247179-37-9

Basic information

• Product Name: 1-(4-Fluorophenyl)-2-Methoxyethanone
• Synonyms: 1-(4-Fluorophenyl)-2-Methoxyethanone
• CAS NO: 247179-37-9
• Molecular Formula: C₉H₉FO₂
• Molecular Weight: 168.1649632
• Mol File: 247179-37-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(4-Fluorophenyl)-2-Methoxyethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-Fluorophenyl)-2-Methoxyethanone(247179-37-9)
• EPA Substance Registry System: 1-(4-Fluorophenyl)-2-Methoxyethanone(247179-37-9)

Safety Data

• Hazardous Substances Data: 247179-37-9(Hazardous Substances Data)

Usage

Type of compound

Aromatic ketone

Structural features

4-fluorophenyl group
Methoxyethyl moiety

Applications

Reagent in organic synthesis
Pharmaceutical research
Development of new drugs (due to various biological activities)
Preparation of other organic compounds
Flavor and fragrance ingredient

Industry applications

Wide range of industries, including pharmaceutical, chemical, and flavor & fragrance industries.

Upstream product

• 67-56-1 methanol 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 1194-02-1 4-fluorobenzonitrile 
• 4009-98-7 (methoxymethyl)triphenylphosphonium chloride 
• 1738-36-9 2-methoxyacetonitrile 
• 352-13-6 4-flourophenylmagnesium bromide 
• 124-41-4 sodium methylate 
• 456-04-2 2-Chloro-4'-fluoroacetophenone 
• 403-29-2 2-bromo-4'-fluoroacetophenone 
• 1280738-13-7 ((1-(4-fluorophenyl)vinyl)oxy)triisopropylsilane 
• 460-00-4 1-Bromo-4-fluorobenzene 

Downstream Products

• 4640-67-9 3-(4-fluorophenyl)-3-oxopropionitrile 
• 132812-72-7 4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocyclooctane[b]pyridine-(1H)-ketone 
• 654674-10-9 (α-methoxy-4-fluorobenzyl)-(4-fluorophenyl)-ketone 

Relevant articles and documents

Intermolecular C-O Bond Formation with Alkoxyl Radicals: Photoredox-Catalyzed α-Alkoxylation of Carbonyl Compounds

Due to the high reactivity of alkoxyl (RO·) radicals and their propensity to easily undergo β-scission or Hydrogen Atom Transfer (HAT) reactions, intermolecular alkoxylations involving RO· radicals are barely described. We report herein for the first time the efficient intermolecular trapping of alkoxyl radicals by silyl enol ethers. This photoredox-mediated protocol enables the introduction of both structurally simple and more complex alkoxy groups into a wide range of ketones and amides.

NOVEL THYROMIMETICS

Compounds are provided having the structure of Formula (I): or a pharmaceutically acceptable isomer, racemate, hydrate, solvate, isotope, or salt thereof, wherein A, X1, X2, Q, R1, R2 and n are as defined herein. Such compounds function as thyromimetics and have utility for treating diseases such as neurodegenerative disorders and fibrotic diseases. Pharmaceutical compositions containing such compounds are also provided, as are methods of their use and preparation.

Tandem Acid/Pd-Catalyzed Reductive Rearrangement of Glycol Derivatives

Herein, we describe the acid/Pd-tandem-catalyzed transformation of glycol derivatives into terminal formic esters. Mechanistic investigations show that the substrate undergoes rearrangement to an aldehyde under [1,2] hydrogen migration and cleavage of an oxygen-based leaving group. The leaving group is trapped as its formic ester, and the aldehyde is reduced and subsequently esterified to a formate. Whereas the rearrangement to the aldehyde is catalyzed by sulfonic acids, the reduction step requires a unique catalyst system comprising a PdII or Pd0 precursor in loadings as low as 0.75 mol % and α,α′-bis(di-tert-butylphosphino)-o-xylene as ligand. The reduction step makes use of formic acid as an easy-to-handle transfer reductant. The substrate scope of the transformation encompasses both aromatic and aliphatic substrates and a variety of leaving groups.

METALLOENZYME INHIBITOR COMPOUNDS

Provided are compounds having HDAC6 modulating activity, and methods of treating diseases, disorders or symptoms thereof mediated by HDAC6.

Direct Synthesis of α-Alkoxy Ketones by Oxidative C–O Bond Formation

A convenient method to prepare α-alkoxy ketones has been developed by oxidative coupling of aryl methyl ketones and alcohols. With aqueous tert-butyl hydroperoxide (6.0 equiv.) as the oxidant, tetrabutylammonium iodide (20 mol-%) as the catalyst, and TsNHNH2(1.0 equiv.) as the additive, ketones underwent direct alkoxylation to give α-methoxy or α-ethoxy ketones in moderate to good yields.

Experimental study on the reaction pathway of α-haloacetophenones with NaOMe: Examination of bifurcation mechanism

The reaction of PhCOCH2Br and NaOMe in MeOH gave PhCOCH 2OH as the major product and PhCOCH2OMe as the minor product. Substituent effects on the reactivity and product selectivity revealed that an electron-withdrawing substituent on the phenyl ring enhanced the overall reactivity and gave more alcohol than ether. It was indicated that the alcohol was formed via carbonyl addition-epoxidation, whereas the ether was formed by direct substitution. Substituent effects on the reaction rates, as well as the effects of NaOMe concentration on the rate and product ratio for both reactions of PhCOCH2Br and PhCOCH2CI are in line with the mechanism that the alcohol and ether products were formed via two independent and concurrent routes, carbonyl addition and a-carbon attack, respectively, and thus the reaction mechanism could be different from the bifurcation mechanism previously predicted for the reaction of PhCOCH2Br by a simulation study in the gas phase.

CHEMICAL COMPOUNDS

Compounds of formula (I):wherein variable groups are as defined within; for use in the inhibition of 11betaHSD1 are described

Reaction of phosphonium ylides and aromatic nitriles under lewis acid conditions: An easy access to aryl-substituted α-methoxyacetophenones

In the presence of lithium chloride, as Lewis acid, the reaction of methoxymethyltriphenylphosphonium ylide 1 with aromatic nitriles 2 as phenacyl cation equivalents gives access to the corresponding α- methoxyacetophenones 3 in good yields.