57486-67-6

Basic information

• Product Name: METHYL 2-FLUOROPHENYLACETATE
• Synonyms: METHYL 2-FLUOROPHENYLACETATE;2-FLUORO-PHENYLACETIC ACIDMETHYL ESTER;2-Flurophenylacetic acid methyl ester;Methyl 2-fluorophenylacetate,99%;Methyl 2-(2-fluorophenyl)acetate
• CAS NO: 57486-67-6
• Molecular Formula: C₉H₉FO₂
• Molecular Weight: 168.16
• Mol File: 57486-67-6.mol

Chemical Properties

• Boiling Point: 210°C (rough estimate)
• Flash Point: 76.8 °C
• Appearance: Clear colorless/Liquid
• Density: 1.1410 (estimate)
• Vapor Pressure: 0.235mmHg at 25°C
• Refractive Index: 1.489-1.491
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: METHYL 2-FLUOROPHENYLACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 2-FLUOROPHENYLACETATE(57486-67-6)
• EPA Substance Registry System: METHYL 2-FLUOROPHENYLACETATE(57486-67-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 57486-67-6(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
METHYL 2-FLUOROPHENYLACETATE is used as a reagent for catalytic enantioselective O-H insertion reactions, which are crucial in the synthesis of various complex organic molecules. Its application in this field is significant due to its ability to facilitate the formation of specific enantiomers, which are essential in the development of pharmaceuticals and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, METHYL 2-FLUOROPHENYLACETATE is used as a key intermediate in the synthesis of various drugs and drug candidates. Its role in enantioselective reactions allows for the production of chiral molecules with specific configurations, which are often necessary for the desired biological activity and efficacy of a drug.
Used in Research and Development:
METHYL 2-FLUOROPHENYLACETATE is also utilized in research and development laboratories for the exploration of new chemical reactions and the development of innovative synthetic methods. Its versatility as a reagent makes it a valuable tool for chemists working on the design and synthesis of novel compounds with potential applications in various industries.
Used in Material Science:
In the field of material science, METHYL 2-FLUOROPHENYLACETATE can be used as a building block for the development of new materials with specific properties. Its involvement in enantioselective reactions can lead to the creation of materials with unique structural features, which can be tailored for various applications, such as in the production of advanced polymers or coatings.

InChI:InChI=1/C9H9FO2/c1-12-9(11)6-7-4-2-3-5-8(7)10/h2-5H,6H2,1H3

Upstream product

• 67-56-1 methanol 
• 326-62-5 2-fluorophenyl acetonitrile 
• 451-82-1 (2-fluorophenyl)acetic acid 

Downstream Products

• 145983-09-1 methyl 2-(2-fluorophenyl)propanoate 
• 1011527-90-4 methyl 3-(3,5-dichloropyridin-2-yl)-2-(2-fluorophenyl)-3-oxopropanoate 
• 1011528-09-8 C₁₅H₁₁ClFNO₃ 
• 954125-24-7 1-tert-butyl 4-methyl 4-(2-fluorophenyl)piperidine-1,4-dicarboxylate 
• 50919-06-7 2-(2-fluorophenyl)ethanol 
• 1430086-83-1 C₁₇H₁₃ClFNO₃ 
• 1430088-19-9 C₁₆H₁₃FN₂O₃ 
• 1430086-75-1 C₁₇H₁₃F₂NO₃ 
• 116622-94-7 2-(2-fluorophenyl)acetohydrazide 
• 554436-95-2 4-amino-3-(2-fluorobenzyl)-1H-1,2,4-triazole-5(4H)-thione 
• 1427501-02-7 3-(2-fluorobenzyl)-6-(furan-3-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 36209-49-1 4-amino-5-(4-methoxyphenyl)-2,3-dihydro-4H-1,2,4-triazole-3-thione 
• 923550-56-5 3-(2-fluorobenzyl)-6-(pyridin-4-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 849913-13-9 3-(4-methoxyphenyl)-6-(pyridin-2-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 

Relevant articles and documents

Insertion of Diazo Esters into C-F Bonds toward Diastereoselective One-Carbon Elongation of Benzylic Fluorides: Unprecedented BF3Catalysis with C-F Bond Cleavage and Re-formation

Selective transformation of C-F bonds remains a significant goal in organic chemistry, but C-F insertion of a one-carbon-atom unit has never been established. Herein we report the BF3-catalyzed formal insertion of diazo esters as one-carbon-atom sources into C-F bonds to accomplish one-carbon elongation of benzylic fluorides. A DFT calculation study revealed that the BF3 catalyst could contribute to both C-F bond cleavage and re-formation. This elongation provided α-fluoro-α,β-diaryl esters with a high level of diastereoselectivity. Various benzylic fluorides and diazo esters were applicable. The synthetic utility of this method was demonstrated by the synthesis of a fluoro analogue of a compound that is used as a transient receptor and potential canonical channel inhibitor.

PYRAZOLOTRIAZOLOPYRIMIDINE DERIVATIVES AS A2A RECEPTOR ANTAGONIST

Disclosed herein is a pyrazolotriazolopyrimidine derivative or a stereoisomer thereof, or a pharmaceutically acceptable salt thereof useful as A2A receptor antagonist, and a pharmaceutical composition comprising the same. Also disclosed herein is a method of treating cancer using the pyrazolotriazolopyrimidine derivative or a stereoisomer thereof, or a pharmaceutically acceptable salt thereof as A2A receptor antagonist.

