10468-16-3

Basic information

• Product Name: 2-chlorophenylhydroxylamine
• Synonyms: 2-chlorophenylhydroxylamine;2-Chloro-N-hydroxyaniline;N-(2-chlorophenyl)hydroxylamine
• CAS NO: 10468-16-3
• Molecular Formula: C₆H₆ClNO
• Molecular Weight: 143.57
• Mol File: 10468-16-3.mol

Chemical Properties

• Boiling Point: 249 °C at 760 mmHg
• Flash Point: 104.4 °C
• Appearance: /
• Density: 1.409
• Vapor Pressure: 0.0124mmHg at 25°C
• Refractive Index: 1.661
• CAS DataBase Reference: 2-chlorophenylhydroxylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chlorophenylhydroxylamine(10468-16-3)
• EPA Substance Registry System: 2-chlorophenylhydroxylamine(10468-16-3)

Safety Data

• Hazardous Substances Data: 10468-16-3(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-chlorophenylhydroxylamine is used as a nucleophilic agent in various chemical reactions for the synthesis of a wide range of compounds. Its ability to react with electrophiles makes it a valuable intermediate in the production of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Laboratory Research:
In laboratory settings, 2-chlorophenylhydroxylamine serves as a key reagent in the study of organic reactions and mechanisms. Its unique properties allow researchers to explore its behavior in different chemical environments and understand the underlying principles of nucleophilic substitution and addition reactions.
Used in Industrial Applications:
2-chlorophenylhydroxylamine is utilized in various industrial applications, such as the manufacturing of dyes, pigments, and polymers, where its chemical properties contribute to the desired characteristics of the final products. Its reactivity and ability to form hydrogen bonds make it suitable for use in the development of new materials with specific properties.
Used in Analytical Chemistry:
Due to its reactivity and solubility in polar solvents, 2-chlorophenylhydroxylamine can be employed in analytical chemistry for the detection and quantification of certain compounds. Its ability to form complexes with specific analytes can be exploited for selective detection methods, such as spectrophotometry or chromatography.

InChI:InChI=1/C6H6ClNO/c7-5-3-1-2-4-6(5)8-9/h1-4,8-9H

Upstream product

• 88-73-3 2-Chloronitrobenzene 
• 71-43-2 benzene 
• 95-51-2 o-chloroaniline 

Downstream Products

• 13556-84-8 2,2'-dichloroazoxybenzene 
• 13556-84-8 2,2'-dichloroazoxybenzene 
• 19618-15-6 1-bromo-2-[(2-bromophenyl)-NNO-azoxy]benzene 
• 13556-84-8 2,2'-azoxychlorobenzene 
• 932-33-2 o-Chloronitrosobenzene 
• 134835-05-5 N-(3-Nitrocinnamoyl)-N-(2-chlorophenyl)hydroxylamine 
• 17609-80-2 4-amino-3-chlorophenol 
• 1020-39-9 N-(2-chlorophenyI)benzamide 
• 82344-31-8 N-(o-chlorophenyl)benzohydroxamic acid 
• 82344-32-9 N-(o-chlorophenyl)-acetohydroxamic acid 
• 172216-26-1 N-(2-Chloro-phenyl)-N-hydroxy-4-nitro-benzamide 
• 554-00-7 2,4-Dichloroaniline 
• 608-31-1 2,6-Dichloroaniline 
• 878561-52-5 C-(2-chlorophenyl)-N-(2-chlorophenyl)nitrone 

Relevant articles and documents

Shape-controlled synthesis and catalytic behavior of supported platinum nanoparticles

A 5 wt% Pt/C catalyst with around 20 nm cubic platinum particles was prepared through a conventional preparation method (i.e., precursor impregnation, reduction, and calcination) by choosing to use hydrophobic solvent in the impregnation procedure. The pr

Reaction pathways and the role of solvent in the hydrogenation of chloronitrobenzenes

Liquid phase hydrogenation of chloronitrobenzenes to corresponding chloroanilines over Pd on carbon (Pd/C) under mild reaction conditions was studied. On the basis of 1H, 13C NMR, GC-MS and HPLC analyses of reaction mixtures, the reaction pathways were evaluated. The reduction of substrates proceeds via the formation of chloronitrosobenzenes and N-(chlorophenyl)hydroxylamines and mainly results in the formation of the chloroanilines and aniline. Aniline is formed by hydrogenolysis of chlorine (dechlorination) in benzene ring. Other compounds (mono- and disubstituted azobenzenes and azoxybenzenes) were also detected by GS-MS and HPLC (3 mole %). The used solvent influences the reaction mixture composition and catalyst activity.

