2- Nitro-5-chlorophenol

Chlorobenzene is converted mainly into m- chloronitrobenzene and o- chloro-phenol and 2-nitro-4-chlorophenol are also formed. 

C6Ds02f Resorcinol (a form), 46B, 97 C6Dg02, Resorcinol ip form), 46B, 97 CeHClsO, Pentachlorophenol, 27, 903 CsH2Cla02, Tetrachlorohydroquinone, 27, 901 32B, CeH3BrN205, 2-Bromo-4,6-dinitrophenol, 41B, 129 C6H3CIN2O5, 2-Chloro-4,6-dinitrophenol, 41B, 130 C6H, C1N03, 2-Nitro-4-chlorophenol, 42B, 85 C6H Cl20, 2,3-Dichlorophenol, 42B, 85... 

After drying for 10 min in a stream of cold air 1,4-phenylenediamine (h/Jj 5-10), 2-amino-4-chlorophenol (h/ f 15-20), 4-nitroaniline (h/ f 25-30) and l,4-amino-3-nitro-toluene (h/ f 50-55) appeared as blue-violet chromatogram zones on a blue background. These could be recognized without difficulty for several days from the back of the chromatogram. 

Polymers and resins Water purification, including removal of phenol, chlorophenols, ketones, alcohols, aromatics, aniline, indene, polynuclear aromatics, nitro- and chlor-aromatics, PCB, pesticides, antibiotics, detergents, emulsifiers, wetting agents, kraftmill effluents, dyestuffs recovery and purification of steroids, amino acids and polypeptides separation of fatty adds from water and toluene separation of aromatics from ahphatics separation of hydroquinone from monomers recovery of proteins and enzymes removal of colours from symps ... 

Uses Preparation of phenol, 4-chlorophenol, chloronitrobenzene, aniline, 2-, 3-, and 4-nitro-chlorobenzenes carrier solvent for methylene diisocyanate and pesticides solvent for paints insecticide, pesticide, and dyestuffs intermediate heat transfer agent. 

Irradiation of an aqueous solution at 296 nm and pH values from 8 to 13 yielded different products. Photolysis at a pH nearly equal to the dissociation constant (undissociated form) yielded pyrocatechol. At an elevated pH, 2-chlorophenol is almost completely ionized photolysis yielded cyclopentadienic acid (Boule et al., 1982). Irradiation of an aqueous solution at 296 nm containing hydrogen peroxide converted 2-chlorophenol to catechol and 2-chlorohydroquinone (Moza et al, 1988). In the dark, nitric oxide (10 vol %) reacted with 2-chlorophenol forming 4-nitro-2-chlorophenol and 6-nitro-2-chlorophenol at yields of 36 and 30%, respectively (Kanno and Nojima, 1979). 

The ARS Technologies, Inc., Ferox process is an in situ remediation technology for the treatment of chlorinated hydrocarbons, leachable heavy metals, and other contaminants. The process involves the subsurface injection and dispersion of reactive zero-valence iron powder into the saturated or unsaturated zones of a contaminated area. ARS Technologies claims that Ferox is applicable for treating the following chemicals trichloroethene (TCE), 1,1,1-trichloroethane (TCA), carbon tetrachloride, 1,1,2,2-tetrachloroethane, lindane, aromatic azo compounds, 1,2,3-trichloropropane, tetrachloroethene (PCE), nitro aromatic compounds, 1,2-dichloroethene (DCE), vinyl chloride, 4-chlorophenol, hexachloroethane, tribromomethane, ethylene dibromide (EDB), polychlorinated biphenyls (PCBs), Freon-113, unexploded ordinances (UXO), and soluble metals (copper, nickel, lead, cadmium, arsenic, and chromium). 

Hodson, P.V., R. PariseUa, B. Blunt, B. Gray, and K.L.E. Kaiser. 1991. Quantitative structure-activity relationships for chronic toxicity of phenol, p-chlorophenol, 2,4-dichlorophenol, pentachlorophenol, p-nitro-phenol and 1,2,4-trichlorohenzene to early life stages of the rainbow trout (Oncorhynchus mykiss). Canad. Tech. Rep. Fish. Aquat. Sci. 1784. 56 pp. 

The pH values of efficient extraction correspond to the pH range where the molecular form of the respective phenol dominates. The recovery of 4-nitro-phenol, 2,4-dinitrophenol, 2,6-dinitrophenol, 4-chlorophenol, 1-naphthol, and 2-naphthol is above 90% (the ratio of aqueous organic phase volume is 3 1). The extraction of naphthol and 4-chlorophenol is significant even at pH > pffa, more than 40 and 24% at pH > 10, respectively. Recovery of picric acid (2,4,6-trinitrophenol) is about 90% at pH 1.5-12.0, where the anionic form of picric acid dominates. Obviously, the high extraction is caused by high hydrophobicity of picrate anions. Recovery of the phenol itself and diatomic phenols, catechol and resorcinol is rather moderate (79,58, and 20%, respectively pH 1-7), which could be explained by relatively high hydrophi-licity of these compounds. 

