2-chloro-4,6-dinitrophenol

The exothermicity and violence of the reaction of hydrazine hydrate with 1-chloro-2,4-dinitrophenol caused destruction of the reactor in which the reaction was carried out. This reaction is of the same kind as the previous one (2,4-dinitrophenylhydrazine preparation). 

Another example of the analogy between pyrazole and chlorine is provided by the alkaline cleavage of l-(2,4-dinitrophenyl)pyrazoles. As occurs with l-chloro-2,4-dinitrobenzene, the phenyl substituent bond is broken with concomitant formation of 2,4-dinitrophenol and chlorine or pyrazole anions, respectively (66AHC(6)347). Heterocyclization of iV-arylpyrazoles involving a nitrene has already been discussed (Section 4.04.2.1.8(i)). Another example, related to the Pschorr reaction, is the photochemical cyclization of (515) to (516) (80CJC1880). An unusual transfer of chlorine to the side-chain of a pyrazole derivative was observed when the amine (517 X = H, Y = NH2) was diazotized in hydrochloric acid and subsequently treated with copper powder (72TL3637). The product (517 X = Cl, Y = H) was isolated. 

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... 

VII. Preparation. There are two industrial methods of manufg PA 1) nitration of Phenol 2) nitration of dinitrophenol prepd by hydrolysis of chloro dinitrobenzene... 

The a- and /3-cyclodextrins have been found to accelerate the Smiles rearrangement of 4-nitrophenyl salicylate. The reaction of 2,4-dinitrobenzenesulfonamide with acyl chlorides in the presence of excess triethylamine has been found to produce the corresponding nitrile in good yield. Mechanistic studies have indicated that the reaction proceeds via a Smiles rearrangement of the initially formed iV-(2,4-dinitrobenzenesulfonyl)amide to form the nitrile, 2,4-dinitrophenol, and sulfur dioxide (see Scheme 12). l-Chloro-3-fluorophenothiazines have been prepared by Smiles rearrangement of 3-chloro-5-fluoro-2-formamido-2 -nitrophenyl sulfides in alcoholic... 

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... 

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. 

The nitration of both 4-methyl- and 4-chloro-2,6-dinitrotoluenes (66 and 67) with mixed acid in acetic acid at subambient temperature allows the isolation of the nitramines, (68) and (69), respectively. Thermolysis of (68) and (69) in refluxing methylene chloride yields the corresponding diazophenols, (70) and (71), respectively. Scilly and co-workers isolated 2-diazo-4,6-dinitrophenol (DINOL) (53) from the thermolysis of fV,2,3,5-tetranitroaniline (73) in ethyl acetate at 60 °C. 

Picryl fluoride undergoes nucleophilic attack by 3-nitrotriazol-5-one to give 3-nitro-l-picryl-triazol-5-one, a potential safe explosive <90JHC575>. This reaction does not occur with picryl chloride, 2-chloro-4,6-dinitrophenol being the unexplained product. 

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... 

Figure 8.9 The pH dependence of the /z-octanol-water distribution ratio of pentachlorophenol (PCP, pKj = 4.75), 4-chloro-a-(4-chlo-rophenyl) benzene acetic acid (DDA, pKb = 3.66), 2-methyl-4,6-dinitrophenol (DNOC, pKia = 4.46), and 2,4,5-trichlorophenoxy acetic acid (2,4,5-T, pKia = 2.83). (from Jafvert et al., 1990).

H2N(02N)2 C4H2. O.C6H,(N02 )2. Lemon-yel ndls(from AcOH or acet), mp 225—6° insol in w or in aq soda soln diff sol in ale, benz, chlf ligroin. Can be prepd by heating 3,5 dinitro-4-aminophenol with ale soln of 4-chloro-l,3 dinitrophenol. Its expl props were not investigated, although it is probably an p- l... 

In a 1-litre round-bottomed flask equipped with a reflux condenser place a solution of 62.5 g (0.6 mol) of anhydrous sodium carbonate in 500 ml of water and add 50 g (0.25 mol) of commercial l-chloro-2,4-dinitrobenzene. Reflux the mixture for 24 hours or until the oil passes into solution. Acidify the yellow solution with hydrochloric acid and, when cold, filter the crystalline dinitrophenol which has separated. Dry the product upon filter paper in the air. The yield is 42 g (91%). If the m.p. differs appreciably from 114°C, recrystallise from ethanol or from water. 

