347-91-1

Usage

Uses

Used in Pharmaceutical Industry:
2-(4-FLUOROPHENYL)ACETOPHENONE is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs with specific properties. The presence of the fluorine atom allows for unique transformations and reactions that can enhance the pharmacological activity of the resulting compounds.
Used in Agrochemical Industry:
In the agrochemical sector, 2-(4-FLUOROPHENYL)ACETOPHENONE serves as an intermediate in the production of agrochemicals, contributing to the development of effective pesticides and other agricultural chemicals. Its reactivity and the properties conferred by the fluorine atom make it a valuable component in the creation of compounds with targeted pest control capabilities.
Used in Organic Synthesis:
2-(4-FLUOROPHENYL)ACETOPHENONE is utilized as a reagent in organic synthesis for its potential to undergo various chemical transformations. This makes it a preferred starting material for the production of new compounds with specific characteristics, useful in a wide range of applications.
Used in Production of Fine Chemicals:
As a building block, 2-(4-FLUOROPHENYL)ACETOPHENONE is used in the manufacture of fine chemicals, where its unique structure and reactivity are leveraged to create high-quality specialty chemicals for diverse applications across different industries.

InChI:InChI=1/C14H11FO/c15-13-8-6-11(7-9-13)10-14(16)12-4-2-1-3-5-12/h1-9H,10H2

Upstream product

• 98-88-4 benzoyl chloride 
• 352-11-4 1-chloromethyl-4-fluorobenzene 
• 71-43-2 benzene 
• 405-50-5 p-Fluorophenylacetic acid 
• 459-04-1 4-Fluorophenylacetyl chloride 
• 532-27-4 1-chloroacetophenone 
• 352-13-6 4-flourophenylmagnesium bromide 
• 459-46-1 4-Fluorobenzyl bromide 
• 201230-82-2 carbon monoxide 
• 2522-81-8 2-<(2,2-dimethylpropanoyl)oxy>-1-phenylethanone 
• 1765-93-1 4-fluoroboronic acid 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 591-50-4 iodobenzene 
• 459-22-3 4-fluorophenylacetonitrile 

Downstream Products

• 73424-44-9 2-(4-Fluorphenyl)-1-phenyl-1-ethanon-p-tolylsulfonylhydrazon 
• 1443223-53-7 2-(4-fluorophenyl)-1-phenyl-2-p-tolylethanone 

Relevant academic research and scientific papers

H2O2-mediated room temperature synthesis of 2-arylacetophenones from arylhydrazines and vinyl azides in water

An environmentally benign, cost-efficient and practical methodology for the room temperature synthesis of 2-arylacetophenones in water has been discovered. The facile and efficient transformation involves the oxidative radical addition of arylhydrazines with α-aryl vinyl azides in the presence of H2O2 (as a radical initiator) and PEG-800 (as a phase-transfer catalyst). From the viewpoint of green chemistry and organic synthesis, the present protocol is of great significance because of using cheap, non-toxic and readily available starting materials and reagents as well as amenability to gram-scale synthesis, which provides an attractive strategy to access 2-arylacetophenones.

The organocatalytic enantiodivergent fluorination of β-ketodiaryl-phosphine oxides for the construction of carbon-fluorine quaternary stereocenters

Commercially available cinchona alkaloids that can catalyze the enantiodivergent fluorination of β-ketodiarylphosphine oxides were developed to construct carbon-fluorine quaternary stereocenters. This protocol features a wide scope of substrates and excellent enantioselectivities, and it is scalable.

Aerobic oxygenation of α-methylene ketones under visible-light catalysed by a CeNi3complex with a macrocyclic tris(salen)-ligand

A hetero-tetranuclear CeNi3 complex with a macrocyclic ligand catalysed the aerobic oxygenation of a methylene group adjacent to a carbonyl group under visible-light radiation to produce the corresponding α-diketones. The visible-light induced homolysis of the Ce-O bond of a bis(enolate) intermediate is proposed prior to aerobic oxygenation.

