5798-71-0

Usage

Uses

Used in Organic Synthesis:
Ethanone, 1-(4-bromophenyl)-, oxime is used as a key intermediate in the synthesis of various organic compounds. Its reactivity with other chemicals allows for the creation of a wide range of new molecules, making it a valuable component in the field of organic chemistry.
Used in Pharmaceutical Research:
Ethanone, 1-(4-bromophenyl)-, oxime is used as a research tool in the development of new pharmaceuticals. Its unique chemical properties make it a promising candidate for the creation of novel drug molecules, potentially leading to the discovery of new treatments for various diseases and conditions.
Used in Pesticide Production:
Ethanone, 1-(4-bromophenyl)-, oxime is used as a starting material in the production of pesticides and other agricultural chemicals. Its chemical properties contribute to the effectiveness of these products, helping to protect crops and maintain agricultural productivity.
Used in Medicinal Chemistry:
Ethanone, 1-(4-bromophenyl)-, oxime is used as a building block in the design and synthesis of new medicinal compounds. Its potential applications in drug development make it an important resource for researchers working to create new and improved treatments for a variety of health issues.

Upstream product

• 99-90-1 para-bromoacetophenone 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 107093-06-1 1-(4-Bromo-phenyl)-1-hydroxyamino-ethanol 

Downstream Products

• 24358-62-1 1-(4-bromophenyl)ethylamine 
• 31709-50-9 3-(4-bromophenyl)isoxazolon-5(4H)-one 
• 23794-89-0 C₁₆H₁₂BrF₃N₂O₂ 
• 103-88-8 4-bromoacetanilide 
• 99-90-1 para-bromoacetophenone 
• 73568-35-1 6-bromo-2-chloro-3-formylquinoline 
• 79039-70-6 2-(4-bromophenyl)-6-chloro-4-(2-chlorophenyl)-quinoline 
• 73402-91-2 2-(4-bromophenyl)-4-phenylquinoline 
• 64222-40-8 1-vinyl-2-(4-bromophenyl)pyrrole 
• 4995-11-3 2-(4-bromophenyl)-1H-pyrrole 
• 3065-00-7 O--4-brom-acetophenonoxim 
• 177750-12-8 N-{1-(4-bromophenyl)vinyl}acetamide 
• 1068001-09-1 1-(4-bromophenyl)ethanone O-(2-hydroxy-3-phenoxypropyl)oxime 
• 1257846-36-8 1-methyl-3,4-diphenyl-6-bromo-isoquinoline 

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.

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(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.

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.).

Synthesis of 5-Vinyl-2-isoxazolines by Palladium-Catalyzed Intramolecular O-Allylation of Ketoximes

An efficient method for the synthesis of 5-vinyl-2-isoxazolines by Pd-catalyzed intramolecular O-allylation of ketoximes has been developed. The reaction involves Pd(0)-catalyzed π-allyl formation via leaving group ionization or Pd(II)-catalyzed allylic C-H activation followed by intramolecular nucleophilic oxime oxygen attack. This methodology has been elaborated to various value-added products by epoxidation, Wacker oxidation, cross-metathesis, hydroboration-oxidation, dihydroxylation, and catalytic hydrogenation.

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

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.

Chlorotropylium Promoted Conversions of Oximes to Amides and Nitriles

Chlorotropylium chloride as a catalyst for the transformations of oximes, ketones, and aldehydes to their corresponding amides and nitriles in excellent yields (up to 99 %) and in short reaction times (mostly 10–15 min). Oximes were electrophilically attacked on the hydroxyl oxygen by chlorotropylium. The produced tropylium oxime ethers were the key intermediates, of which the ketoxime ether led to amide through Beckmann rearrangement, and the aldoxime ether led to nitrile by nitrogen base DBU assisted formal dehydration. This chlorotropylium activation protocol offered general, mild, and efficient avenues bifurcately from oximes to both amides and nitriles by one organocatalyst.

Selective Dehydrogenative Acylation of Enamides with Aldehydes Leading to Valuable β-Ketoenamides

We have presented a unique example of dehydrogenative acylation of enamides with aldehydes enabled by an earth-abundant iron catalyst. The protocol provides the straightforward access to valuable β-ketoenamides with ample substrate scope and excellent functional group tolerance. Notably, distinct C-H acylation of enamide rather than at N-H moiety site occurs with absolute Z-selectivity was observed. Late-stage modifications of complex molecules and versatile synthetic utility of β-ketoenamides further highlight the practicability of this transformation.