823-86-9

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
4-chlorophenylhydroxylamine is used as a key intermediate in the synthesis of pharmaceuticals and agrochemicals for its ability to be incorporated into the molecular structures of these products, enhancing their efficacy and properties.
Used in Organic Chemistry:
4-chlorophenylhydroxylamine is used as a reagent in organic chemistry reactions due to its reactivity, facilitating the synthesis of other organic compounds.
Used in Antimicrobial and Antiviral Applications:
4-chlorophenylhydroxylamine has been studied for its potential biological activity and has been found to possess antimicrobial and antiviral properties, making it a candidate for use in applications targeting infectious diseases.

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

Upstream product

• 100-00-5 4-chlorobenzonitrile 
• 51639-68-0 N-(p-chlorophenyl)-2-furohydroxamic acid 
• 70-18-8 GLUTATHIONE 
• 33175-34-7 N-(3,4-dichlorophenyl)-hydroxylamine 
• 116278-63-8 N-(4-chlorophenyl)-O-pivaloylhydroxylamine 
• 1503-91-9 N-(4-chlorophenyl)-N-hydroxyacetamide 
• 1528-82-1 N-(4-chlorophenyl)benzohydroxamic acid 
• 131303-55-4 N-p-chlorophenylpicolinohydroxamic acid 
• 1303610-38-9 4-ClC₆H₄-N(Teoc)OTBS 
• 106-47-8 4-chloro-aniline 
• 109-89-7 diethylamine 
• 932-98-9 1-chloro-4-nitroso-benzene 
• 68166-12-1 N-p-chlorophenyl-2-thenohydroxamic acid 
• 163188-54-3 N-p-chlorophenyl-α-p-chlorophenylstyrylacrylohydroxamic acid 

Downstream Products

• 19865-58-8 N-(4-chlorophenyl)-α-phenylnitrone 
• 19865-61-3 N-(salicylidene)-4-chlorophenylamine-N-oxide 
• 109399-98-6 N,O-dibenzoyl-N-(4-chloro-phenyl)-hydroxylamine 
• 614-26-6 4,4'-bis(chloro)azoxybenzene 
• 1070874-61-1 cinnamaldehyde-[N-(4-chloro-phenyl)-oxime ] 
• 1602-00-2 bis-(4-chloro-phenyl)-diazene 
• 932-98-9 1-chloro-4-nitroso-benzene 
• 873-38-1 4-chloro-2-bromoaniline 
• 874-17-9 4-chloro-2,6-dibromoaniline 
• 554-00-7 2,4-Dichloroaniline 
• 61563-93-7 2-(4-chlorophenyl)-5-methylisoxazole-3(2H)-one 
• 27546-29-8 N'-Tosyloxy-N-<4-chlor-phenyl>-diimid-N-oxid 
• 3170-87-4 Iminokohlensaeure-<3-chlor-phenylester>-<4-chlor-phenylhydroxylamid> 
• 14063-23-1 N-(4-Chlor-phenyl)-N-ethylmercaptocarbonyl-hydroxylamin 

Relevant academic research and scientific papers

Selective Reduction of Nitroarenes to Arylamines by the Cooperative Action of Methylhydrazine and a Tris(N-heterocyclic thioamidate) Cobalt(III) Complex

We report an efficient catalytic protocol that chemoselectively reduces nitroarenes to arylamines, by using methylhydrazine as a reducing agent in combination with the easily synthesized and robust catalyst tris(N-heterocyclic thioamidate) Co(III) complex [Co(κS,N-tfmp2S)3], tfmp2S = 4-(trifluoromethyl)-pyrimidine-2-thiolate. A series of arylamines and heterocyclic amines were formed in excellent yields and chemoselectivity. High conversion yields of nitroarenes into the corresponding amines were observed by using polar protic solvents, such as MeOH and iPrOH. Among several hydrogen donors that were examined, methylhydrazine demonstrated the best performance. Preliminary mechanistic investigations, supported by UV-vis and NMR spectroscopy, cyclic voltammetry, and high-resolution mass spectrometry, suggest a cooperative action of methylhydrazine and [Co(κS,N-tfmp2S)3] via a coordination activation pathway that leads to the formation of a reduced cobalt species, responsible for the catalytic transformation. In general, the corresponding N-arylhydroxylamines were identified as the sole intermediates. Nevertheless, the corresponding nitrosoarenes can also be formed as intermediates, which, however, are rapidly transformed into the desired arylamines in the presence of methylhydrazine through a noncatalytic path. On the basis of the observed high chemoselectivity and yields, and the fast and clean reaction processes, the present catalytic system [Co(κS,N-tfmp2S)3]/MeNHNH2 shows promise for the efficient synthesis of aromatic amines that could find various industrial applications.

