33175-34-7

Basic information

• Product Name: 3,4-dichloro-N-hydroxyaniline
• Synonyms: 3,4-dichloro-N-hydroxyaniline;3,4-dichlorophenylhydroxylamine;3,4-Dichlorophenylhydroxyamine;N-(3,4-Dichlorophenyl)hydroxylamine;Benzenamine, 3,4-dichloro-N-hydroxy-;Ccris 3010;Einecs 251-397-4
• CAS NO: 33175-34-7
• Molecular Formula: C₆H₅Cl₂NO
• Molecular Weight: 178.016
• EINECS: 251-397-4
• Mol File: 33175-34-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 75 °C (decomp)
• Boiling Point: 283.6°Cat760mmHg
• Flash Point: 125.3°C
• Appearance: /
• Density: 1.2549 (rough estimate)
• Vapor Pressure: 0.00147mmHg at 25°C
• Refractive Index: 1.5680 (estimate)
• PKA: 7.76±0.70(Predicted)
• CAS DataBase Reference: 3,4-dichloro-N-hydroxyaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-dichloro-N-hydroxyaniline(33175-34-7)
• EPA Substance Registry System: 3,4-dichloro-N-hydroxyaniline(33175-34-7)

Safety Data

• Hazardous Substances Data: 33175-34-7(Hazardous Substances Data)

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

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

Downstream Products

• 14063-32-2 (3,4-dichloro-phenyl)-hydroxy-thiocarbamic acid S-isopropyl ester 
• 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 
• 21232-47-3 3,3',4,4'-Tetrachloroazoxybenzene 
• 91631-60-6 N-sulfonoxy-3,4-dichloroacetanilide pyridinium salt 
• 75841-09-7 2-(3,4-Dichloro-phenyl)-5-methyl-isoxazol-3-one 
• 1160101-89-2 5,6-dichloro-3-phenylindole 
• 1160101-88-1 4,5-dichloro-3-phenylindole 
• 95-76-1 m,p-dichloroaniline 
• 51639-76-0 N-3',4'-dichlorophenyl-N-hydroxy-2-furancarboxamide 
• 53950-62-2 N-3,4-Dichlorphenyl-N-formylhydroxylamin 
• 86412-49-9 N-hydoxy-3,4-dichloroacetanilide 
• 126614-96-8 3,4,4'-Trichloroazoxybenzene 
• 126614-95-7 3',4',4-Trichloroazoxybenzene 

Relevant articles and documents

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.

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.

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.