33175-34-7

Usage

Synthesis Reference(s)

Journal of Medicinal Chemistry, 7, p. 665, 1964 DOI: 10.1021/jm00335a025

InChI:InChI=1/C6H5Cl2NO/c7-5-2-1-4(9-10)3-6(5)8/h1-3,9-10H

Upstream product

• 99-54-7 3,4-dichloronitrobenzene 
• 116278-64-9 C₁₁H₁₃Cl₂NO₂ 
• 823-86-9 N-(4-chlorophenyl)hydroxylamine 
• 95-76-1 m,p-dichloroaniline 

Downstream Products

• 67083-42-5 3,4-Dichloronitrosobenzene 
• 21232-47-3 3,3',4,4'-Tetrachloroazoxybenzene 
• 14063-31-1 (3,4-dichloro-phenyl)-hydroxy-thiocarbamic acid S-propyl ester 
• 14063-32-2 (3,4-dichloro-phenyl)-hydroxy-thiocarbamic acid S-isopropyl ester 
• 14063-33-3 N-(3,4-Dichlor-phenyl)-N-isobutylmercaptocarbonyl-hydroxylamin 
• 14063-30-0 N-(3,4-Dichlor-phenyl)-N-ethylmercaptocarbonyl-hydroxylamin 
• 75841-00-8 2-(3,4-Dichloro-phenyl)-5-hydroxy-5-methyl-isoxazolidin-3-one 
• 74491-46-6 N-(3,4-methylenedioxybenzylidene)-3,4-dichloroaniline N-oxide 
• 126614-96-8 3,4,4'-Trichloroazoxybenzene 
• 126614-95-7 3',4',4-Trichloroazoxybenzene 
• 106-47-8 4-chloro-aniline 
• 614-26-6 4,4'-bis(chloro)azoxybenzene 
• 823-86-9 N-(4-chlorophenyl)hydroxylamine 
• 86412-49-9 N-hydoxy-3,4-dichloroacetanilide 

Relevant academic research and scientific papers

Kinetics of the liquid-phase catalytic hydrogenation of chlorine-containing aromatic nitro compounds in the presence of pyridine

We have analyzed experimental kinetic data for nitro compound consumption, for the formation of the corresponding amino product, and for the accumulation of intermediate products and by-products in the hydrogenation of chlorine-containing aromatic nitro compounds. The reaction has been carried out under static conditions over a platinum catalyst on a porous support in the presence of pyridine. The effect of the admixture on different hydrogenation steps of a chlorine-containing aromatic nitro compound has been quantitatively interpreted.

3,4-Dichlorophenylhydroxylamine cytotoxicity in renal cortical slices from Fischer 344 rats

3,4-Dichlorophenylhydroxylamine (3,4-CPHA) is the N-hydroxyl metabolite of 3,4-dichloroaniline. 3,4-Dichloroaniline is a breakdown product of the herbicide Propanil. Previous work has shown that 3,4-dichloroaniline is acutely toxic to the kidney and bladder. The purpose of this study was to examine the in vitro toxicity of 3,4-dichlorophenylhydroxylamine. Renal cortical slices were prepared from male Fischer 344 rats (190-250 g) and were incubated with 0-0.5 mM 3,4-CPHA for 30-120 min under oxygen and constant shaking. 3,4-CPHA produced a concentration and time dependent alteration in lactate dehydrogenase (LDH) leakage, organic ion accumulation and pyruvate stimulated gluconeogenesis. Glutathione levels were diminished within 60 min below control values by 0.1 and 0.5 mM 3,4-CPHA. A 30 min pretreatment with 0.1 mM deferoxamine did not alter 3,4-CPHA toxicity. Alterations in pyruvate stimulated gluconeogenesis and LDH leakage were comparable between vehicle and deferoxamine pretreated tissues. Other studies examined the effect of (1 mM) glutathione, 2 mM ascorbic acid and 1 mM dithiothreitol (DTT) on toxicity. Pretreatment for 30 min with vehicle or 1 mM DTT induced comparable changes in LDH leakage and pyruvate stimulated gluconeogenesis. Pretreatment for 30 min with 1 mM glutathione or 2 mM ascorbic acid reduced 3,4-CPHA toxicity. LDH leakage was not elevated as markedly in renal slices pretreated with glutathione relative to slices pretreated with vehicle. These results indicate that 3,4-CPHA toxicity is through an iron independent mechanism. 3,4-CPHA cytotoxicity was reduced by pretreatment with glutathione or ascorbic acid suggesting formation of a reactive intermediate.

