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

• 403-43-0 4-fluorobenzoyl chloride 
• 462-06-6 fluorobenzene 
• 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 
• 73585-52-1 1-(1,1-dimethoxyethyl)-4-fluorobenzene 
• 52-86-8 haloperidol 
• 98516-45-1 (4-acetyl-phenyl)-dimethyl sulfonium ; methyl sulfate 
• 766-98-3 1-ethynyl-4-fluorobenzene 
• 64-19-7 acetic acid 
• 98-86-2 acetophenone 

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%.

Hydration of Alkynes to Ketones with an Efficient and Practical Polyoxomolybdate-based Cobalt Catalyst

Hydration of alkynes to ketones is one of the most atom economical and universal methods for the synthesis of carbonyl compounds. However, the basic reaction usually requires organic ligand catalysts or harsh reaction conditions to insert oxygen into the C≡C bond. Here, we report an inorganic ligand supported cobalt (III) catalyst, (NH4)3[CoMo6O18(OH)6], which is supported by a central cobalt (III) mononucleus and a ring-shaped pure inorganic ligand composed of six MoVIO6 octahedrons to avoid the disadvantages of expensive and unrecyclable organic ligand catalysts or noble metal catalysts. Under mild conditions, the cobalt (III) catalyst can be used for the hydration of alkynes to ketones. The catalyst is non-toxic, green, and environment friendly. The catalyst can be recycled at least six times with high activity. According to control experiments, a reasonable mechanism is provided.

Catalyst- and acid-free Markovnikov hydration of alkynes in a sustainable H2O/ethyl lactate system

An efficient and sustainable protocol for the hydration of alkynes has been developed under metal/acid/catalyst/ligand-free conditions in a water/ethyl lactate mixture. The hydrogen-bond network in the ethyl lactate and water mixture plays a crucial and decisive role in activating the alkynes for hydration to afford the corresponding methyl ketones. This strategy gives the Markovnikov (ketone) addition product selectively over other possible products. The essential role of hydrogen bonding has been confirmed by experimental and theoretical techniques. A probable mechanism has been suggested by various control tests. The efficacy of the method has been further explored for the competent production of value-added α,β-unsaturated carbonyl compounds through the reaction of aldehydes with alkynes as ketonic surrogates. The environmentally benign hydration method takes place under mild conditions, has broad functional-group compatibility, and uses the ethyl lactate/water (1:3) medium as a “green alternative” in the absence of any hazardous, harmful, or expensive substances.

Surface Coordination of Multiple Ligands Endows N-Heterocyclic Carbene-Stabilized Gold Nanoclusters with High Robustness and Surface Reactivity

Deciphering the molecular pictures of the multi-component and non-periodic organic-inorganic interlayer is a grand technical challenge. Here we show that the atomic arrangement of hybrid surface ligands on metal nanoparticles can be precisely quantified through comprehensive characterization of a novel gold cluster, Au44(iPr2-bimy)9(PA)6Br8 (1), which features three types of ligands, namely, carbene (1,3-diisopropylbenzimidazolin-2-ylidene, iPr2-bimy), alkynyl (phenylacetylide, PA), and halide (Br), respectively. The delicately balanced stereochemical effects and bonding capabilities of the three ligands give rise to peculiar geometrical and electronic structures. Remarkably, despite its complex and highly distorted surface structure, cluster 1 exhibits unusual catalytic properties and yet it is highly stable, both chemically and thermally. Moreover, rich reactive sites on the cluster surface raise the prospect of bio-compatibility (as it can be functionalized to yield water-soluble derivatives) and bio-applications.

One-Pot Chemoenzymatic Conversion of Alkynes to Chiral Amines

A one-pot chemoenzymatic sequential cascade for the synthesis of chiral amines from alkynes was developed. In this integrated approach, just ppm amounts of gold catalysts enabled the conversion of alkynes to ketones (>99%) after which a transaminase was used to catalyze the production of biologically valuable chiral amines in a good yield (up to 99%) and enantiomeric excess (>99%). A preparative scale synthesis of (S)-methylbenzylamine and (S)-4-methoxy-methylbenzylamine from its alkyne form gave a yield of 59 and 92%, respectively, withee> 99%.

Oxidative Cleavage of Alkenes by O2with a Non-Heme Manganese Catalyst

The oxidative cleavage of C═C double bonds with molecular oxygen to produce carbonyl compounds is an important transformation in chemical and pharmaceutical synthesis. In nature, enzymes containing the first-row transition metals, particularly heme and non-heme iron-dependent enzymes, readily activate O2 and oxidatively cleave C═C bonds with exquisite precision under ambient conditions. The reaction remains challenging for synthetic chemists, however. There are only a small number of known synthetic metal catalysts that allow for the oxidative cleavage of alkenes at an atmospheric pressure of O2, with very few known to catalyze the cleavage of nonactivated alkenes. In this work, we describe a light-driven, Mn-catalyzed protocol for the selective oxidation of alkenes to carbonyls under 1 atm of O2. For the first time, aromatic as well as various nonactivated aliphatic alkenes could be oxidized to afford ketones and aldehydes under clean, mild conditions with a first row, biorelevant metal catalyst. Moreover, the protocol shows a very good functional group tolerance. Mechanistic investigation suggests that Mn-oxo species, including an asymmetric, mixed-valent bis(μ-oxo)-Mn(III,IV) complex, are involved in the oxidation, and the solvent methanol participates in O2 activation that leads to the formation of the oxo species.