P-Chloro nitrobenzene

Chloro-5-nitrobenzene sulfonic acid is synthesized by addition of p-chloro-nitrobenzene as a melt to 20% Oleum (20% S03 in H2S04) at 100 °C [1], This is added over 20 minutes to Oleum heated at 50 °C. The temperature then rises to 120-125 °C due to the heat of reaction. The conversion is achieved by maintaining this temperature during several hours with 2 bar of steam. 

SYNS l-CHLOOR-4-NITROBENZEEN (DUTCH) 1-CHLOR-4-NITROBENZOL (GERMAN) p-CHLORO-NITROBENZENE 4-CHLORONITROBENZENE 1-CHLORO-4-NITROBENZENE 4-CHLORO-l-... 

The nitration of chlorobenzene with a mixed acid reagent comprising around 35% nitric acid, 53% sulfuric acid and 12% water, at temperatures of from 40 to 80 °C and a HNOa/chlorobenzene molar ratio of around 1 gives a 98% yield of an isomeric mixture consisting of around 33% o-chloronitrobenzene, 66% p-chloro-nitrobenzene and 1% m-chloronitrobenzene. 

Bray et al. (1957b) have summarized the metabolism of 19 mono-chloronitrobenzenes and related the lability of the displaced group in base hydrolysis to mercapturic acid formation. Thus, o and p-chloro-nitrobenzene produce small amounts of mercapturic acid by elimination of the chlorine the m-ch oronitrobenzene is not appreciably hydrolyzed and forms no mercapturic acid. Correspondingly, the ortho and para fluoro-, bromo-, and iodoiiitrobenzenes form considerable amounts of mercapturic acids (over 30% of the administered dose with fluoro- and o-bromo compounds) but the meta isomers formed none that could be isolated (Bray et al., 1953a). 

Wu J-f, C-y Jiang, B-j Wang, Y-f Ma, Z-p Liu, S-j Liu (2006) Novel partial reductive pathway for 4-chloro-nitrobenzene and nitrobenzene degradation in Comamonas sp. strain CNB-1. Appl Environ Microbiol 12 1759-1765. 

Synonyms AI3-15387 BRN 508691 CCRIS 142 l-Chloro-4-nitrobenzene 4-Chloronitro-benzene 4-Chloro-l-nitrobenzene p-Chloro-l-nitrobenzene EINECS 202-809-6 4-Nitrochlor-obenzene p-Nitrochlorobenzene 4-Nitrophenyl chloride p-Nitrophenyl chloride NSC 9792 PCNB PNCB UN 1578. 

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... 

Chloromethyl) oxhane, see Epichlorohydrin 2-(Chloromethyl)oxirane, see Epichlorohydrin 4-Chloro-3-methylphenol, see p-Chloro-ro-cresol p-Chloro-3-methylphenol, see p-Chloro-ro-cresol Chloromethyl phenyl ketone, see a-Chloroacetophenone p-Chloronaphthalene, see 2-Chloronaphthalene 4-Chloronitrobenzene, see p-Chloronitrobenzene l-Chloro-4-nitrobenzene, see p-Chloronitrobenzene 4-Chloro-l-nitrobenzene, seep-Chloronitrobenzene p-Chloro-1-nitrobenzene, see p-Chloronitrobenzene Chloronitroform, see Chloropicrin Chloronitropropane, see 1-Chloro-l-nitropropane Chlorophen, see Pentachlorophenol... 

Synonyms Benzene, 1-(chloromethyl-4-nitro- 1-Chloromethyl-4-nitrobenzene p-(Chloromethyl) nitrobenzene a-Chloronitrotoluene o-Chloro-4-nitrotoluene a-Chloro-p-nitrotoluene 4-Nitrobenzyl chloride Toluene, o-chloro-p-nitro-Empiricai C7H6CINO2... 

Propoxyethanol 2-(2>Methoxyethoxy)ethano p-Bromochlorobenzene p-Dibromobensene m-Chloro nitrobenzene o-Chloronitrobenzene p-Chloronitrobeniene o-Dichlorobensene p-Dichlorobensene Bromobensene o-Bromophenol Chlorobeniene p-Chlorophenol lodobencene Nitrobenzene o-Nitrophenol... 

