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Usage

Uses

Used in Pharmaceutical Industry:
2',4'-Difluoroacetophenone is used as a starting reagent for the synthesis of difluorinated chalcones, which are important intermediates in the development of various pharmaceutical compounds. These chalcones have potential applications in the treatment of different diseases due to their unique chemical properties and biological activities.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2',4'-Difluoroacetophenone serves as a valuable building block for creating a range of fluorinated organic compounds. The presence of fluorine atoms in its structure can significantly influence the reactivity, stability, and biological activity of the resulting molecules, making it a versatile starting material for various synthetic applications.

Upstream product

• 372-18-9 1,3-Difluorobenzene 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 
• 13918-92-8 2,4-difluorobenzene-1-sulfonyl chloride 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 51336-94-8 2-chloro-1-(2,4-dichlorophenyl)ethanone 
• 75-05-8 acetonitrile 
• 348-57-2 2,4-difluorobromobenzene 

Downstream Products

• 2267-47-2 1-(2,4-difluorophenyl)ethan-1-ol 
• 98556-24-2 2,2-dibromo-1-(2,4-difluoro-phenyl)-ethanone 
• 150555-91-2 4-fluoro-2-(phenylmethylthio)benzaldehyde 
• 150555-92-3 1-(2-(benzylthio)-4-fluorophenyl)ethan-1-one 
• 142472-18-2 1,3-di-(2,4-difluorophenyl)-1,3-propanedione 
• 79784-36-4 2-(2,4-difluorophenyl)-2-oxoacetaldehyde 
• 179011-35-9 2,4-difluoro-5-nitroacetophenone 
• 64287-17-8 1-(2,4-Difluoro-phenyl)-butane-1,3-dione 
• 102429-07-2 2-bromo-2',4'-difluoroacetophenone 
• 219488-04-7 RL₃₉₉ 
• 175846-98-7 N-<1-(2,4-difluorophenyl)ethylidene>-2-(trifluoromethyl)aniline 
• 220996-60-1 2-(2,2,2-trifluoroethoxy)-4-fluoroacetophenone 
• 1583-58-0 2,4-difluoro-benzoic acid 
• 405196-57-8 4-(2,4-difluoro-phenyl)-4-oxo-butyric acid tert-butyl ester 

Relevant academic research and scientific papers

Promoting charge separation in donor-acceptor conjugated microporous polymers: Via cyanation for the photocatalytic reductive dehalogenation of chlorides

Conjugated microporous polymers (CMPs) have emerged as promising heterogeneous photocatalysts for organic transformations owing to their structural designability and functional versatility. However, limited by the insufficient separation of the photo-generated excitons, their photocatalytic efficiency falls far short of expectations. Herein, we demonstrate a cyanation strategy to promote charge carrier separation in CMPs by selectively incorporating carbazole and cyano groups as electron-donating and electron-withdrawing units, respectively. The resulting CMPs feature π-extended donor (D)-acceptor (A) conjugation structures endowing them with distinct semiconducting properties, in which the efficient charge separation and transfer and wide visible-light absorption are facilitated. Compared to the cyano-free counterpart, the cyano-functionalized CMPs showed superior photocatalytic efficiency as exemplified by photocatalytic reductive dehalogenation of chlorides. More prominently, full recyclability of the designed CMPs as well as catalytic activity for at least ten runs without the loss of catalytic performance in photocatalytic reductive dehalogenation of chlorides demonstrated their robustness and sustainability. This journal is

Pd-Catalysed direct C(sp2)-H fluorination of aromatic ketones: Concise access to anacetrapib

The Pd-cataylsed direct ortho-C(sp2)-H fluorination of aromatic ketones has been developed for the first time. The reaction features good regioselectivity and simple operations, constituting an alternative shortcut to access fluorinated ketones. A concise synthesis of anacetrapib has also been achieved by using late-stage C-H fluorination as a key step.

Synthesis of 2-fluorocholine aryl carbonyl compounds

The invention provides a method for synthesizing 2-fluoroarylcarbonyl compounds, which comprises the following steps: converting arylcarbonyl compounds into corresponding carbonyl oxime ether compounds, mildly implementing aryl hydrocarbon chain direct fluoridation of high-selectivity oximido substituent group ortho-position in the presence of a palladium catalyst, a fluoridation reagent and additives, and finally, rehydrolyzing oxime ethers under the action of acid to obtain the 2-fluoroarylcarbonyl compounds. The fluoridation method has the advantages of mild reaction conditions, high substrate adaptability, high fluoridation selectivity and the like, is simple to operate, and has higher application research value.