Liquid-phase catalytic hydrogenation of 3,4-dichloronitrobenzene over Pt/C catalyst under gradient-free flow conditions in the presence of pyridine

Experimental data on nitro compound uptake, the intermediate product accumulation, and the corresponding amine compound generation were obtained on hydrogenating 3,4-dichloronitrobenzene over Pt/C catalyst in the gradient-free flow regime in the presence and absence of pyridine. In addition, a side reaction of dehalogenation was investigated. The role of pyridine admixture on every step of the process was analyzed and the rate of hydrogenation of the nitro compound was determined both in the presence and in the absence of inhibitor.

Ultrasound-promoted highly chemoselective reduction of aromatic nitro compounds to the corresponding N-arylhydroxylamines using zinc and HCOONH 4 in CH3CN

N-Arylhydroxylamines were prepared in high yields through chemoselective reduction of the corresponding aromatic nitro compounds under ultrasound (59 kHz) at room temperature using a convenient Zn/HCOONH4/CH 3CN system. This method was highly efficient, environmentally benign, especially simple and practical. Copyright

Mechanism and reactivity in perborate oxidation of anilines in acetic acid

Perborate but not percarbonate in acetic acid generates peracetic acid on standing and the peracetic acid oxidation of anilines is fast. The oxidation with a fresh solution of perborate in acetic acid is smooth and second order but the specific oxidation rate increases with increasing [perborate]0 or [boric acid]. Perborate on dissolution affords hydrogen peroxide and a borate; the latter assists the former in the oxidation. The oxidation rates of anilines under identical conditions do not conform to any of the linear free energy relationships but the reaction rates of molecular anilines do. Perborate oxidation proceeds via two reaction paths but the overall oxidation rates of molecular anilines conform to structure reactivity relationships; the transition states do not differ significantly. Analysis of the oxidation rates of perborate and percarbonate reveals that while perborate oxidation is faster than percarbonate it is at least as selective as the latter.

Competitive Base-Induced α-Elimination and Methanolysis of N-Aryl-O-pivaloylhydroxylamines

The N-aryl-O-pivaloylhydroxylamines 1a-c are quite stable in MeOH under neutral conditions, but under mildly basic conditions (0.05 M Et2NH or Et3N) they undergo rapid decomposition (t1/2 = ca. 3-5 h at 25 deg C) by two competitive processes: apparent α-elimination to generate the nitrenes 2a-c and pivalic acid and basic ester methanolysis to generate the hydroxylamines 3a-c and methyl pivalate.The nitrenes decompose into the corresponding anilines 5 and azobenzenes 7, while the hydroxylamines undergo nitrene-mediated oxidation into the corresponding azoxybenzenes 6.The mechanism of this latter process was probed by addition of excess hydroxylamine, and a mechanism for the oxidation consistent with available data (Scheme II) is proposed.It was also found that the nitrosobenzenes 8 undergo nucleophilic attack by conjugate bases 4a-c of the title compounds to produce one of the two possible isomeric nonsymmetrical azoxybenzenes.

The Reaction between Cyanide Ion and Nitrones; a Novel Imidazole Synthesis

By contrast with the CN-diphenylnitrones, cold aqueous ethanolic potassium cyanide converts N-methyl-C-phenylnitrone into 1-methyl-4,5-diphenylimidazole.The scope of this reaction has been investigated, and shown to proceed via intermediate cyano-imines, some of which have been synthesised by alternative routes.