Factors determining the chemoselectivity of phosphorus-modified palladium catalysts in the hydrogenation of chloronitrobenzenes

The precursor nature effect on the state of the Pd–P surface layer in palladium catalysts and on their properties in the liquid-phase hydrogenation of chloronitrobenzenes under mild conditions has been investigated. A general feature of the Pd–P-containing nanoparticles obtained from different precursors and white phosphorus at P/Pd = 0.3 (PdCl2 precursor) and 0.7 (Pd(acac)2 precursor) is that their surface contains palladium in phosphide form (BE(Pd3d5/2) = 336.2 eV and BE(Р2р) = 128.9 eV) and Pd(0) clusters (BE(Pd3d5/2) = 335.7 eV). Factors having an effect on the chemoselectivity of the palladium catalysts in chloronitrobenzenes hydrogenation are considered, including the formation of small palladium clusters responsible for hydrogenation under mild conditions.

METHOD OF REDUCING AROMATIC NITRO COMPOUNDS

A method for reducing a substrate selected from 2-methyl-5-nitropyridine and methyl 4-(2-fluoro-3-nitrobenzyl)piperazine-1-carboxylate is provided catalysed by a nitroreductase and a disproportionation agent.

Selective Photoinduced Reduction of Nitroarenes to N-Arylhydroxylamines

We report the selective photoinduced reduction of nitroarenes to N-arylhydroxylamines. The present methodology facilitates this transformation in the absence of catalyst or additives and uses only light and methylhydrazine. This noncatalytic photoinduced transformation proceeds with a broad scope, excellent functional-group tolerance, and high yields. The potential of this protocol reflects on the selective and straightforward conversion of two general antibiotics, azomycin and chloramphenicol, to the bioactive hydroxylamine species.

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.

Highly Selective and Solvent-Dependent Reduction of Nitrobenzene to N-Phenylhydroxylamine, Azoxybenzene, and Aniline Catalyzed by Phosphino-Modified Polymer Immobilized Ionic Liquid-Stabilized AuNPs

Gold nanoparticles stabilized by phosphine-decorated polymer immobilized ionic liquids (AuNP@PPh2-PIILP) is an extremely efficient multiproduct selective catalyst for the sodium borohydride-mediated reduction of nitrobenzene giving N-phenylhydroxylamine, azoxybenzene, or aniline as the sole product under mild conditions and a very low catalyst loading. The use of a single nanoparticle-based catalyst for the partial and complete reduction of nitroarenes to afford three different products with exceptionally high selectivities is unprecedented. Under optimum conditions, thermodynamically unfavorable N-phenylhydroxylamine can be obtained as the sole product in near quantitative yield in water, whereas a change in reaction solvent to ethanol results in a dramatic switch in selectivity to afford azoxybenzene. The key to obtaining such a high selectivity for N-phenylhydroxylamine is the use of a nitrogen atmosphere at room temperature as reactions conducted under an inert atmosphere occur via the direct pathway and are essentially irreversible, while reactions in air afford significant amounts of azoxy-based products by virtue of competing condensation due to reversible formation of N-phenylhydroxylamine. Ultimately, aniline can also be obtained quantitatively and selectively by adjusting the reaction temperature and time accordingly. Introduction of PEG onto the polyionic liquid resulted in a dramatic improvement in catalyst efficiency such that N-phenylhydroxylamine could be obtained with a turnover number (TON) of 100000 (turnover frequency (TOF) of 73000 h-1, with >99% selectivity), azoxybenzene with a TON of 55000 (TOF of 37000 h-1 with 100% selectivity), and aniline with a TON of 500000 (TOF of 62500 h-1, with 100% selectivity). As the combination of ionic liquid and phosphine is required to achieve high activity and selectivity, further studies are currently underway to explore whether interfacial electronic effects influence adsorption and thereby selectivity and whether channeling of the substrate by the electrostatic potential around the AuNPs is responsible for the high activity. This is the first report of a AuNP-based system that can selectively reduce nitroarenes to either of two synthetically important intermediates as well as aniline and, in this regard, is an exciting discovery that will form the basis to develop a continuous flow process enabling facile scale-up.

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

Laccases for bio-bleaching

Provided herein are isolated laccase enzymes and nucleic acids encoding them. Also provided are mediators for laccase reactions. Also provided herein are methods for using laccases to oxidize lignins and other phenolic and aromatic compounds, such as for bio-bleaching and decolorization of wood pulp under high temperature and pH conditions to facilitate a substantial reduction in use of bleaching chemicals, as well as for treatment of fibers.