P-Dinitrophenol

Other Names P-Dinitrophenol 2,6-DNP 2,6-Dinitrophenol NSC 6215 Phenol, P-dinitro- o-Dinitrophenol 

CA Index Name Phenol, 2,6-dinitro-CAS Registry Number 573-56-8 Merck Index Number 3282 Chemical Structure 

Chemical/Dye Class Nitro Molecular Formula C6H4N2O5 Molecular Weight 184.11 pH Range 1.7-4.4 

Solubility Sparingly soluble in water soluble in ethanol, chloroform, ether Melting Point 63-64°C 

Boiling Point (Calcd.) 239.0 + 20.0°C Pressure 760 Ton-Synthesis Synthetic methodsi-  

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P-Dinitrophenol. Bright lemon yellow crystalline needles melting point 64.5° sintering at 62.5°. Indicator solution same as for the a-preparation. 

P-DINITROPHENOL (573-56-8) Combustible solid (flash point unknown). Contact with alkaline materials or UVlight may cause decomposition. Reacts with strong oxidizers, with a risk of fire or explosions. Incompatible with boranes, caustics, aliphatic amines, amides, isocyanates, nitric acid, sulfuric acid. 

In a 1 htre round bottomed flask equipped with a reflux condenser place a solution of 62 -5 g. of anhydroas sodium carbonate in 500 ml. of water and add 50 g. of commercial 2 4-dinitro-l-chlorobenzene. Reflux the mixture for 24 hours or until the oil passes into solution. Acidify the yellow solution with hj drochloric acid and, when cold, filter the crystaUine dinitrophenol which has separated. Dry the product upon filter paper in the air. The yield is 46 g. If the m.p, differs appreciably from 114°, recrystallisc from alcohol or from water. 

The procedure of simultaneous extracting-spectrophotometric determination of nitrophenols in wastewater is proposed on the example of the analysis of mixtures of mono-, di-, and trinitrophenols. The procedure consists of extraction concentrating in an acid medium, and sequential back-extractions under various pH. Such procedures give possibility for isolation o-, m-, p-nitrophenols, a-, P-, y-dinitrophenols and trinitrophenol in separate groups. Simultaneous determination is carried out by summary light-absorption of nitrophenol-ions. The error of determination concentrations on maximum contaminant level in natural waters doesn t exceed 10%. The peculiarities of application of the sequential extractions under fixed pH were studied on the example of mixture of simplest phenols (phenol, o-, m-, />-cresols). The procedure of their determination is based on the extraction to carbon tetrachloride, subsequent back-extraction and spectrophotometric measurement of interaction products with diazo-p-nitroaniline. 

Figure 13.15 Chromatograms obtained by on-line ti ace enrichment of 50 ml of Ebro river water with and without the addition of different volumes of 10% Na2S03 solution for every 100 ml of sample (a) blank with the addition of 1000 p.1 of sulfite (b) spiked with 4 p.g 1 of the analytes and 1000 p.1 of sulfite (c) spiked with 4 p.g 1 of the analytes and 500 p.1 of sulfite (d) spiked with 4 p.g 1 of the analytes without sulfite. Peak identification is as follows 1, oxamyl 2, methomyl 3, phenol 4, 4-niti ophenol 5, 2,4-dinitrophenol 6, 2-chlorophenol 7, bentazone 8, simazine 9, MCPA 10, atrazine. Reprinted from Journal of Chromatography, A 803, N. Masque et ai, New chemically modified polymeric resin for solid-phase extraction of pesticides and phenolic compounds from water , pp. 147-155, copyright 1998, with permission from Elsevier Science.

Phenol 2,4,6-trichlorophenol p-chloro-m-cresol 2-chlorophe-nol 2,4-dichlorophenol 2,4,-dimethylphenol 2-nitrophenol 4-nitrophenol 2,4-dinitrophenol and pentachlorophenol... 

The permanganate oxidation of phenols is complicated by the intervention of lower oxidation states of manganese, (c/. the oxidation of toluene, p. 298). For example, the oxidation of 2,6-dinitrophenol in weakly acidic solution displays an induction period, following second-order kinetics thereafter. However, addition of potassium fluoride inhibits reaction almost completely, but manganous ions strongly accelerate it. 

Ebert S, P-G Rieger, H-J Knackmuss (1999) Function of coenzyme P420 in aerobic catabolism of 2,4,6-trinitro-phenol and 2,4-dinitrophenol by Nocardiodes simplex FJ2-1 A. J Bacterial 181 2669-2674. 

OS 31] [R 16c] ]P 23] The levels of dinitrobenzene, dinitrophenol and picric acid in the organic phase during benzene nitration in a micro reactor were monitored [31]. Picric acid levels were no higher than 100 ppm for all experiments conducted. Dinitrobenzene was the largest impurity fraction. A study revealed contents < 1000 ppm up to 34 mass-% on increasing the sulfuric acid content from 70 to 85%. 

