75841-13-3

Basic information

• Product Name: Benzenamine, 3,5-dichloro-N-hydroxy-
• CAS NO: 75841-13-3
• Molecular Formula: C6H5Cl2NO
• Molecular Weight: 178.018
• Mol File: 75841-13-3.mol

Chemical Properties

• CAS DataBase Reference: Benzenamine, 3,5-dichloro-N-hydroxy-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenamine, 3,5-dichloro-N-hydroxy-(75841-13-3)
• EPA Substance Registry System: Benzenamine, 3,5-dichloro-N-hydroxy-(75841-13-3)

Safety Data

• Hazardous Substances Data: 75841-13-3(Hazardous Substances Data)

Upstream product

• 618-62-2 3,5-dichloro-1-nitrobenzene 

Downstream Products

• 75841-01-9 2-(3,5-Dichloro-phenyl)-5-hydroxy-5-methyl-isoxazolidin-3-one 
• 75841-10-0 2-(3,5-Dichloro-phenyl)-5-methyl-isoxazol-3-one 
• 75841-07-5 2-(3,5-Dichloro-phenyl)-5-methoxy-5-methyl-isoxazolidin-3-one 
• 1388721-40-1 3-(3,5-dichlorophenyl)-2-oxa-3-azabicyclo[2.2.2]oct-5-ene 

Relevant articles and documents

Trifluoromethyl Vinyl Sulfide: A Building Block for the Synthesis of CF3S-Containing Isoxazolidines

Trifluoromethyl vinyl sulfide, a potential building block for pharmaceutically and agrochemically relevant products, is prepared and used for the first time in high-pressure-mediated 1,3-dipolar cycloaddition reactions with nitrones to synthesize (trifluoromethyl)sulfanyl isoxazolidines.

Reaction of arylhydroxylamines with [Pd(Neoc)(NO3)2] (Neoc = neocuproine). Non-innocent behavior of the nitrate anion

In an effort to understand the first stages of the reduction of nitroarenes to anilines by palladium/phenanthroline complexes and suspecting that arylhydroxylaminato complexes may be intermediates in this process, we investigated the reactivity of [Pd(Neoc)(NO3)2] (Neoc = neocuproine = 2,9-dimethyl-1,10-phenanthroline) with 3,5-dichlorophenylhydroxylamine. Spectroscopic evidence indicates that the desired [Pd(Neoc)(ONHC6H3Cl2)(NO3)] is indeed formed, but the complex is not stable and decomposes within a few hours. Two of the decomposition products were characterized by single crystal X-ray diffraction. They are a N-aryl-N-nitrosohydroxylaminato complex, [Pd(Neoc)(ON(3,5-C6H3Cl2)NO)][NO3] (major decomposition product) and a nitro-nitrate complex [Pd(Neoc)(NO2)(NO3)]. The results indicate that the nitrate ion is not innocent in the starting complex and oxidize hydroxylamine, being reduced itself to NO2? and NO.

Polystyrene stabilized iridium nanoparticles catalyzed chemo- and regio-selective semi-hydrogenation of nitroarenes to N-arylhydroxylamines

Polystyrene stabilized Iridium (Ir@PS) nanoparticles (NPs) as a heterogeneous catalyst have been developed and characterized by IR, UV–Vis, SEM, TEM, EDX and XRD studies. The prepared Ir@PS catalyst showed excellent reactivity for chemo- and regio-selective controlled-hydrogenation of functionalized nitroarenes to corresponding N-arylhydroxylamine using hydrazine hydrate as reducing source and environmentally benign polyethylene glycol (PEG-400) as green solvent. The present methodology was applied for vast substrate scope and found to be compatible with wide range of reducible functional groups. The reaction performed at 85 °C or ambient temperature and completed within 5–80 minutes. The catalyst can easily be filtered out from reaction mixture and reusable.

Polyfunctionalized biaryls accessed by a one-pot nucleophilic aromatic substitution and sigmatropic rearrangement reaction cascade under mild conditions

A practical synthetic method has been developed for polyfunctionalized biaryls based on a facile one-pot nucleophilic aromatic substitution (SNAr) reaction and [5,5]- or [3,3]-sigmatropic rearrangement reaction cascade. Under mild basic conditions, N-arylhydroxylamines reacted with o-activated fluoro (het)arenes to form N,O-diarylhydroxylamine intermediates which underwent spontaneously selective [5,5]-sigmatropic rearrangement reaction to produce diverse functionalized 4-amino-4′-hydroxy-1,1′-biaryls. A sequential SNAr reaction and [3,3]-sigmatropic rearrangement took place between N-arylhydroxylamines and 2-fluoropyridine derivatives or 4-fluorobenzonitrile to afford functionalized 2-amino-2′-hydroxy-1,1′-biaryls. As invaluable and unique building blocks, the resulting biaryls were applied in the straightforward synthesis of N2,O2-coronarene, carbazole, aza- and diaza carbazole derivatives.

Rapid Access to Fluorinated Anilides via DAST-Mediated Deoxyfluorination of Arylhydroxylamines

A new strategy for the synthesis of fluorinated anilides in the absence of metals and oxidants has been developed. This deoxyfluorination of N-arylhydroxylamines with diethylaminosulfur trifluoride (DAST) proceeded smoothly under mild conditions, and the

Ultrasonically activated reduction of substituted nitrobenzenes to corresponding N-arylhydroxylamines

Arylhydroxylamines can be obtained by reduction of the corresponding nitroaromatic compounds. We report here an efficient preparation of arylhydroxylamines by a controlled reduction of nitro compounds using zinc metal and ammonium chloride under ultrasonic activation in very short reaction times.