655-15-2

Usage

Uses

Used in Chemical Synthesis:
2-Bromo-2'-fluoroacetophenone is used as a key intermediate in the synthesis of various organic compounds, particularly those requiring specific halogenated aromatic structures. Its unique combination of bromine and fluorine atoms allows for versatile reactivity and functional group manipulation.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Bromo-2'-fluoroacetophenone is used as a building block for the development of new drugs with potential therapeutic applications. Its distinct structural features can contribute to the design of novel molecules with improved pharmacological properties.
Used in Catalyst Development:
2-Bromo-2'-fluoroacetophenone is utilized in the preparation of new classes of catalysts, such as acetophenone-based cinchona alkaloid-derived quaternary ammonium salts. These catalysts are evaluated for their performance in enantioselective alkylation of glycine imine esters, a crucial process in the synthesis of chiral compounds with potential applications in medicine and other fields.
Used in Material Science:
In material science, 2-Bromo-2'-fluoroacetophenone can be employed in the development of new materials with specific properties, such as improved thermal stability or enhanced chemical resistance. Its halogenated structure can influence the physical and chemical characteristics of the resulting materials.

InChI:InChI=1/C8H7FO2S/c1-12-5-2-3-7(9)6(4-5)8(10)11/h2-4H,1H3,(H,10,11)

Upstream product

• 445-27-2 2'-Fluoroacetophenone 
• 450-95-3 2-fluoroacetophenone 
• 1246224-44-1 1-(bromoethynyl)-2-fluorobenzene 

Downstream Products

• 143696-76-8 2-(2-Fluoro-phenyl)-imidazo[1,2-a]pyrimidine 
• 129486-34-6 4-(2-fluorophenyl)-2-<<4(5)-methyl-5(4)-imidazolyl>methyl>thiazole 
• 121041-72-3 2-(2-Fluoro-phenyl)-6-(2-methoxy-phenoxy)-imidazo[1,2-b]pyridazin-3-ol 
• 122479-50-9 2-(2-Fluoro-phenyl)-6-(3-methoxy-benzylamino)-imidazo[1,2-b]pyridazin-3-ol 
• 121041-80-3 2-(2-Fluoro-phenyl)-6-(3-methoxy-benzylsulfanyl)-imidazo[1,2-b]pyridazin-3-ol 
• 152801-51-9 2-fluorophenyl-brommethyl-O-methylketoxime 
• 310462-62-5 3-amino-1-ethoxycarbonyl-2-(2-fluorobenzoyl)indole 
• 310462-60-3 3-amino-2-(2-fluorobenzoyl)benzothiophene 
• 31915-26-1 3-(2-fluorophenyl)-3-oxo-propanenitrile 

Relevant academic research and scientific papers

Based on isoxazole substitution of benzamide derivatives and anti-prostate cancer drug applications

The present invention discloses a class (I), formula (II) structure based on isoxazole substituted benzamide derivatives and antiprostate cancer drug applications, such isoxazole substituted benzamide derivatives, can effectively inhibit the activity of a

Design and synthesis of 7-O-1,2,3-triazole hesperetin derivatives to relieve inflammation of acute liver injury in mice

Based on the previous research results of our research group, to further improve the anti-inflammatory activity of hesperetin, we substituted triazole at the 7-OH branch of hesperetin. We also evaluated the anti-inflammatory activity of 39 new hesperetin derivatives. All compounds showed inhibitory effects on nitric oxide (NO) and inflammatory factors in lipopolysaccharide-induced RAW264.7 cells. Compound d5 showed a strong inhibitory effect on NO (half maximal inhibitory concentration = 2.34 ± 0.7 μM) and tumor necrosis factor-α, interleukin (IL)-1β, and (IL-6). Structure–activity relationships indicate that 7-O-triazole is buried in a medium-sized hydrophobic cavity that binds to the receptor. Compound d5 can also reduce the reactive oxygen species production and significantly inhibit the expression of inducible NO synthase and cyclooxygenase-2 through the nuclear factor-κB signaling pathway. In vivo results indicate that d5 can reduce liver inflammation in mice with acute liver injury (ALI) induced by CCI4. In conclusion, d5 may be a candidate drug for treating inflammation associated with ALI.

High Chemo-/Stereoselectivity for Synthesis of Polysubstituted Monofluorinated Pyrimidyl Enol Ether Derivatives

A novel intramolecular Smiles rearrangement of α-fluoro-β-keto-pyrimidylsulfones (usually used as a carbon nucleophile) was developed, providing a versatile avenue for synthesis of tri/tetra-substituted monofluorinated pyrimidyl enol ethers. Among these, diverse (Z)-monofluorovinylsulfones and sulfinates were efficiently assembled by adding extra electrophile and fine-tuning reaction conditions. The process is triggered by a keto-enol tautomerism from enol oxyanion to pyrimidine 2-carbon, completely different from the classical carbon nucleophilic addition reaction approach.