RCH(OH)=CHCOR or p-keto esters RCH(OH)=CHCOOR ) dissolve in dilute sodium hydroxide solution, i.e., contain an acidic group of sufficient strength to react with the alkah. Carboxylic acids and sulphonic acids are soluble in dilute solutions of sodium bicarbonate some negatively-substituted phenols, for example, picric acid, 2 4 6-tribromo-phenol and 2 4-dinitrophenol, are strongly acidic and also dissolve in dilute sodium bicarbonate solution. 

Gritzapis, P. and Timotheou-Potamia, M. (1989). Determination of reducing sugars with a 2,4-dinitrophenolate-selective membrane electrode. Anal. Chim. Acta 218, 37-46. 

At first we determined, by means of the DVP method, ifTMAX of 2,4-dinitro-phenolate, 2,5-dinitrophenol picrate, acetate and benzoate, which lay between 10 3 and 10 5. Next, separate potentiometric titrations of 2,5-dinitrophenol and picric acid were carried out on the basis of the previously known (see above) ptfax = 6.5 and P hx2- = 100 for 2,5-dinitrophenol and p.fiTHX = 3.0 for picric acid, we calculated titration curves for estimated values of 0 and obtained, for the best fit between the experimental and calculated curves, K o = 10 21 for both 2,5-dinitrophenol and picric acid. In both instances changing fTMA0H for 1 to 10 6 did not alter the calculated titration curve. Finally, for potentiometric titrations of other acids with TMAOH while using / TMAX values from DVP results, in addition to Kn 0 = 10 21, we obtained the best fit between the experimental and calculated curves again when pifbenzoic acid = 1 (see Fig. 4.12)... 

This salt of the mono-aci- p-quinonoid form of 2-hydroxymercurio-4,6-dinitrophenol explodes violently on strong heating. 

McKim, J.M., P.K. Schmieder, R.W. Carlson, and E.P. Hunt. 1987. Use of respiratory-cardiovascular responses of rainbow trout (Salmo gairdneri) in identifying acute toxicity syndromes in fish. 1. Pentachlorophenol, 2,4-dinitrophenol, tricaine methanesulfonate and 1-octanol. Environ. Toxicol. Chem. 6 295-312. 

By further nitration with more concentrated acid o- and p-nitro-phenols are converted into the same 2 4-dinitrophenol, and finally into picric acid. Polynitro-derivatives of benzene, such as picric acid and trinitrotoluene, can be caused to explode by detonation with mercury fulminate or lead azide. (The formulae of these two compounds should be written.) They are endothermic, i.e. the oxygen of the nitro-group can oxidise carbon and hydrogen within the molecule and heat is liberated. This intramolecular combustion is rather considerable in the case of picric acid, which is decomposed in accordance with the equation ... 

Since mtro-groups in the o- and p-positions increase the mobility of halogens directly attached to the aromatic ring (p. 106), nitrophenols can also be obtained from chloronitrobenzenes. Thus p-chloronitro-benzene can be decomposed by alkalis in the autoclave, and 2 4-dinitrophenol, an important intermediate product for the manufacture of sulphur dyes, is produced from the corresponding chlorobenzene by an even milder treatment. 

The electrochemical behavior of the components of a commercial plant growth stimulator (Sviton) was studied. This included determination of o-nitrophenol, p-nitrophenol, 2-methoxy-5-nitrophenol and 2,4-dinitrophenol by differential pulse voltammetry at a hanging mercury drop electrode. The optimum conditions were established for their quantitation over the 1 x 10 7 to 1 x 10-5 M range516. 