Pd-Catalyzed Decarboxylative Olefination: Stereoselective Synthesis of Polysubstituted Butadienes and Macrocyclic P-glycoprotein Inhibitors

The efficient and stereoselective synthesis of polysubstituted butadienes, especially the multifunctional butadienes, represents a great challenge in organic synthesis. Herein, we wish to report a distinctive Pd(0) carbene-initiated decarboxylative olefination approach that enables the direct coupling of diazo esters with vinylethylene carbonates (VECs), vinyl oxazolidinones, or vinyl benzoxazinones to afford alcohol-, amine-, or aniline-containing 1,3-dienes in moderate to high yields and with excellent stereoselectivity. This protocol features operational simplicity, mild reaction conditions, a broad substrate scope, and gram-scalability. Notably, a structurally unique allylic Pd(II) intermediate was isolated and characterized. DFT calculation and control experiments demonstrated that a rare Pd(0) carbene intermediate could be involved in this reaction. Moreover, the polysubstituted butadienes as novel building blocks were unprecedentedly assembled into macrocycles, which efficiently inhibited the P-glycoprotein and dramatically reversed multidrug resistance in cancer cells by 190-fold.

ARYL-SUBSTITUTED ACETAMIDE AND PYRROLIDIN-2-ONE DERIVATIVES AND THEIR USE FOR THE TREATMENT OF SEIZURES

Aryl-substituted acetamide and pyrrolidin-2-one (γ-butyrolactam) derivatives have useful activity in the inhibition, prevention, or treatment of seizures. The derivatives may be useful in the treatment of epilepsy, including medically refractory epilepsy, and nerve agent poisoning.

Synthesis and bio-evaluation of natural butenolides-acrylate conjugates

A series of novel 3-aryl-4-hydroxy-2(5H) furanone-acrylate hybrids were designed and synthesized based on the natural butenolides and acrylates scaffolds. The structures of the prepared compounds were characterized by 1H-NMR, 13C-NMR and electrospray ionization mass spectrometry (ESI-MS), and the bioactivity of the target compounds against twelve phytopathogenic fungi was investigated. The preliminary in vitro antifungal activity screening showed that most of the target compounds had moderate inhibition on various pathogenic fungi at the concentration of 100 mg·L?1, and presented broad-spectrum antifungal activities. Further studies also indicated that compounds 7e and 7k still showed some inhibitory activity against Pestallozzia theae, Sclerotinia sclerotiorum and Gibberella zeae on rape plants at lower concentrations, which could be optimized as a secondary lead for further research.

Dehydroxymethylation of alcohols enabled by cerium photocatalysis

Dehydroxymethylation, the direct conversion of alcohol feedstocks as alkyl synthons containing one less carbon atom, is an unconventional and underexplored strategy to exploit the ubiquity and robustness of alcohol materials. Under mild and redox-neutral reaction conditions, utilizing inexpensive cerium catalyst, the photocatalytic dehydroxymethylation platform has been furnished. Enabled by ligand-to-metal charge transfer catalysis, an alcohol functionality has been reliably transferred into nucleophilic radicals with the loss of one molecule of formaldehyde. Intriguingly, we found that the dehydroxymethylation process can be significantly promoted by the cerium catalyst, and the stabilization effect of the fragmented radicals also plays a significant role. This operationally simple protocol has enabled the direct utilization of primary alcohols as unconventional alkyl nucleophiles for radical-mediated 1,4-conjugate additions with Michael acceptors. A broad range of alcohols, from simple ethanol to complex nucleosides and steroids, have been successfully applied to this fragment coupling transformation. Furthermore, the modularity of this catalytic system has been demonstrated in diversified radical-mediated transformations including hydrogenation, amination, alkenylation, and oxidation.

Dehydroxymethylation of Alcohols Enabled by Cerium Photocatalysis

Dehydroxymethylation, the direct conversion of alcohol feedstocks as alkyl synthons containing one less carbon atom, is an unconventional and underexplored strategy to exploit the ubiquity and robustness of alcohol materials. Under mild and redox-neutral reaction conditions, utilizing inexpensive cerium catalyst, the photocatalytic dehydroxymethylation platform has been furnished. Enabled by ligand-to-metal charge transfer catalysis, an alcohol functionality has been reliably transferred into nucleophilic radicals with the loss of one molecule of formaldehyde. Intriguingly, we found that the dehydroxymethylation process can be significantly promoted by the cerium catalyst, and the stabilization effect of the fragmented radicals also plays a significant role. This operationally simple protocol has enabled the direct utilization of primary alcohols as unconventional alkyl nucleophiles for radical-mediated 1,4-conjugate additions with Michael acceptors. A broad range of alcohols, from simple ethanol to complex nucleosides and steroids, have been successfully applied to this fragment coupling transformation. Furthermore, the modularity of this catalytic system has been demonstrated in diversified radical-mediated transformations including hydrogenation, amination, alkenylation, and oxidation.

Palladium-Catalyzed Tandem Reaction of Three Aryl Iodides Involving Triple C-H Activation

A novel palladium-catalyzed tandem reaction of N-(2-iodoaryl)acrylamides with two aryl iodides for the synthesis of spirooxindole has been achieved. The reaction underwent the process of triple C-H activation and four C-C bond formations based on the double trapping of transient spirocyclic palladacycles which are obtained through remote C-H activation.

Stereoselective synthesis of 3,4-di-substituted mercaptolactones via photoredox-catalyzed radical addition of thiophenols

A visible light mediated radical addition of thiophenols on 4-phenylbut-3-enoic acids to give diastereoselective synthesis of 3,4-disubstituted γ-lactones is reported. The reaction precludes the conventional prerequisite of conjugate addition. Furthermore, the lactones were successfully utilized in the synthesis of γ-ketoamides.

HETEROCYCLIC COMPOUNDS

The present invention relates to compounds of the general formula (1) wherein the variables are defined as given in the description and claims. The invention further relates to uses of and to, processes and intermediates related to compounds of the general formula (I), wherein Q is wherein the substituents of I, Ia and Ib are as defined in description and claims.