Trinitrodipheny Isulfone, crysts (from glac acet ac), mp 196—97° was prepd by heating 4-chloro-rl,3-dinitrobenzene or 2,4-dinitrophenyl-p-toluenesulfonate with Na 3-nitrobenzene-l-sulfinate in aq ale (Refs 1 St 3) 3,5,4 TrinitrodiphenyIsulfone, ndls, mp 199° prepd by heating 3 nitrophenyI-(4-nitrophenyl)-sulfone with a mixt of fuming nitric acid 8c sulfuric acid at 150°(Refs 2St4)... 

Nitro-N,N-dipropylaniline, orn-yel, unpleasant acrid smelling oil, fr p — below solid CO2 temp, bp — dec on heating si sol in w sol in common org solvs. It was prepd by reacting 2-chloro-l-nitrobenzene dipropyl-amine in the presence of Cu powd in ale at 100°(Refs 1 St 4). It forms crystaddn salts, some of which are unstable ... 

Nitrobenzene-p-sulphonyI)neopine has been converted into the 6/3-chloro- and 6j0-bromo-6-deoxy-compounds by heating with lithium chloride and bromide,154 and the 6-O-methanesulphonyl analogue gives the same products together with the A6-8-deoxy-compound, which is the sole product when the ester is heated with sodium iodide.155 2-Nitromorphine and 2-nitrocodeine have been reduced to the 2-amino-compounds in 60% and 81% yield respectively.156... 

Table 9.7 contains recent data on the nitration of polychlorobenzenes in sulphuric acid. The data continue the development seen with the dichlorobenzenes. The introduction of more substituents into these deactivated systems has a smaller effect than predicted. Whereas the p-position in chlorobenzene is four times less reactive than a position in benzene, the remaining position in pentachlorobenzene is about four times more reactive than a position in 1,2,4,5-tetrachlorobenzene. The chloro substituent thus activates nitration, a circumstance recalling the fact that o-chloronitrobenzene is more reactive than nitrobenzene.426 As can be seen from table 9.7, the additivity principle does not work very well with these compounds, underestimating the rate of reaction of pentachlorobenzene by a factor of nearly 250, though the failure is not so marked in the other cases, especially viewed in the circumstance of the wide range of reactivities covered. 

Of the trimtro derivatives of chlorobenzene, l-chloro-2,4,6-nitrobenzene (m. p. 81.5-83°C), known also as picryl chloride, is the most important. Next in importance is l-chloro-2,4,5-trinitrobenzene (m. p. 116°C) ... 

GC-MS and HPLC analyses of electrolyzed solutions allowed the detection of aromatic intermediates such as p-benzoquinone and nitrobenzene for aniline, 4-chlorocatechol for 4-chlorophenol, 4-chlorophenol, 4-chlorocatechol, hydroquinone, and p-benzoquinone for 4-CPA, 4-chloro-o-cresol, mehylhy-droquinone, and methyl-p-benzoquinone for MCPA, 2,4-dichlorophenol, 4,6-dichlororesorcinol, chlorohydroquinone, and chloro-p-benzoquinone for 2,4-D, and 2,4,5-trichloro-phenol, 2,5-dichlorohydroquinone, 4,6-dichlororesorcinol, and 2,5-dihydroxy-p-benzoquinone for 2,4,5-T. In general, these by-products persisted in solution while the initial pollutant was degraded. 

Synonyms and trade names 4-chloronitrobenzene p-chloronitrobenzene PCNB PNCB p-nitrochlorobenzene l-chloro-4-nitrobenzene 4-nitro-chlorobenzene 4-chloronitrobenzene C6H4CINO2 (nitrobenzol, oil of mir-bane) nitrobenzene C6H5NO2 (nitrobenzol, oil of mirbane) o-nitrotolnene CH3C6H4NO2 (m-nitrotolnene, p-nitrotolnene)... 

---