10468-17-4

Usage

Uses

Used in Organic Chemistry:
N-(3-CHLORO-PHENYL)HYDROXYLAMINE is used as a reagent for its ability to react with different functional groups, such as ketones, aldehydes, and imines, to form oximes and hydrazones. This property makes it valuable in the synthesis of pharmaceuticals and agrochemicals.
Used in Pharmaceutical Synthesis:
N-(3-CHLORO-PHENYL)HYDROXYLAMINE is used as a precursor in the synthesis of various pharmaceutical compounds, contributing to the development of new medications.
Used in Agrochemical Synthesis:
Similarly, in the agrochemical industry, N-(3-CHLORO-PHENYL)HYDROXYLAMINE is used as a precursor for the synthesis of compounds that are integral to agricultural products.
Used as a Reducing Agent:
In certain chemical reactions, N-(3-CHLORO-PHENYL)HYDROXYLAMINE is utilized as a reducing agent, playing a crucial role in facilitating specific chemical transformations.
Safety Precautions:
When handling N-(3-CHLORO-PHENYL)HYDROXYLAMINE, it is important to take necessary safety measures to avoid skin and eye irritation, as well as to prevent ingestion or inhalation, due to its potential harmful effects.

Upstream product

• 932-78-5 1-chloro-3-nitrosobenzene 
• 67055-91-8 N-(m-Chlorophenyl)benzohydroxamic acid 
• 131303-57-6 N-m-chlorophenylpicolinohydroxamic acid 
• 51639-70-4 N-m-chlorophenyl-2-furohydroxamic acid 
• 78181-58-5 N-m-chlorophenyl-2-thenohydroxamic acid 
• 131303-58-7 N-m-chlorophenylquinaldinohydroxamic acid 
• 108-42-9 3-chloro-aniline 
• 107-91-5 cyanoacetic acid amide 
• 70-18-8 GLUTATHIONE 
• 121-73-3 3-Nitrochlorobenzene 

Downstream Products

• 139-24-2 3,3'-dichloroazoxybenzene 
• 932-78-5 1-chloro-3-nitrosobenzene 
• 28266-71-9 (3-chloro-phenyl)-hydroxy-carbamic acid ethyl ester 
• 14063-17-3 (3-chloro-phenyl)-hydroxy-thiocarbamic acid S-propyl ester 
• 14063-18-4 N-(m-Chlor-phenyl)-N-(isopropyl-mercaptocarbonyl)-hydroxylamin 
• 14063-20-8 N-(3-Chlor-phenyl)-N-isobutylmercaptocarbonyl-hydroxylamin 
• 14063-19-5 N-(3-Chlor-phenyl)-N-butylmercaptocarbonyl-hydroxylamin 
• 14063-22-0 N-(3-Chlor-phenyl)-N-pentylmercaptocarbonyl-hydroxylamin 
• 14063-16-2 N-(3-Chlor-phenyl)-N-ethylmercaptocarbonyl-hydroxylamin 
• 14063-15-1 N-(3-Chlor-phenyl)-N-methylmercaptocarbonyl-hydroxylamin 
• 121399-11-9 N-m-chlorophenyl-2-furylacrylohydroxamic acid 
• 79691-62-6 4a-hydroxy-6-(m-chlorophenyl)quinuclidino<4,5-b>isoxalidine 
• 3964-52-1 2-chloro 4-aminophenol 
• 67055-91-8 N-(m-Chlorophenyl)benzohydroxamic acid 

Relevant academic research and scientific papers

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

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.

Selective hydrogenation of nitroaromatics to: N -arylhydroxylamines in a micropacked bed reactor with passivated catalyst

In this contribution, a protocol was established for the selective catalytic hydrogenation of nitroarenes to the corresponding N-arylhydroxylamines. The reduction of 1-(4-chlorophenyl)-3-((2-nitrobenzyl)oxy)-1H-pyrazole, an intermediate in the synthesis of the antifungal reagent pyraclostrobin that includes carbon-chlorine bonds, benzyl groups, carbon-carbon double bonds and other structures that are easily reduced, was chosen as the model reaction for catalyst evaluation and condition optimization. Extensive passivant evaluation showed that RANEY-nickel treated with ammonia/DMSO (1 : 10, v/v) afforded the optimal result, especially with a particle size of 400-500 mesh. To combine the modified catalyst with continuous-flow reaction technology, the reaction was conducted at room temperature, rendering the desired product with a conversion rate of 99.4% and a selectivity of 99.8%. The regeneration of catalytic activity was also studied, and an in-column strategy was developed by pumping the passivate liquid overnight. Finally, the generality of the method was explored, and 7 substrates were developed, most of which showed a good conversion rate and selectivity, indicating that the method has a certain degree of generality.

A general and scalable synthesis of polysubstituted indoles

A consecutive 2-step synthesis of N-unprotected polysubstituted indoles bearing an electron-withdrawing group at the C-3 position from readily available nitroarenes is reported. The protocol is based on the [3,3]-sigmatropic rearrangement of N-oxyenamines generated by the DABCO-catalyzed reaction of N-arylhydroxylamines and conjugated terminal alkynes, and delivers indoles endowed with a wide array of substitution patterns and topologies.

