405-51-6

Usage

Chemical Properties

Clear colourless liquid

InChI:InChI=1/C8H7FO2/c1-6(10)11-8-4-2-7(9)3-5-8/h2-5H,1H3

Upstream product

• 371-41-5 4-Fluorophenol 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 
• 830-03-5 4-nitrophenol acetate 
• 4232-27-3 2,4-dinitrophenyl acetate 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 459-60-9 1-fluoro-4-methoxybenzene 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 10534-59-5 tetrabutylammonium acetate 
• 201230-82-2 carbon monoxide 
• 74-88-4 methyl iodide 
• 456-22-4 4-Fluorobenzoic acid 
• 64-19-7 acetic acid 
• 24228-71-5 (4-fluorophenyl)(triphenylphosphine)gold(I) 

Downstream Products

• 364-32-9 4-fluoro-2,6-dinitrophenol 
• 123871-59-0 4-fluoro-4-nitrocyclohexa-2,5-dienone 
• 371-41-5 4-Fluorophenol 
• 1119-49-9 N-butylacetamide 
• 394-32-1 1-(5-fluoro-2-hydroxyphenyl)ethan-1-one 
• 618-42-8 1-piperidin-1-yl-ethanone 
• 32376-34-4 4-fluorophenolate anion 
• 2466-76-4 N-Acetylimidazole 
• 142-26-7 2-acetylaminoethanol 
• 543-24-8 N-acetylglycine 
• 569343-13-1 1-(4-fluorophenoxy)-1-(trimethylsiloxy)ethene 
• 622-45-7 cyclohexyl acetate 
• 596826-81-2 trans-1-acetoxy-4-fluorocyclohexane 
• 596826-81-2 cis-1-acetoxy-4-fluorocyclohexane 

Relevant academic research and scientific papers

Synthesis of fluorinated cycloalkyl N-phenylcarbamates and their microbial defluorination/oxygenation by Beauveria bassiana

Earlier investigations showed that cycloalkyl N-phenylcarbamates were hydroxylated by the fungus Beauveria bassiana predominantly in the 4-position relative to the electron-rich substituent. In cases involving fluorinated methylene groups potentially capable of hydroxylation, however, defluorination and formation of a ketone was observed. The formation of the ketone can be explained by primary hydroxylation to forman unstable geminal fluorohydrin, which is subsequently dehydrofluorinated. Wiley-VCH Verlag GmbH & Co. KGaAA, 69451 Weinheim, Germany, 2003.

Decarboxylative Hydroxylation of Benzoic Acids

Herein, we report the first decarboxylative hydroxylation to synthesize phenols from benzoic acids at 35 °C via photoinduced ligand-to-metal charge transfer (LMCT)-enabled radical decarboxylative carbometalation. The aromatic decarboxylative hydroxylation is synthetically promising due to its mild conditions, broad substrate scope, and late-stage applications.

An efficient method to prepare aryl acetates by the carbonylation of aryl methyl ethers or phenols

Synthesis of valuable chemicals from lignin based compounds is critical for the application of biomass. Here, we develop a method of preparing aryl acetates by the carbonylation of aryl methyl ethers or phenols under low CO pressure. Good to excellent yields of aryl acetates were obtained using different substrates, and a possible reaction mechanism was proposed by conducting a series of control experiments. This method may provide a potential way for the utilization of lignin.

Chromone dioxadiazole compound as well as preparation method and application thereof

The preparation method comprises the following steps: adding an intermediate F and bis (acetoxy) iodobenzene to dichloromethane for reaction to obtain the chromone compound. The invention provides a novel chromone dioxadiazole compound and a preparation method thereof, and overcomes the defects of large toxicity and high preparation cost of the traditional method.

Synthesis of novel of 2, 5-disubstituted 1, 3, 4- oxadiazole derivatives and their in vitro anti-inflammatory, anti-oxidant evaluation, and molecular docking study

A series of novel 2, 5-disubstituted 1, 3, 4-Oxadiazole derivatives as a potential anti-inflammatory, and anti-oxidant agent were synthesized via cyclisation. Hydrazide molecule treated with substituted acids in the presence of phosphorus oxychloride (POCl3) as an efficient reagent as well as solvent by conventional method with shorter reaction time and excellent yield. The newly synthesized 1, 3, 4- oxadiazole derivatives exhibited excellent to good anti-inflammatory and anti-oxidant activities compaired to the standard drugs. Molecular docking study on the crucial anti-inflammatory target–cyclooxygenase-2 (COX-2) revealed the ability of the scaffold to correctly recognize the active site and achieve significant bonded and non-bonded interactions with key residues therein. This study could identify potential compounds which can be pertinent starting points for structure-based drug design to obtain newer anti-inflammatory agents.

