403-42-9

Usage

Chemical Properties

Clear colorless to slightly yellow liquid

Uses

Different sources of media describe the Uses of 403-42-9 differently. You can refer to the following data:
1. 4’Fluoroacetophenone is an intermediate used for the synthetic preparation of various pharmaceutical good and agricultural products.
2. 4-Fluoroacetophenone can be used as organic synthesis intermediates and pharmaceutical intermediates, mainly used in laboratory research and development processes and chemical production processes.
3. 4’-Fluoroacetophenone is an intermediate used for the synthetic preparation of various pharmaceutical good and agricultural products.

Synthesis

General procedure: Oximes (1.0 mmol), Amberlyst-15 (0.02 g), FPA53-NO2(0.02 g), and solvent (1.5 mL) were introduced into a 25-cm-high, 90-mL autoclave with a glass tube inside equipped with magnetic stirrer (Scheme 2). Then the autoclave was charged with oxygen to 0.1 MPa. The reaction mixture was stirred at desirable temperature for special time. Progress of the reaction was monitored by thin-layer chromatography (TLC) or gas chromatography (GC). After the reaction, the resin (Amberlyst-15 and FPA53-NO2) was separated from the reaction mixture by filtration and extracted with 3 mL CH3CN (2 1.5 ml). The solvent was removed under reduced pressure. The residue was further purified by column chromatography on silica gel (300 mesh) with hexane/ethyl acetate to give the corresponding carbonyl compounds.

Upstream product

• 403-41-8 1-(4-Fluorophenyl)ethanol 
• 462-06-6 fluorobenzene 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 60-29-7 diethyl ether 
• 352-13-6 4-flourophenylmagnesium bromide 
• 75-05-8 acetonitrile 
• 75-75-2 methanesulfonic acid 
• 87261-60-7 N-(4-acetylphenylazo)piperidine 
• 98516-45-1 (4-acetyl-phenyl)-dimethyl sulfonium ; methyl sulfate 
• 86452-55-3 1-(p-acetophenyl)-3,3-diethyl-1-triazene 
• 766-98-3 1-ethynyl-4-fluorobenzene 
• 64-19-7 acetic acid 
• 403-29-2 2-bromo-4'-fluoroacetophenone 

Downstream Products

• 582-70-7 1-(4-fluoro-phenacyl)-pyridinium; iodide 
• 1543-31-3 6-fluoro-2-(4-fluorophenyl)quinoline-4-carboxylic acid 
• 446-94-6 7-chloro-2-(4-fluoro-phenyl)-quinoline-4-carboxylic acid 
• 441-28-1 2-(4-fluorophenyl)-quinoline-4-carboxylic acid 
• 391-23-1 6-bromo-2-(4-fluoro-phenyl)-quinoline-4-carboxylic acid 
• 582-65-0 1-(4-fluorophenyl)-4,4,4-trifluoro-1,3-butanedione 
• 22966-25-2 (E)-1-(4-fluorophenyl)-3-phenyl-2-propen-1-one 
• 126443-11-6 4'-fluoro-4-methoxy-trans-chalcone 
• 339-23-1 1-(4-fluorophenyl)-1-phenylethan-1-ol 
• 565-31-1 2-(4-fluorophenyl)-2-methyl-1,3-dithiolane 
• 451-29-6 4,4,4-trichloro-1-(4-fluorophenyl)-3-hydroxybutan-1-one 
• 2805-55-2 2,4'-difluoro-trans-chalcone 
• 3792-93-6 (E)-1-(4-fluorophenyl)-3-(2-nitrophenyl)prop-2-en-1-one 
• 459-47-2 1-ethyl-4-fluorobenzene 

Relevant academic research and scientific papers

Mesoporous Silica Supported Au Nanoparticles with Controlled Size as Efficient Heterogeneous Catalyst for Aerobic Oxidation of Alcohols

A series of Au catalysts with different sizes were synthesized and employed on amine group functionalized ordered mesoporous silica solid supports as catalyst for the aerobic oxidation of various alcohols. The mesoporous silica of MCM-41 supported Au nano

Structure-Guided Evolution of Aryl Alcohol Oxidase from Pleurotus eryngii for the Selective Oxidation of Secondary Benzyl Alcohols

Aryl alcohol oxidase (AAO) is a fungal flavoenzyme capable of oxidizing aromatic primary alcohols into their correspondent aldehydes through a stereoselective hydride abstraction. Unfortunately, this enzyme does not act on secondary benzyl alcohols in racemic mixtures due to the strict control of substrate diffusion and positioning at the active site restricted to primary benzyl alcohols. Here we describe the engineering of AAO from Pleurotus eryngii to oxidize chiral benzyl alcohols with high enantioselectivity. The secondary benzyl alcohol oxidase was remodeled at the active site through four cycles of structure-guided evolution, including a final step of in vivo site-directed recombination to address the positive epistatic interactions between mutations. The final variant, with five substitutions and a renovated active site, was characterized at biochemical and computational level. The mutational sculpting helped position the bulkier (S)-1-(p-methoxyphenyl)-ethanol, improving the mutant's catalytic efficiency by three orders of magnitude relative to the native enzyme while showing a high enantioselectivity (ee >99%). As a promising candidate for racemic resolution, this evolved secondary benzyl alcohol oxidase maintained its natural stereoselective mechanism while displaying activity on several secondary benzyl alcohols. (Figure presented.).