Electrochemically Tuned Oxidative [4+2] Annulation and Dioxygenation of Olefins with Hydroxamic Acids

This work represents the first [4+2] annulation of hydroxamic acids with olefins for the synthesis of benzo[c][1,2]oxazines scaffold via anode-selective electrochemical oxidation. This protocol features mild conditions, is oxidant free, shows high regioselectivity and stereoselectivity, broad substrate scope of both alkenes and hydroxamic acids, and is compatible with terpenes, peptides, and steroids. Significantly, the dioxygenation of olefins employing hydroxamic acid is also successfully achieved by switching the anode material under the same reaction conditions. The study not only reveals a new reactivity of hydroxamic acids and its first application in electrosynthesis but also provides a successful example of anode material-tuned product selectivity.

Practical bromination of arylhydroxylamines with SOBr2 towards ortho-bromo-anilides

A facile approach for synthesizing ortho-bromoanilides from readily available aryhydroxylamines and thionyl bromide is demonstrated in this work. Mild reaction conditions and broad scope of substrates ranging from heterocyclic structures to pharmaceutics-potential motifs are used in the reactions of this paper. Efficient bromination of ortho C–H bonds of the aryhydroxylamines has been achieved. Ortho-bromoanilide products were obtained in good to excellent yields, and model scaled-up reactions of this synthetic approach are shown in this work.

Synthesis, anti-microbial, toxicity and molecular docking studies of N-nitroso-N-phenylhydroxylamine (cupferron) and its derivatives

Bacterial resistance to antimicrobial agents is increasing at an alarming rate globally and requires new lead compounds for antibiotics. In this study, N-phenyl-N-nitroso hydroxylamine (cupferron) and its derivatives have been synthesised using readily available starting materials. The compounds were obtained in high yield and purity. They show activity towards a range of Gram-positive and Gram-negative pathogenic bacteria, with minimum inhibitory concentration (MIC) values as low as 2 μg.mL?1 against the tested organisms, especially for Gram-positive species. Toxicity studies on the lead compound 3b indicate insignificant effects on healthy cell lines. Molecular docking studies on the lead compound identify possible binding modes of the compound, and the results obtained correlate with those of in vitro and MIC studies. The lead compound shows excellent drug-likeness properties.

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.

Tandem selective reduction of nitroarenes catalyzed by palladium nanoclusters

We report a catalytic tandem reduction of nitroarenes by sodium borohydride (NaBH4) in aqueous solution under ambient conditions, which can selectively produce five categories of nitrogen-containing compounds: anilines, N-aryl hydroxylamines, azoxy-, azo- and hydrazo-compounds. The catalyst is in situ-generated ultrasmall palladium nanoclusters (Pd NCs, diameter of 1.3 ± 0.3 nm) from the reduction of Pd(OAc)2 by NaBH4. These highly active Pd NCs are stabilized by surface-coordinated nitroarenes, which inhibit the further growth and aggregation of Pd NCs. By controlling the concentration of Pd(OAc)2 (0.1-0.5 mol% of nitroarene) and NaBH4, the water/ethanol solvent ratio and the tandem reaction sequence, each of the five categories of N-containing compounds can be obtained with excellent yields (up to 98%) in less than 30 min at room temperature. This tunable catalytic tandem reaction works efficiently with a broad range of nitroarene substrates and offers a green and sustainable method for the rapid and large-scale production of valuable N-containing chemicals.

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.

Hydroxytriazene Derived from Sulphanilamide: Spectrophotometric and Biological Applications

In this investigation, we report synthesis, spectrophotometric application and antimicrobial activities of 3-hydroxy-3-(4-chlorophenyl)-1-(4- sulphonamido)phenyltriazene(HCNT) and its Fe(III) complex [Fe(HCNT)2(H2O)2]. The complex has been synthesized by traditional as well as mechanochemical routes.These compounds have been characterized and screened for antimicrobial activity against bacterial strains i.e. E. coli, S. aureus, S. pyogenes, P. aeruginosa and fungal strains i.e. A.clavatus, A. niger, C. albicans using brothmicrodilution method. The results indicate that the compounds may serve as better bactericides compared to fungicides and the molar composition of iron(III) complex was found 1:2 (Fe:HCNT) by spectrophotometric study.

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.