1956-39-4

Usage

Uses

Used in Organic Synthesis:
1-(4-CHLORO-PHENYL)-ETHANONE OXIME is used as a reagent in organic synthesis for the preparation of various nitrogen-containing compounds, contributing to the development of new chemical entities with potential applications in different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-(4-CHLORO-PHENYL)-ETHANONE OXIME is utilized as a key intermediate in the synthesis of drugs, playing a crucial role in the development of novel therapeutic agents.
Used in Agrochemical Industry:
1-(4-CHLORO-PHENYL)-ETHANONE OXIME is employed as a building block in the synthesis of agrochemicals, such as pesticides and herbicides, helping to improve crop protection and yield.
Used in Dye Industry:
In the dye industry, 1-(4-CHLORO-PHENYL)-ETHANONE OXIME is used for the preparation of dyes, contributing to the development of new colorants for various applications, including textiles, plastics, and printing inks.
Used in Metal Complex Chemistry:
1-(4-CHLORO-PHENYL)-ETHANONE OXIME serves as a ligand in metal complex chemistry, enabling the design and synthesis of metal complexes with potential applications in catalysis, materials science, and other areas.
Used as a Reagent for Detection of Aldehydes and Ketones:
1-(4-CHLORO-PHENYL)-ETHANONE OXIME is used as a reagent for the detection and identification of aldehydes and ketones, playing a vital role in analytical chemistry and quality control processes.

InChI:InChI=1/C8H8ClNO/c1-6(10-11)7-2-4-8(9)5-3-7/h2-5,11H,1H3/b10-6-

Upstream product

• 99-91-2 para-chloroacetophenone 
• 128381-43-1 1-(4-Chloro-phenyl)-ethanone O-(4,6-dimethyl-pyrimidin-2-yl)-oxime 
• 128381-47-5 1-(4-Chloro-phenyl)-ethanone O-(2,6-dimethyl-pyrimidin-4-yl)-oxime 
• 108-90-7 chlorobenzene 
• 75230-50-1 p-chloroacetophenone tosylhydrazone 
• 1073-67-2 4-vinylbenzyl chloride 
• 35588-60-4 p-chloro-(R,S)-1-phenylethylamine 

Downstream Products

• 109261-09-8 1-(4-chloro-phenyl)-ethanone-((E)-O-picryl oxime ) 
• 35588-60-4 p-chloro-(R,S)-1-phenylethylamine 
• 71516-65-9 1-(4-Chloro-phenyl)-ethanone O-[1-(4-chloro-phenyl)-eth-(E)-ylideneaminooxymethyl]-oxime 
• 25755-85-5 3-(4-chlorophenyl)isoxazol-5-(4H)-one 
• 60419-90-1 [3-(4-chloro-phenyl)-5-(4-fluoro-phenyl)-isoxazol-4-yl]-(4-fluoro-phenyl)-methanone 
• 14764-46-6 [3,5-bis-(4-chloro-phenyl)-isoxazol-4-yl]-(4-chloro-phenyl)-methanone 
• 23745-54-2 C₁₆H₁₂ClF₃N₂O₂ 
• 81963-65-7 2-(3-(4-chlorophenyl)isoxazol-5-yl)-1-phenylethan-1-one 
• 121505-66-6 1-(4-Chloro-phenyl)-ethanone O-{2-[1-(4-chloro-phenyl)-eth-(E)-ylideneaminooxy]-ethyl}-oxime 
• 128799-90-6 p-Chloroacetophenoxime Tosylate 
• 1236-90-4 2-(4-chlorophenyl)-4-phenylquinoline 
• 540485-24-3 P,P-diphenyl-N-[1-(4-chlorophenyl)ethylidene]phosphinic amide 

Relevant academic research and scientific papers

Polysubstituted Indole Synthesis via Palladium/Norbornene Cooperative Catalysis of Oxime Esters

Polysubstituted indoles are prevalent in pharmaceuticals, agrochemicals, and organic materials. Presented herein is the fact that polyfunctionalized indoles can be efficiently constructed from easily accessible oxime esters and aryl iodides, involving a palladium/norbornene synergistic synthesis. The reaction is enabled by a unique class of electrophiles in palladium/norbornene cooperative catalysis, which are oxime esters derived from simple ketone. The broad substrate scope and high functional group tolerance could make this method attractive for the synthesis of polysubstituted indoles.

Beckmann rearrangement of ketoximes promoted by cyanuric chloride and dimethyl sulfoxide under a mild condition

Synthesis of amides via Beckmann rearrangement of ketoximes promoted by cyanuric chloride (TCT)/DMSO under mild conditions has been reported. Conditions of the Beckmann rearrangement, e.g., solvents, the ratios of TCT/DMSO, and the temperature, were investigated using diphenylmethanone oxime as a substrate. The optimized conditions were adopted to afford fourteen amides with yields ranging from 20% to 99%. A plausible mechanism involving an active dimethyl alkoxysulfonium intermediate was proposed according to the mass spectrometry analysis. To our best knowledge, this is the first case of study on Beckmann rearrangement of ketoximes promoted by TCT/DMSO under a mild condition to afford amides efficiently.