Efficient oxidation of benzylic alcohols with trichloroisocyanuric acid and ionic liquid in water

A new environmentally friendly method for oxidation of benzylic alcohols to aldehydes or ketones has been developed using trichloroisocyanuric acid and [bmim]BF4 in water.

Visible light-mediated, high-efficiency oxidation of benzyl to acetophenone catalyzed by fluorescein

An environmentally friendly aerobic oxidation of benzyl C(sp3)-H bonds to ketones via selective oxidation catalysis was developed. Fluorescein is an efficient photocatalyst with excellent chemical selectivity. The reaction has a wide substrate scope, and a successful gram-scale experiment demonstrated its potential industrial utility.

Selective Activation of Unstrained C(O)-C Bond in Ketone Suzuki-Miyaura Coupling Reaction Enabled by Hydride-Transfer Strategy

A Rh(I)-catalyzed ketone Suzuki-Miyaura coupling reaction of benzylacetone with arylboronic acid is developed. Selective C(O)-C bond activation, which employs aminopyridine as a temporary directing group and ethyl vinyl ketone as a hydride acceptor, occurs on the alkyl chain containing a β-position hydrogen. A series of acetophenone products were obtained in yields up to 75%.

Ferric ion concentration-controlled aerobic photo-oxidation of benzylic C–H bond with high selectivity and conversion

A Fe(III)-promoted highly selective photo-oxidation of benzylic C–H bond delivering relative carbonyl products is reported. By altering the concentration of ferric salt, methylarenes can be selectively oxidized under UV irradiation to furnish aromatic aldehydes or acids, respectively. By this protocol, the oxidation of ethylarenes provides the corresponding acetophenones. The reaction is inferred to involve divergent pathways in different concentrations of catalyst for the alternative selectivity between aldehydes and aicds. The reusable catalyst, high conversion and selectivity make this oxidation a green and economic protocol for the synthesis of aromatic carbonyl compounds.

Visible-Light-Driven Selective Air-Oxygenation of C?H Bond via CeCl3 Catalysis in Water

Visible-light-induced C?H aerobic oxidation is an important chemical transformation that can be applied for the synthesis of aromatic ketones. High-cost catalysts and toxic solvents were generally needed in the present methodologies. Here, an efficient aqueous C?H aerobic oxidation protocol was reported. Through CeCl3-mediated photocatalysis, a series of aromatic ketones were produced in moderate to excellent yields. With air as the oxidant, this reaction could be performed under mild conditions in water and demonstrated high activity and functional group tolerance. This method is economical, highly efficient, and environmentally friendly, and it will provide inspiration for the development of aqueous photochemical synthesis reactions.

Metal- And additive-free C-H oxygenation of alkylarenes by visible-light photoredox catalysis

A metal- and additive-free methodology for the highly selective, photocatalyzed C-H oxygenation of alkylarenes under air to the corresponding carbonyls is presented. The process is catalyzed by an imide-acridinium that forms an extremely strong photooxidant upon visible light irradiation, which is able to activate inert alkylarenes such as toluene. Hence, this is an easy to perform, sustainable and environmentally friendly oxidation that provides valuable carbonyls from abundant, readily available compounds.

HCl-Catalyzed Aerobic Oxidation of Alkylarenes to Carbonyls

The construction of C?O bonds through C?H bond functionalization remains fundamentally challenging. Here, a practical chlorine radical-mediated aerobic oxidation of alkylarenes to carbonyls was developed. This protocol employed commercially available HCl as a hydrogen atom transfer (HAT) reagent and air as a sustainable oxidant. In addition, this process exhibited excellent functional group tolerance and a broad substrate scope without the requirement for external metal and oxidants. The mechanistic hypothesis was supported by radical trapping, 18O labeling, and control experiments.

The Origin of Catalytic Benzylic C?H Oxidation over a Redox-Active Metal–Organic Framework

Selective oxidation of benzylic C?H compounds to ketones is important for the production of a wide range of fine chemicals, and is often achieved using toxic or precious metal catalysts. Herein, we report the efficient oxidation of benzylic C?H groups in a broad range of substrates under mild conditions over a robust metal–organic framework material, MFM-170, incorporating redox-active [Cu2II(O2CR)4] paddlewheel nodes. A comprehensive investigation employing electron paramagnetic resonance (EPR) spectroscopy and synchrotron X-ray diffraction has identified the critical role of the paddlewheel moiety in activating the oxidant tBuOOH (tert-butyl hydroperoxide) via partial reduction to [CuIICuI(O2CR)4] species.