AI3-00040, see Cyclohexanol AI3-00041, see Cyclohexanone AI3-00045, see Diacetone alcohol AI3-00046, see Isophorone AI3-00050, see 1,4-Dichlorobenzene AI3-00052, see Trichloroethylene AI3-00053, see 1,2-Dichlorobenzene AI3-00054, see Acrylonitrile AI3-00072, see Hydroquinone AI3-00075, see p-Chloro-rrr-cresol AI3-00078, see 2,4-Dichlorophenol AI3-00085, see 1-Naphthylamine AI3-00100, see Nitroethane AI3-00105, see Anthracene AI3-00109, see 2-Nitropropane AI3-00111, see Nitromethane AI3-00118, see ferf-Butylbenzene AI3-00119, see Butylbenzene AI3-00121, see sec-Butylbenzene AI3-00124, see 4-Aminobiphenyl AI3-00128, see Acenaphthene AI3-00134, see Pentachlorophenol AI3-00137, see 2-Methylphenol AI3-00140, see Benzidine AI3-00142, see 2,4,6-Trichlorophenol AI3-00150, see 4-Methylphenol AI3-00154, see 4,6-Dinitro-o-cresol AI3-00262, see Dimethyl phthalate AI3-00278, see Naphthalene AI3-00283, see Di-rj-butyl phthalate AI3-00327, see Acetonitrile AI3-00329, see Diethyl phthalate AI3-00399, see Tributyl phosphate AI3-00404, see Ethyl acetate AI3-00405, see 1-Butanol AI3-00406, see Butyl acetate AI3-00407, see Ethyl formate AI3-00408, see Methyl formate AI3-00409, see Methanol AI3-00520, see Tri-ocresyl phosphate AI3-00576, see Isoamyl acetate AI3-00633, see Hexachloroethane AI3-00635, see 4-Nitrobiphenyl AI3-00698, see IV-Nitrosodiphenylamine AI3-00710, see p-Phenylenediamine AI3-00749, see Phenyl ether AI3-00790, see Phenanthrene AI3-00808, see Benzene AI3-00867, see Chrysene AI3-00987, see Thiram AI3-01021, see 4-Chlorophenyl phenyl ether AI3-01055, see 1.4-Dioxane AI3-01171, see Furfuryl alcohol AI3-01229, see 4-Methyl-2-pentanone AI3-01230, see 2-Heptanone AI3-01231, see Morpholine AI3-01236, see 2-Ethoxyethanol AI3-01238, see Acetone AI3-01239, see Nitrobenzene AI3-01240, see I idine AI3-01256, see Decahydronaphthalene AI3-01288, see ferf-Butyl alcohol AI3-01445, see Bis(2-chloroethoxy)methane AI3-01501, see 2,4-Toluene diisocyanate AI3-01506, see p,p -DDT AI3-01535, see 2,4-Dinitrophenol AI3-01537, see 2-Chloronaphthalene... 

CF 2, see 1,1,1-Trichloroethane CFC 11, see Trichlorofluoromethane CFC 21, see Dichlorofluoromethane CFC 112, see 1,2-Difluorotetrachloroethane CFC 112a, see 1,1-Difluorotetrachloroethane CFC 113, see 1,1,2-Trichlorotrifluoroethane Chelen, see Chloroethane Chemform, see Methoxychlor Chemathion, see Malathion Chemical 109, see ANTU Chemical mace, see a-Chloroacetophenone Chemox PE, see 2,4-Dinitrophenol Chempenta, see Pentachlorophenol Chemphene, see Toxaphene Chemrat, see Pindone Chemsect DNOC, see 4,6-Dinitro-ocresol Chemtol, see Pentachlorophenol Chevron acetone, see Acetone Chimec NR, see 2-Bntoxyethanol Chinone, see / Qninone Chinnfnr, see Carbofuran Chipco thiram 75, see Thiram Chipco turf herbicide "D", see 2,4-D Chladone 11, see Trichlorofluoromethane Chlon, see Pentachlorophenol Chlorallylene, see Allyl chloride Chloran, see Lindane 4-Chloraniline, see 4-Chloroaniline p-Chloraniline, see 4-Chloroaniline Chlorbenzene, see Chlorobenzene Chlorbenzol, see Chlorobenzene p-Chlor-ro-cresol, see p-Chloro-ro-cresol Chlordantoin, see Amyl acetate Chlordan, see Chlordane... 

Nitric acid, see 1-Butene, o-Chloronitrobenzene. p-Chloronitrobenzene, Chloropicrin, 2,3-Dichloronitrobenzene. 3.4-Dichloronitrobenzene. 2,4-Dinitrophenol, Formaldehyde, Isopropylbenzene, Methanol, Methyl mercaptan, 2-Methylphenol, 2-Methylpropene, Methyl sulfide. Nitrobenzene, 2-Nitrophenol, 4-Nitrophenol,... 

Moreover, uncoupHng experiments using Escherichia coli cells were described. An addition of glucose to stationary E. coli cells leads to an increase of fluorescence intensity in the region of NAD(P)H, because it is formed in the glycolysis. This increase was stopped abruptly by addition of 2,4 dinitrophenol (DNP), which effects a decrease in the fluorescence signal according to the theory of uncoupled oxidative phosphorylation. The dynamics of this process. 

Cresol red Crystal Violet Malachite Green Methanil Yellow Thymol Blue Orange IV -2,4-Dinitrophenol -Erythrosin, Na2 salt -Dimethyl Yellow Cl 11020 Bromophenol Blue Congo Red Cl 22120 Methyl Orange Bromocresol Green Alizarin Red S Cl 42750 Methyl Red Cl 13020 -Bromocresol Purple Chlorophenol Red p-Nitrophenol Alizarin Bromothymol Blue Brillant Yellow Phenol Red Neutral Red Cl 50040 -m-NItrophenol -Cresol Red Metacresol Purple Phenolphthalein -Thymolphthalein -P-Naphthyl Violet Alizarin Yellow R 2,4,6-T rinitrotoluene... 

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