AgNO3as Nitrogen Source for Cu-Catalyzed Cyclization of Oximes with Isocyanates: A Facile Route to N-2-Aryl-1,2,3-triazoles

A versatile copper-catalyzed [3 + 1 + 1] annulation of oximes and isocyanates with AgNO3 is described. In this conversion, AgNO3 and isocyanates instead of conventional azide or diazonium reagents were used as the nitrogen source. This three-component transformation was achieved by cleaving N-O/C-H/C-N bonds and building CN/N-N bonds, which provides a strategy to prepare N-2-aryl-1,2,3-triazoles with a good substrate and functional compatibility.

Rhodium(III)-Catalyzed Direct C-H Arylation of Various Acyclic Enamides with Arylsilanes

The stereoselective β-C(sp2)-H arylation of various acyclic enamides with arylsilanes via Rh(III)-catalyzed cross-coupling reaction was illustrated. The methodology was characterized by extraordinary efficacy and stereoselectivity, a wide scope of substrates, good functional group tolerance, and the adoption of environmentally friendly arylsilanes. The utility of this present method was evidenced by the gram-scale synthesis and further elaboration of the product. In addition, Rh(III)-catalyzed C-H activation is considered to be the critical step in the reaction mechanism.

Visible-light-promoted olefinic trifluoromethylation of enamides with CF3SO2Na

A visible-light-promoted olefinic C-H trifluoromethylation of enamides was developed by employing cheap and stable Langlois’ reagent as the CF3source. A series of β-CF3enamides were obtained in moderate to good yields with highE-isomer selectivity under mild conditions. Preliminary mechanistic studies suggest that molecular oxygen acts as the terminal oxidant for this net oxidative process, and theEisomer selectivity could be well explained by a base-assisted deprotonation of the cation intermediate.

Access to multi-functionalized oxazolines via silver-catalyzed heteroannulation of enamides with sulfoxonium ylides

Disclosed herein is an efficient Ag-catalyzed [4 + 1] heteroannulation reaction of enamides with α-carbonyl sulfoxonium ylides. The diastereoselective transformation provides a practical access to a diverse range of multi-functionalized oxazoline derivatives. The synthetic utility of the resultant tetra-substituted oxazolines is further demonstrated by a series of useful manipulations into valuable building blocks of pharmaceutical relevance.

Rhodium-Catalyzed C?H Activation/Annulation Cascade of Aryl Oximes and Propargyl Alcohols to Isoquinoline N-Oxides

A β-hydroxy elimination instead of common oxidization to carbonyl group in secondary propargyl alcohols was successfully developed to form 2-benzyl substituted isoquinoline N-oxides by a Rhodium-catalyzed C?H activation and annulation cascade, in which moderate to excellent yields (up to 92%) could be obtained under mild reaction conditions, along with good regioselectivity, broad generality and applicability. (Figure presented.).

Rhodium(iii)-catalyzed asymmetric [4+1] spiroannulations of: O -pivaloyl oximes with α-diazo compounds

Chiral RhIII catalysts can catalyze the asymmetric [4+1] spiroannulation of O-pivaloyl oximes with α-diazo homophthalimides under redox-neutral and acid/base-neutral conditions, leading to formation of chiral spirocyclic imines as a result of C-H activation and N-O cleavage. The reaction proceeded with high efficiency and features broad substrate scope, mild reaction conditions, and high to excellent enantioselectivities. This journal is

Dehydrative Beckmann rearrangement and the following cascade reactions

The Beckmann rearrangement has been predominantly studied for the synthesis of amide and lactam. By strategically using the in situ generated Appel's salt or Mitsunobu's zwitterionic adduct as the dehydrating agent, a series of Beckmann rearrangement and following cascade reactions have been developed herein. The protocol allows the conversion of various ketoximes into amide, thioamide, tetrazole and imide products in modular procedures. The generality and tolerance of functionalities of this method have been demonstrated.

C3-Arylation of indoles with aryl ketonesviaC-C/C-H activations

C3-Arylation of indoles with aryl ketones is accomplishedviapalladium-catalyzed ligand-promoted Ar-C(O) cleavage and subsequent C-H arylation of indole. Various (hetero)aryl ketones are compatible in this reaction, affording the corresponding 3-arylindoles in moderate to good yields. Further introduction of an indole moiety into the natural products desoxyestrone and evodiamine demonstrate the synthetic utility of this protocol.