Palladium(II)-catalyzed desulfitative synthesis of aryl ketones from sodium arylsulfinates and nitriles: Scope, limitations, and mechanistic studies

A fast and efficient protocol for the palladium(II)-catalyzed production of aryl ketones from sodium arylsulfinates and various organic nitriles under controlled microwave irradiation has been developed. The wide scope of the reaction has been demonstrated by combining 14 sodium arylsulfinates and 21 nitriles to give 55 examples of aryl ketones. One additional example illustrated that, through the choice of the nitrile reactant, benzofurans are also accessible. The reaction mechanism was investigated by electrospray ionization mass spectrometry and DFT calculations. The desulfitative synthesis of aryl ketones from nitriles was also compared to the corresponding transformation starting from benzoic acids. Comparison of the energy profiles indicates that the free energy requirement for decarboxylation of 2,6-dimethoxybenzoic acid and especially benzoic acid is higher than the corresponding desulfitative process for generating the key aryl palladium intermediate. The palladium(II) intermediates detected by ESI-MS and the DFT calculations provide a detailed understanding of the catalytic cycle. (Figure Presented).

SAR, cardiac myocytes protection activity and 3D-QSAR studies of salubrinal and its potent derivatives

Salubrinal is a selective inhibitor of endoplasmic reticulum (ER) stress and affords remarkable protection to cardiomyocytes. By studying the structure-activity relationship (SAR) of salubrinal, it was found that modification of the quinoline ring terminus and thiourea unit could confer the compound PP1-24 with markedly enhanced cardioprotective activity (EC 50 2 = 0.741, r2 = 0.991).

Synthesis of functionalised acetophenone

Nickel catalysed Heck arylation of the electron-rich olefin n-butyl vinyl ether with a wide variety of aryl bromides has been accomplished in the ionic liquid [bmim][BF4], affording an efficient green chemistry synthetic procedure for preparing functionalised acetophenone. The reaction gave a high regioselectivity and high yield without the need for the costely or toxic halide scavengers, leading predominantly to a branch-arylated α-product.

Fragmentation of radical anions of polyfluorinated benzoates

A comprehensive study of the symmetry forbidden fragmentation of short-lived radical anions (RAs) has been undertaken for the complete set of polyfluorinated benzoates (C6FnH5-nCO22, n = 1-5). The decay rate constants (kc) of RAs have been determined in aqueous alkaline solution (pH 13.4) by electron photoinjection (EPI) from mercury electrodes and were found to increase dramatically from ≤3 × 103 s-1 (3-F - C6H4CO2-) to (1.2 ± 0.8) × 109 s-1 (C6F5CO2-). The regioselectivity of C-F bond cleavage in the RA fragmentation has been revealed by structure assignment of reduction products of the polyfluorinated benzoic acids by Na, K, and Zn in liquid NH3, as well as by Zn in aqueous NH3 and aqueous alkaline solutions. The kc values depend on the position of the cleaved fluorine to the CO2- group generally in the order para > ortho > meta, and to sharply increase if adjacent fluorine atoms are present. The observed trends reveal that the kinetics of the RA fragmentation reaction is not controlled by the reaction thermodynamics. Semiempirical UHF/INDO calculations, the validity of which has been confirmed by ab initio ROHF/6-31+G calculations, were done to rationalize the observed trends. The reaction transition state (TS) was considered to arise from the RA's and 2*states crossing avoided due to out-of-plane deviation of the cleaving C-F bond. The satisfactory linear correlation (R = 0.96) between the model reaction energy barrier Ea and log kc has been achieved with modeling the local solvation of the CO2- group by its protonation.

FLUORINE CONTAINING BIOACTIVE HETEROCYCLES PART III : SYNTHESIS OF SOME NEW FLUORINE CONTAINING PHENYLGLYOXALS AND 1,2,4-TRIAZINE DERIVATIVES

Some medicinally important new fluorine containing phenylglyoxals have been synthesized by selenium dioxide oxidation of appropriate fluorinated acetophenones and characterized by spectrum studies.The phenylglyoxals were treated with thiosemicarbazide to give corresponding thiosemicarbazones (III) which were cyclized, in situ, to yield 5-(fluorophenyl)-1,2,4-triazine-3(2H)-thiones.The 5-(4-fluorophenyl)-1,2,4-triazine-3-(2H)-thione (IV) undergoes nucleophilic displacement when refluxed with hydrazine hydrate to give corresponding 3-hydrazino-5-(4-fluorophenyl)-1,2,4-tria zine.The hydrazino derivative reacts with fluorinated 1,3-diketones, in glacial acetic acid yielding 5-(4-fluorophenyl)-3--1,2,4-triazines (VII).All synthesized compounds have been characterized on the basis of elemental analyses, ir, pmr and 19F nmr studies.