Problem 19,14 Assign numbers from 1 for least to 4 for most to indicate the relative acid strengths in the following groups (a) phenol, m-chlorophenol, m-nitrophenol, m-cresol (b) phenol, benzoic acid, p-nitro-phenol, carbonic acid (c) phenol, p-chlorophenol, p-nitrophenol, p-cresol (d) phenol, o-nitrophenol, m-nitrophenol, p-nitrophenol (e) phenol, p-chlorophenol, 2,4,6-trichlorophenol, 2,4-dichlorophenol (/) phenol, benzyl alcohol, benzenesulfonic acid, benzoic acid. ... 

Trinitro-3-chlorophenol or Chloropicric Acid, yel crysts(AcOH or ale) or prisms(from w), mp 112-19°, not volatile with steam mod sol in chlf, benz, ale or eth can be obtd as the ultimate product of nitration of all mono- di-nitro-3-chlorophenols (Refs 2 3). It forms yel salts of Na, Ag, NH3 (mp 223 24 °) PhNH2 (mp 189 90°). See Refs 2, 3, 5,6, 7 8 for other props methods of prepn. The Chloride salt, an expl compd called Chloropicryl Chloride, is mentioned under Trinitrochloro-benzenes, Derivatives of Chlorobenzene... 

D. Puig, L. Silgoner, M. Grasserbauer and D. Barcelo, Part-per-trillion level determination of priority methyl-, nitro-, and chlorophenols in river water samples by automated onhne liquid/solid extraction followed by hquid chromatography/mass spectrometry using atmospheric pressure chemical ionization and ion spray interfaces , Anal. Chem. 69 2756-2761 (1997). 

Methyl, nitro and chlorophenols (EPA priority pollutants) LC-MS (atmospheric pressure chemical ionisation and ion spray interfaces) ppt [18]... 

Davis and his co-workers [127,128] found chlorobenzene also undergoes oxynitration by action of 65% nitric acid, with formation of trinitro-m-chlorophenol along with chlo-ronitrobenzenes, while naphthalene when nitrated with more dilute acid, for example, at a concentration of 65%, yielded 2,4-dinitro-a-naphthol besides 2-nitro-a-naphthol. 

The nitration reaction of chlorobenzene is usually accompanied by oxidation reactions, resulting in the formation of phenols, as for example, l-chloro-4-nitro-5-hydroxybenzene (2-nitro-5-chlorophenol) ... 

Chloro 6 nitro toluene bifenox, fomesafen, lactofen, perfluidone m-Chloro perbenzoic acid fipronil, rimsulfuron m-Chlorophenol cloprop, 3 CPA, oxyfluorfen... 

Fig. 5.2. ECD chromatogram of heptafluorobutyryl derivatives of phenols. Peaks 1 = phenol 2 = 4-chlorophenol 3 = 2-chlorophenol 4 = 2-bromophenol 5 = 2,4-dichlorophenol 6 = 2,6-dichloro-phenol 7 = p-rm.-butylphenol 8 = 2,4,6-trichlorophenol 9 = 2,4,5-trichlorophenol 10 = 2,4-di-bromophenol 11= o-phenylphenol. Conditions glass column, 270 cm X 2 mm I.D. nitro-DEGS bonded GC packing nitrogen flow-rate, 33 ml/min temperature, 80°C for 2 min, then programmed at 8°C/min to 170°C. Concentrations of phenols in the initial water sample ranged from 188 ppb (peak 7) to 44 ppb (peak 6). (Reproduced from J. Chromatogr., 156 (1978) 143, by courtesy of L.L. Lamparski.)...

The transformation of chlorophenols upon irradiation of nitrate mainly yields hydroxylated derivatives, while no nitration was observed. The absence of nitro derivatives can be attributed to the electron-withdrawing character of the chlorine atoms, inhibiting nitration. Dihydroxybenzenes and benzoquinone were also observed implying that a dechlorination process, induced by either hydroxyl or light, takes place in the system [123]. 

In addition to hydroxy-PCDEs, nitro- and aminoderivatives of PCDEs could be possible sources of PCDEs in the environment. Nitrofen is prepared by base-catalyzed condensation of 2,4-dichlorophenol (2,4-DCP) with l-chloro-4-nitrobenzene [30]. PCDEs have not been detected in 2,4-DCP and 2,4,5-TCP [37] but, in theory, just as the occurrence of PCDE by-products in chlorophe-nols is most likely due to the condensation of chlorophenols, the condensation of 2,4-dichlorophenol during the manufacture of nitrofen might lead to the formation of PCDEs. Aminofen is produced from nitrofen by catalytic reduction [4],... 

The American Water Work Association (AWWA) and US ERA developed a number of methods for phenol determination . ERA Method 528 is dedicated to the determination of phenols in drinking water by solid-phase extraction and GC/MS analysis and is developed for 12 phenols, mainly chlorophenols, nitro- and methyl-substituted phenols . Unfortunately, users have to take into account that the recommended internal standard tetrachlorophenol can also be found in water samples and has to be used with precaution or, better, substituted with another compound. The same problem applies in the case of the recommended surrogate 2,4,6-tribromophenol, which cannot be used in the analysis of water in areas with high bromine ion content. (Some examples of tribromophenol formation by humic or fulvic acid chlorination was mentioned by Richardson °°.)... 

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