FIGURE 13.14 A typical LC-MS chromatogram obtained in the scan mode of a preconcentrated aqueous standard solution (a) and of a preconcentrated spiked river water sample (b), as well as of an unspiked preconcentrated river water sample (c). Peak labels denote Ph, Phenol 2,4-DMP, 2,4-dimethylphenol 2-CP, 2-chlo-rophenol 4-CR,4-chlorophenol 4-NP,4-nitrophenol 2-NP,2-nitrophenol 4-C-3-MP,4-chloro-3-methylphenol 2,4-DCP, 2,4-dichlorophenol 2,4-DNP, 2,4-dinitrophenol 2,4,6-TCP, 2,4,6-trichlorophenol 2-M-4.6-DNP, 2-methyl-4,6-dinitrophenol and PCP, pentachlorophenol. Spike level 1 pg/L 10 mL preconcentrated. 

S.W. Wilson, JRNBS 52, 195-99(1954) CA 48, 11061(1954)(A photoelectric colorimeter for measuring the chromaticities of pyrotechnic smokes) 20)Snell Snell 4(1954) [Colorimetric tests of various org compds including many expls and their primary materials, such as CarbazoIe(pp 314-15) Chloro-2,4-dinitrobenzene (p 17) 2,4-Dinittoanisole(p 19) Dinitrobenzene (p 16) Dinitrocresol(p 19) Dinitronaphthalene (p 19) Dinitrophenol(p 13) 2,4-Dinitroresorcinol (p 13) 2,4-Dinitrotoluene(p 18) Dinitroxylene ... 

A partial dearylation of diarylether during nitration had already been observed by Reilly, Drumm and Barrett [154], The dealkylation, observed by Schramm and Westheimer, has been confirmed by Ingold and his co-workers [152], For example p- chloroanisole, when nitrated with a 6N solution of nitric acid in the presence of acetic acid at 20°C gave 4-chloro-2-anisole in 66% yield and 4-chloro-2,6-dinitrophenol in 33% yield of theory. 

If the reaction is stopped just when the formation of chloropicrin starts, the presence of 6-chloro-2,4- and 4-chloro-2,6-dinitrophenols can be also detected along with it. 

Nowadays 2,4-dinitroaniline is prepared on a large scale by treating chloro-dinitrobenzene with ammonia. The method was first reported by Engelhardt and Lachinov [9] in 1870. Heating 2,4-dinitrophenol with an excess of urea at 208°C... 

A further instructive study on the influence of protic and dipolar aprotic solvents on the rate of SnI heterolysis of tertiary R3C-X (with X = Cl, Br, I, 2,4-dinitrophenolate) shows that the rate-accelerating anion solvation due to H-bonding by protic solvents decreases dramatically on increasing the radius of the halide ions. Therefore, the differential solvation transferred from anion-solvating methanol to cation-solvating dimethyl sulfoxide as solvent is reversed on going from the chloro- to the iodoalkane at 60 °C /ji(DMSO)/ki(MeOH) = 0.05 (t-BuCl) < 0.57 (t-BuBr) < 6.9 (t-BuI) the 2,4-dinitrophenolate ion behaves like the iodide [830]. 

Fig. 32.5 Influence of GC column internal diameter on separation 1. phenol 2. 2-chlorophenol 3. 2-nitrophenol 4. 2,4-dimethylphenol 5. 2,4-dichlorophenol 6. 4-chloro-3-methylphenol 7. 2,4,6-trichlorophenol 8. 2,4-dinitrophenol 9. 4-nitrophenol 10. 2-methyl-4,6-dinitrophenol 11. pentachlorophenol.

As in other nucleophilic substitutions, electron-withdrawing groups (NO2, CN, CO2H, SO3H) in ortho and para positions increase the reactivity of the aryl hahde to hydrolysis. For instance, chlorobenzene is best hydrolysed above 300 °C, whereas l-chloro-2,4-dinitrobenzene gives a 95% yield of 2,4-dinitrophenol at 100 °C . 

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