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

• 462-06-6 fluorobenzene 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 73585-52-1 1-(1,1-dimethoxyethyl)-4-fluorobenzene 
• 86452-55-3 1-(p-acetophenyl)-3,3-diethyl-1-triazene 
• 98-86-2 acetophenone 
• 87261-60-7 N-(4-acetylphenylazo)piperidine 
• 76-05-1 trifluoroacetic acid 
• 403-41-8 1-(4-Fluorophenyl)ethanol 
• 74087-85-7 3,3-dimethyldioxirane 
• 352-34-1 4-fluoro-1-iodobenzene 
• 350-40-3 2-(4-fluorophenyl)-1-propene 
• 456-04-2 2-Chloro-4'-fluoroacetophenone 
• 100-12-9 4-ethylnitrobenzene 

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 
• 56835-39-3 4-(4-fluoro-phenyl)-1,3,4-trimethyl-4,8-dihydro-1H-pyrazolo[3,4-e][1,4]thiazepin-7-one 
• 62496-86-0 2,4,6-tris-(4-fluoro-phenyl)-phosphinine 
• 10342-85-5 4-piperidinoacetophenone 
• 125160-88-5 6-hydroxy-1-(p-fluorophenyl)hexane-1,3-dione 
• 18060-45-2 2-(4-fluoro-phenyl)-8-methyl-quinoline-4-carboxylic acid 
• 91021-13-5 6-Fluoro-3-[2-(4-fluoro-phenyl)-2-oxo-ethyl]-3-hydroxy-1,3-dihydro-indol-2-one 
• 142161-53-3 4'-(4-methylimidazol-1-yl)acetophenone 
• 154374-24-0 3-<3-(4-fluorophenyl)-3-oxo-propene-1-yl>-2-phenyl-indole 
• 18060-39-4 2-(4-Fluorphenyl)-8-trifluormethyl-cinchoninsaeure 
• 73585-52-1 1-(1,1-dimethoxyethyl)-4-fluorobenzene 
• 34837-84-8 4-fluorobenzeneacetic acid methyl ester 

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%.

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.

Method for preparing carbonyl compound through oxidative cleavage of visible light excitation aqueous solution quantum dot catalytic olefin compound

The invention provides a method for preparing carbonyl compounds through oxidative cleavage of a visible light excitation aqueous solution quantum dot catalytic olefin compound. Belong to photocatalysis synthesis technical field. To the method, an aqueous solution quantum dot is used as a photocatalyst, and an aqueous solution quantum dot activated molecular oxygen catalytic oxidation aromatic alkene compound is excited by visible light to be cracked to prepare a carbonyl compound. Low-loading capacity is used, a simple aqueous solution quantum dot is used as a catalyst, the yield of the carbonyl compound is high, TON more than ten millions are obtained. The reaction conditions are mild, water serves as a main solvent for the reaction, and the carbonyl compound can be obtained by catalytic olefin compound oxidation cracking without addition of a cocatalyst or the like. The method is simple to operate, wide in substrate range and low in cost.

Selective oxidation of alkenes to carbonyls under mild conditions

Herein, a practical and sustainable method for the synthesis of aldehydes, ketones, and carboxylic acids from an inexpensive olefinic feedstock is described. This transformation features very sustainable and mild conditions and utilizes commercially available and inexpensive tetrahydrofuran as the additive, molecular oxygen as the sole oxidant and water as the solvent. A wide range of substituted alkenes were found to be compatible, providing the corresponding carbonyl compounds in moderate-to-good yields. The control experiments demonstrated that a radical mechanism is responsible for the oxidation reaction.

Decatungstate-mediated solar photooxidative cleavage of CC bonds using air as an oxidant in water

With the increasing attention for green chemistry and sustainable development, there has been much interest in searching for greener methods and sources in organic synthesis. However, toxic additives or solvents are inevitably involved in most organic transformations. Herein, we first report the combination of direct utilization of solar energy, air as the oxidant and water as the solvent for the selective cleavage of CC double bonds in aryl olefins. Various α-methyl styrenes, diaryl alkenes as well as terminal styrenes are well tolerated in this green and sustainable strategy and furnished the desired carbonyl products in satisfactory yields. Like heterogeneous catalysis, this homogeneous catalytic system could also be reused and it retains good activity even after repeating three times. Mechanism investigations indicated that both O2- and 1O2 were involved in the reaction. Based on these results, two possible mechanisms, including the electron transfer pathway and the energy transfer pathway, were proposed.

Visible-Light-Driven Oxidative Cleavage of Alkenes Using Water-Soluble CdSe Quantum Dots

The oxidative cleavage of C=C bonds is an important chemical reaction, which is a popular reaction in the photocatalytic field. However, high catalyst-loading and low turnover number (TON) are general shortcomings in reported visible-light-driven reactions. Herein, the direct oxidative cleavage of C=C bonds through water-soluble CdSe quantum dots (QDs) is described under visible-light irradiation at room temperature with high TON (up to 3.7×104). Under the same conditions, water-soluble CdSe QDs could also oxidize sulfides to sulfoxides with 51–84 % yields and TONs up to 3.4×104. The key features of this photocatalytic protocol include high TONs, wide substrates scope, low catalyst loadings, simple and mild reaction conditions, and molecular O2 as the oxidant.