Iron-Catalyzed Enantioselective Radical Carboazidation and Diazidation of α,β-Unsaturated Carbonyl Compounds

Azidation of alkenes is an efficient protocol to synthesize organic azides which are important structural motifs in organic synthesis. Enantioselective radical azidation, as a useful strategy to install a C-N3 bond, remains challenging due to the inherently instability and unique structure of radicals. Here, we disclose an efficient enantioselective radical carboazidation and diazidation of α,β-unsaturated ketones and amides catalyzed by chiral N,N′-dioxide/Fe(OTf)2 complexes. An array of substituted alkenes was transformed to the corresponding α-azido carbonyl derivatives in good to excellent enantioselectivities, benefiting the preparation of chiral α-amino ketones, vicinal amino alcohols, and vicinal diamines. Control experiments and mechanistic studies proved the radical pathway in the reaction process. The DFT calculations showed that the azido transferred to the radical intermediate via an intramolecular five-membered transition state with the internal nitrogen of the Fe-N3 species.

Preparation method of aryl ketone

The invention discloses a preparation method of aryl ketone. The preparation method comprises the following steps: mixing a phenyl epoxy compound, aryl trifluoromethanesulfonate, a phosphine ligand, a nickel source, alkali and an organic solvent, and conducting reacting in one step under the protection of inert gas to generate aryl ketone. The preparation method disclosed by the invention is simple in process, mild in conditions and low in cost, and paves a way for large-scale industrial production application, such as drug synthesis or natural product synthesis application, of aryl ketone serving as an important organic reaction intermediate.

Palladium-catalyzed synthesis of α-aryl acetophenones from styryl ethers and aryl diazonium saltsviaregioselective Heck arylation at room temperature

Preparation of α-aryl acetophenones from styryl ethers and aryldiazonium salts is described. The reaction is catalyzed by palladium acetate at room temperature in the absence of ligand and base. The developed method is highly attractive in terms of reaction conditions, substrate scope, functional group tolerance and yields. Synthetic applications of the present method are demonstrated by preparing α-aryl indoles and 3-aryl isocoumarin from styryl ethers.

Ruthenium(II)-Catalyzed Cross-Coupling of Benzoyl Formic Acids with Toluenes: Synthesis of 2-Phenylacetophenones

Herein, we report a direct method to synthesize 2-phenylacetophenone through a ruthenium(II)-catalyzed cross-coupling reaction between acyl and benzyl radical. The various derivatives of 2-phenylacetophenone were prepared easily in moderate to good yields. These reactions provide a straightforward pathway to synthesize a variety of ketones bearing various functional groups.

Versatile and base-free copper-catalyzed α-arylations of aromatic ketones using diaryliodonium salts

A ligand and base-free copper catalyzed synthetic method for the efficient α-arylation of aromatic ketones is described. In order to avoid strong bases, ketone-derived silyl enol ethers were employed. Their reaction with diaryliodonium salts as aryl source provided the intermolecular C–C coupling displaying good functional group tolerance and requiring low catalyst loading.

Palladium-catalyzed denitrative α-arylation of ketones with nitroarenes

The palladium-catalyzed α-arylation of ketones with readily available nitroarenes and nitroheteroarenes provides access to useful α-aryl and α-heteroaryl ketones. The use of the Pd/ BrettPhos catalysts was critical to achieve high efficiency for these transformations, whereas other catalysts led to decreased yields or no conversions. The intramolecular type substrate was also applied in this methodology and gave a chromone derivative. Polyaromatic carbonyl compounds can be easily obtained by multicomponent tandem reactions, via nucleophilic aromatic substitution (SNAr) or cross-coupling reaction followed by this denitrative arylation. Kinetic experiments show that the electronic effect of nitrobenzenes has a greater effect on the reaction rate than the electronic effect of ketones.

1,2-Aryl Migration Induced by Amide C?N Bond-Formation: Reaction of Alkyl Aryl Ketones with Primary Amines Towards α,α-Diaryl β,γ-Unsaturated γ-Lactams

Rearrangement reactions incorporated into cascade reactions play an important role in rapidly increasing molecular complexity from readily available starting materials. Reported here is a Cu-catalyzed cascade reaction of α-(hetero)aryl-substituted alkyl (hetero)aryl ketones with primary amines that incorporates an unusual 1,2-aryl migration induced by amide C?N bond formation to produce a class of structurally novel α,α-diaryl β,γ-unsaturated γ-lactams in generally good-to-excellent yields. This cascade reaction has a broad substrate scope with respect to primary amines, allows a wide spectrum of (hetero)aryl groups to smoothly undergo 1,2-migration, and tolerates electronically diverse α-substituents on the (hetero)aryl ring of the ketones. Mechanistically, this 1,2-aryl migration may stem from the intramolecular amide C?N bond formation which induces nucleophilic migration of the aryl group from the acyl carbon center to the electrophilic carbon center that is conjugated with the resulting iminium moiety.