Regioselective installation of fluorosulfate (-OSO2F) functionality into aromatic C(sp2)-H bonds for the construction of: Para-amino-arylfluorosulfates

The construction of para-amino-arylfluorosulfates was achieved through installation of fluorosulfate (-OSO2F) functionality into aromatic C(sp2)-H bonds by the reaction of N-arylhydroxylamine with sulfuryl fluoride (SO2Fs

Influence of the side-group at C=N bridging bond of bis-aryl Schiff bases on the wavelength of absorption maximum of ultraviolet absorption spectra

The compounds N-(benzylidene)-anilines XArCH=NArY (XBAY), N-(phenyl-ethylene)-anilines XArC(CH3)=NArY (XPEAY) and N-phenyl-α-phenylnitrones XArCH=N(O)ArY (XPNY) have bridging group CH=N, C(CH3)=N and CH=N(O) respectively, in which the C(CH3)=N has a side-group methyl CH3 at carbon end and the CH=N(O) has a side-group O atom at nitrogen end. In this work, a series of XPEAY and XPNY were synthesized, and their longest wavelength maximum λmax (nm) of ultraviolet absorption spectra were measured. Then the change regularity of the νmax (cm-1, νmax=1/λmax) of XPEAY and XPNY were investigated, and they were compared with that of XBAY (reported by ref.26). The results indicate: (1) There are no good linear relationships between the νmax of XBAYs and XPEAYs or XPNYs. (2) In case of a same set of X-Y group couples, the distribution of λmax of XPEAYs is larger than that of XPNYs. (3) The side-group CH3 makes the effect of σ(X) larger than that of σ(Y) on the νmax of XPEAYs, whereas the O atom makes the effect of σ(Y) larger than that of σ(X) on the νmax of XPNYs. (4) The cross-interaction between X and Y has important effect on the all νmax. However, the cross-interaction between CH3 and X/Y has not important effect on the νmax of XPEAY, and the cross-interaction between O and X/Y has not important effect on the νmax of XPNY. Copyright

An asymmetric pericyclic cascade approach to 3-alkyl-3-aryloxindoles: Generality, applications and mechanistic investigations

The reaction of L-serine derived N-arylnitrones with alkylarylketenes generates asymmetric 3-alkyl-3-aryloxindoles in good to excellent yields (up to 93%) and excellent enantioselectivity (up to 98% ee) via a pericyclic cascade process. The optimization, scope and applications of this transformation are reported, alongside further synthetic and computational investigations. The preparation of the enantiomer of a Roche anti-cancer agent (RO4999200) 1 (96% ee) in three steps demonstrates the potential utility of this methodology.

Rhodium(III)-catalyzed internal oxidative coupling of N-hydroxyanilides with alkenes via C-H activation

Abstract Described herein is an efficient new method for ortho-olefination of anilides in the presence of AgSbF6 and NaOAc via rhodium(III)-catalyzed internal oxidative C-H bond activation based on hydroxyl as directing and oxidative group. A range of alkenes and functional groups on acetanilides is supported and a possible mechanism is proposed according to the experimental results.

Solid supported platinum(0) nanoparticles catalyzed chemo-selective reduction of nitroarenes to N-arylhydroxylamines

Solid supported platinum(0) (SS-Pt) nanoparticles were developed as a heterogeneous catalyst following a reduction/deposition method and characterized by SEM, TEM, EDX and XRD analysis. The SS-Pt catalyst was applied in the chemo-selective reduction of nitroarenes to N-arylhydroxylamines using hydrazine hydrate as a hydrogen source. A wide variety of reducible functional groups such as halides, carboxylic acids, esters, amides, nitriles, keto, alkenes, alkynes and N-benzyl were well tolerated under the reaction conditions. This process was further successfully employed in 10 g scale reactions. N-Arylhydroxylamines were further applied for catalyst free synthesis of azoxybenzenes. Moreover, use of PEG-400 as cheap reaction medium, additive free methodology and the recyclability of SS-Pt catalyst up to ten times without significant loss of catalytic activity evidently follow the principles of green chemistry.

Selective reduction of nitroarenes to N-arylhydroxylamines by use of Zn in a CO2-H2O system, promoted by ultrasound

The promoting effect of ultrasound on the selective reduction of nitroarenes to N-arylhydroxylamines by use of Zn in an environmentally benign CO2-H2O system has been demonstrated. The yield of N-phenylhydroxylamine reaches 95% when the reaction is carried out with a Zn-to-nitrobenzene molar ratio of 2.2 under ultrasound (40 kHz) at 25 °C and normal pressure of CO2 for 60 min. Application of ultrasound to the reaction has the advantages of higher yield of N-arylhydroxylamines, shorter reaction time, and consumption of less Zn. Springer Science+Business Media B.V. 2012.