Ru-Tethered (R,R)-TsDPEN with DMAB as an efficient catalytic system for high enantioselective one-pot synthesis of chiral β-aminolviaasymmetric transfer hydrogenation

This work reflects Ru-tethered-TsDPEN as an active chiral catalyst for one pot selective synthesis of optically active α-substituted alcohols and its derivatives from α-bromo ketones in the presence of dimethylamine borane (DMAB) as the hydrogen source. Various Ru-chiral catalysts have been screened and the methodology proceededviaa (R,R) Ru-tethered TsDPEN catalyst through asymmetric transfer hydrogenation (ATH) of the in-situ formed ketones to the corresponding chiral β-aminol product. Thus, the Ru-tethered TsDPEN-DMAB catalytic system works efficiently with higher yield and high enantiomeric excess over others for the ATH process. Based on a study ofortho,metaandparasubstituted α-bromo acetophenone derivatives, effective enantioselectivity has been observed fororthosubstituted β-aminol. The mechanism has been optimized depending on product analysis with the help of its kinetic AT-IR study. This work also focusses on the synthesis of various β-amino alcohol derivatives where the effect of an EWG and EDG on enantio-selectivity has been studied.

Base-Catalyzed Intramolecular Defluorination/O-Arylation Reaction for the Synthesis of 3-Fluoro-1,4-oxathiine 4,4-Dioxide

A novel process involving base-catalyzed intramolecular defluorination/O-arylation of readily available α-fluoro-β-one-sulfones was realized and provided a series of 3-fluoro-1,4-oxathiine 4,4-dioxide derivatives in good to excellent yields. Unlike traditional defluorination reactions with stoichiometric base as the deacid reagent, this process is triggered by a catalytic amount of base (TMG: tetramethylguanidine) and molecular sieves serve as both an adsorbent to remove HF acid and an activator to assist C-F bond cleavage.

Chiral Bidentate Phosphoramidite-Pd Catalyzed Asymmetric Decarboxylative Dipolar Cycloaddition for Multistereogenic Tetrahydrofurans with Cyclic N-Sulfonyl Ketimine Moieties

An asymmetric [3 + 2] cycloaddition of vinyl ethylenecarbonates (VECs) and (E)-3-arylvinyl substituted benzo[d] isothiazole 1,1-dioxides has been developed using the Pd complex of a bidentate phosphoramidite (Me-BIPAM) as the catalyst, providing a wide variety of chiral multistereogenic vinyltetrahydrofurans in good yields with excellent diastereo- and enantioselectivities (up to >20:1 dr, 99% ee).

Oxidation Potential-Guided Electrochemical Radical-Radical Cross-Coupling Approaches to 3-Sulfonylated Imidazopyridines and Indolizines

Oxidation potential-guided electrochemical radical-radical cross-coupling reactions between N-heteroarenes and sodium sulfinates have been established. Thus, simple cyclic voltammetry measurement of substrates predicts the likelihood of successful radical-radical coupling reactions, allowing the simple and direct synthetic access to 3-sulfonylated imidazopyridines and indolizines. The developed electrochemical radical-radical cross-coupling reactions to sulfonylated N-heteroarenes boast the green synthetic nature of the reactions that are oxidant- and metal-free.

Discovery of 5,6-Bis(4-methoxy-3-methylphenyl)pyridin-2-amine as a WSB1 Degrader to Inhibit Cancer Cell Metastasis

The gain of cell motility is an essential prerequisite for cancer metastasis. The ubiquitin ligase subunit WD repeat and SOCS box-containing 1 (WSB1) has been demonstrated to regulate hypoxia-driven tumor cell migration. However, there is still a lack of methods for discovering inhibitors targeting the WSB1 axis. Here, we employed phenotypic screening models and identified compound4that displayed migration inhibitory activity against WSB1-overexpressing cells. Further studies indicated that it may function as a WSB1 degrader, thus leading to the accumulation of the Rho guanosine diphosphate dissociation inhibitor 2 (RhoGDI2) protein, reversing the expression of downstream F-actin and formation of membrane ruffles, and disturbing the migration capacity of cancer cells. Moreover, compound4exhibited a promisingin vivoanticancer metastatic effects. Our findings show the discovery of a new WSB1 degrader, providing a unique solution for the treatment of cancer metastasis.

Synthesis method of 5-(2-fluorophenyl)-1H-pyrrole-3-formaldehyde

The invention discloses a synthetic method of 5-(2-fluorophenyl)-1H-pyrrole-3-formaldehyde, and belongs to the field of organic synthesis. The preparation method comprises the following steps: (1) reacting 2-fluoro acetophenone with a bromination reagent

Discovery of novel potent GPR40 agonists containing imidazo[1,2-a]pyridine core as antidiabetic agents

Free fatty acid receptor 1 (FFA1 or GPR40) has been studied for many years as a target for the treatment of type 2 diabetes mellitus. In order to increase potency and reduce hepatotoxicity, a series of novel compounds containing imidazo[1,2-a]pyridine sca