec-Hexyl acetate. Isopropyl acetate, Isoamyl acetate. Isobutyl acetate, Methanol. Methyl acetate. 2-Methvl-2-butene. Methyl ferf-butvl ether. Methyl cellosolve acetate. 2-Methvlphenol. Methomvl. 4-Nitrophenol, Pentachlorophenol, Phenol. Propyl acetate. 1,1,1-Trichloroethane, Vinyl acetate. Vinyl chloride Acetoacetic acid, see Mevinphos Acetone, see Acrolein. Acrylonitrile. Atrazine. Butane. 

Diazo-4,6-dinitrophenol (DDNP or DINOL) (53) can be prepared from the diazotization of 2-amino-4,6-dinitrophenol (52) (picramic acid) with nitrous acid " the latter is obtained from the selective reduction of picric acid with ammonium sulfide." 2-Diazo-4,6-dinitrophenol (53) is widely used as an initiating charge in detonators and caps. 

The nitration of 2-amino-4,6-dinitrotoluene (63) with a mixtnre of nitric acid in sulfuric and acetic acids yields 2-diazo-3-methyl-4,6-dinitrophenol (65) in 75 % yield without isolation of the intermediate nitramine (64)." ... 

In the only study that measured 1,3-DNB metabolite production in humans after dermal exposure, the total production of both amino and nitro metabolites in urine was reported using 2,4-dinitrophenol as a standard (Ishihara et al. 1976). The results indicate that 1,3-DNB (in solution) rapidly penetrated skin and was also rapidly converted and excreted in urine. A maximum amount of amino and nitro metabolites was reached within the first hour after exposure and returned to normal levels after 10 hours. The limitations of this study are a small sample size (one person) and no detailed information on the nature of 1,3-DNB metabolites. 

Very little information is available about the nature of urinary metabolites of 1,3-DNB in humans. In a study that evaluated 1,3-DNB urinary metabolites after a single dermal exposure, amino and nitro metabolites were grouped together and reported as a single value relative to the level of 2,4-dinitrophenol as a standard (Ishihara et al. 1976). Amino and nitro metabolites may be derived from a variety of nitroaromatic compounds thus, they are not specific for 1,3-DNB. 

Direct amination of benzo[l,2-aqueous base with hydroxylamine-0-sulfonic acid gives a mixture of three diamino derivatives and two monoamino derivatives (Equation (15)). The combined yields of diamino and monoamino products are 45% and 48%, respectively. The three diamino derivatives can be separated by fractional crystallization from ethanol <86JOC979>. A-Amination of triazoles can also be achieved by treatment with NaH in DMF followed by O-amino-2,4-dinitrophenol <85TL335> or 0-(mesitylsulfonyl)hydroxyamine (9lJCS(Pl)2045>. 

Ammonium 2-amino-4,6-dinitrophenolate, Ammonium 2-amino-4,6-dinitropicrate... 

Dinitrophenylurea 2-Amino-4,6-dinitrophenol 2-Chloro- 1-phenylethanone 2-Chloroacetophenone 2-Chloroethenyl arsenous dichloride 2-Chloro-N,N-bis(2-chlorobutyl)butaneamine 2-Chloro-N,N-bis(2-chloroethyl)ethaneamine 2-Chlorovinyldichloroarsine... 

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