Novel p-functionalized chromen-4-on-3-yl chalcones bearing astonishing boronic acid moiety as MDM2 inhibitor: Synthesis, cytotoxic evaluation and simulation studies

Background: Novel 4-[3-(6/7/8-Substituted 4-Oxo-4H-chromen-3-yl)acryloyl]phenyl-boronic acid derivatives (5a-h) as well as other 6/7/8-substituted-3-(3-oxo-3-(4-substituted-phenyl)prop-1-enyl)-4H-chromen-4-one derivatives (3a-u) have been designed as p53-MDM2 pathway inhibitors and reported to possess significant cytotoxic properties against several cancer cell lines. Objectives: The current project aims to frame the structure-anticancer activity relationship of chromen-4-on-3-yl chalcones (3a-u/5a-h). In addition, docking studies were performed on these chromeno-chalcones in order to have an insight into their interaction possibilities with MDM2 pro-tein. Methods: Twenty-nine chromen-4-on-3-yl chalcone derivatives (3a-u/5a-h) were prepared by utilizing silica supported-HClO4 (green route with magnificent yield) and tested against four cancer cell lines (HCT116, MCF-7, THP-1, NCIH322). Results: Among the series 3a-u, compound 3b exhibited the highest anticancer activity (with IC50 values ranging from 8.6 to 28.4 μM) overall against tested cancer cell lines. Interestingly, para-Boronic acid derivative (5b) showed selective inhibition against colon cancer cell line, HCT-116 with an IC50 value of 2.35 μM. Besides the emblematic hydrophobic interactions of MDM2 inhibi-tors, derivative 5b was found to exhibit extra hydrogen bonding with GLN59 and GLN72 residues of MDM2 in molecular dynamics (MD) simulation. All the compounds were virtually nontoxic against normal fibroblast cells. Conclusion: Novel compounds were obtained with good anticancer activity especially 6-Chlorochromen-4-one substituted boronic acid derivative 5b. The molecular docking study proposed good activity as a MDM-2 inhibitor suggesting hydrophobic as well as hydrogen bonding interactions with MDM2.

Mechanistic Insights into C(sp2)?C(sp)N Reductive Elimination from Gold(III) Cyanide Complexes

A new family of phosphine-ligated dicyanoarylgold(III) complexes has been prepared and their reactivity towards reductive elimination has been studied in detail. Both, a highly positive entropy of activation and a primary 12/13C KIE suggest a late concerted transition state while Hammett analysis and DFT calculations indicate that the process is asynchronous. As a result, a distinct mechanism involving an asynchronous concerted reductive elimination for the overall C(sp2)?C(sp)N bond forming reaction is characterized herein, for the first time, complementing previous studies reported for C(sp3)?C(sp3), C(sp2)?C(sp2), and C(sp3)?C(sp2) bond formation processes taking place on gold(III) species.

Preparation method for synthesis of phenolic ester through thiocarboxylic acid mediated visible light catalyzed phenol acylation reaction

The invention discloses a preparation method for synthesis of phenolic ester through a thiocarboxylic acid mediated visible light catalyzed phenol acylation reaction. Thiocarboxylic acid compounds andphenol compounds are subjected to a site specific reaction under certain conditions to produce phenolic ester compounds, wherein the certain conditions are as follows: under the conditions of normaltemperature, normal pressure and visible light, K2CO3 is used as an alkaline catalyst, terpyridyl ruthenium dichloride hexahydrate is used as a photosensitizer and acetonitrile is used as a reaction solvent. Synthesis of phenolic ester under catalysis of visible light is realized, thiocarboxylic acid is used as an acylation reagent, and the site specific phenol esterification reaction is realizedefficiently under mild conditions of normal temperature, normal pressure and visible light. The method has mild reaction conditions, large substrate functional group tolerance, high applicability andhigh yield, and an efficient, reliable and economical preparation method is provided for synthesis of phenolic ester.

Synthesis and characterization of new N-alkylated pyridin-2(1H)-ones

A series of novel N-substituted pyridin-2(1H)-one derivatives have been synthesized by reacting (E)-ethyl 3-(6-fluoro-4-oxo-4H-chromen-3-yl)acrylate, with various alkylamines, benzylamines, diaminoalkanes, propargyl amine, 2-amino-1,3-dihydroxypropane, etc. under basic conditions, in 60-83% yield. The structures of the compounds have been established on the basis of their physical and spectral characterization data (1H and 13C NMR, UV-Vis, FT-IR, and HRMS) and further confirmed by X-ray crystallographic analysis of a representative compound. Antibacterial activity of obtained 2-pyridones have been investigated against three human pathogen bacterial strains. Most of the compounds exhibit low activity as compared to the reference.

Copper-Mediated Functionalization of Aryl Trifluoroborates

This paper describes the Cu(OTf)2-mediated coupling of aryl and heteroaryl trifluoroborates with tetrabutylammonium or alkali metal salts to form C-O, C-N, and C-halogen bonds. The reactions proceed under mild conditions (often room temperature over 16 hours) with carboxylate, halide, and azide salts, all nucleophiles that have been underrepresented in the copper cross-coupling literature. Preliminary results show that copper salts bearing weakly coordinating X-type ligands are essential for enabling these transformations to proceed under mild conditions.