457-45-4

Usage

Uses

Used in Pharmaceutical Synthesis:
2-Fluoro-3-phenylpropanoic acid is used as a key intermediate for the development of new pharmaceuticals, leveraging its unique reactivity and structural properties to enhance the efficacy and safety profiles of resulting drug candidates.
Used in Agrochemical Development:
In the agrochemical industry, 2-Fluoro-3-phenylpropanoic acid is utilized as a building block for the synthesis of various agrochemicals, contributing to the creation of effective and safer products for agricultural applications.
Used in Medicinal Chemistry Research:
2-Fluoro-3-phenylpropanoic acid serves as a valuable component in medicinal chemistry research, where its structure can be modified to explore new drug candidates with improved biological activity and chemical interactions, particularly due to the influence of the phenyl group present in the molecule.

Upstream product

• 20397-58-4 ethyl (E)-2-fluoro-3-phenylacrylate 
• 135912-77-5 (S)-2-methanesulfonyloxy-3-phenylpropionic acid methyl ester 
• 107365-23-1 2-fluoro-3-phenylpropanal 
• 350-90-3 (Z/E)-2-fluoro-3-phenylprop-2-enoic acid 
• 607-81-8 diethyl 2-benzylmalonate 
• 105198-14-9 1-bromo-2-fluoro-3-phenylpropane 
• 300-57-2 allylbenzene 
• 117751-44-7 ethyl α-fluoro-α-nitro-β-phenylpropionate 
• 146746-22-7 (S)-2-Methanesulfonyloxy-3-phenyl-propionic acid isopropyl ester 
• 175897-68-4 isopropyl 2-hydroxy-3-phenylpropanoate 
• 13674-16-3 methyl 2-hydroxy-3-phenylpropanoate 
• 136291-66-2 2-fluoro-3-phenyl propane-1-oate de methyle 
• 330-80-3 ethyl 2-fluoro-3-phenylpropanoate 
• 1578-79-6 diethyl 2-benzyl-2-fluoromalonate 

Downstream Products

• 412018-61-2 C₉H₈ClFO 
• 1273308-55-6 2-(4-chlorophenyl)-4-(2-fluoro-3-phenylpropanoylamino)thiophene-3-carboxylic acid 
• 1273308-64-7 C₂₉H₂₃ClFNO₅S 
• 1273308-67-0 C₂₁H₁₇ClFNO₃S 
• 151588-82-8 (2-fluoro-2-iodoethyl)benzene 
• 151588-78-2 (2-bromo-2-fluoroethyl)benzene 
• 1616366-03-0 (2-fluoro-5-phenylpentyl)benzene 
• 151588-74-8 (2-fluoro-2-chloroethyl)benzene 
• 1616366-34-7 2-(4-fluoro-5-phenylpentyl)anisole 
• 146805-76-7 (R)-2-fluoro-3-phenylpropionic acid 
• 297183-00-7 (S)-2-fluoro-3-phenylpropionic acid 
• 828-01-3 D-phenyllactic acid 

Relevant academic research and scientific papers

Cobalt-Catalyzed Asymmetric Hydrogenation of α,β-Unsaturated Carboxylic Acids by Homolytic H2 Cleavage

The asymmetric hydrogenation of α,β-unsaturated carboxylic acids using readily prepared bis(phosphine) cobalt(0) 1,5-cyclooctadiene precatalysts is described. Di-, tri-, and tetra-substituted acrylic acid derivatives with various substitution patterns as well as dehydro-α-amino acid derivatives were hydrogenated with high yields and enantioselectivities, affording chiral carboxylic acids including Naproxen, (S)-Flurbiprofen, and a d-DOPA precursor. Turnover numbers of up to 200 were routinely obtained. Compatibility with common organic functional groups was observed with the reduced cobalt(0) precatalysts, and protic solvents such as methanol and isopropanol were identified as optimal. A series of bis(phosphine) cobalt(II) bis(pivalate) complexes, which bear structural similarity to state-of-the-art ruthenium(II) catalysts, were synthesized, characterized, and proved catalytically competent. X-band EPR experiments revealed bis(phosphine)cobalt(II) bis(carboxylate)s were generated in catalytic reactions and were identified as catalyst resting states. Isolation and characterization of a cobalt(II)-substrate complex from a stoichiometric reaction suggests that alkene insertion into the cobalt hydride occurred in the presence of free carboxylic acid, producing the same alkane enantiomer as that from the catalytic reaction. Deuterium labeling studies established homolytic H2 (or D2) activation by Co(0) and cis addition of H2 (or D2) across alkene double bonds, reminiscent of rhodium(I) catalysts but distinct from ruthenium(II) and nickel(II) carboxylates that operate by heterolytic H2 cleavage pathways.

Enantioselective Suzuki cross-couplings of unactivated 1-fluoro-1-haloalkanes: Synthesis of chiral β-, γ-, δ-, and ε-fluoroalkanes

The incorporation of fluorine atom into a stereogenic center is a highly challenging transformation with current methodologies offering access mainly to chiral α- and β-fluoroalkanes. In this article, the development of a novel general approach to constru

Organomediated Enantioselective 18F Fluorination for PET Applications

The first organomediated asymmetric 18F fluorination has been accomplished using a chiral imidazolidinone and [18F]N-fluorobenzenesulfonimide. The method provides access to enantioenriched 18F-labeled α-fluoroaldehydes (>90 % ee), which are versatile chiral 18F synthons for the synthesis of radiotracers. The utility of this process is demonstrated with the synthesis of the PET (positron emission tomography) tracer (2S,4S)-4-[18F]fluoroglutamic acid.

Efficient synthesis of secondary alkyl fluorides via suzuki cross-coupling reaction of 1-halo-1-fluoroalkanes

Organofluorine compounds have found extensive applications in various areas of science. Consequently, the development of new efficient and selective methods for their synthesis is an important goal in organic chemistry. Here, we present the first Suzuki c

COMPOUNDS THAT MODULATE INTRACELLULAR CALCIUM

Described herein are compounds and pharmaceutical compositions containing such compounds, which modulate the activity of store-operated calcium (SOC) channels. Also described herein are methods of using such SOC channel modulators, alone and in combinatio

Simple synthesis of optically active 2-fluoropropanoic acid and analogs of high enantiomeric purity

A very simple synthesis of optically active 2-fluoropropanoic acid 1 (R=CH3, R′=H) and analogs of high enantiomeric purity was developed using the sulfonates 2 of the corresponding optically active 2-hydroxycarboxylic esters and potassium fluor

Chemistry of Novel Compounds with Multifunctional Carbon Structure. 5. Molecular Design of Versatile Building Blocks for Aliphatic Monofluoro Molecules by Manipulation of Multifunctional Carbon Structure

Three kinds of doubly functionalized monofluoromethylene fragments, 1-fluoro-1-nitro-1-(phenylsulfonyl)alkanes (10), 2-fluoro-2-(phenylsulfonyl)alkanoic esters (11), and 2-fluoro-2-nitroalkanoic esters (12), potentially versatile building blocks for the general synthesis of various aliphatic monofluoro molecules, were prepared from the corresponding difunctional compounds 1-3 by monoalkylation (R) and selective fluorinations.The interconversion or reductive removal of each functional group in 10-12 followed by the introduction of the second alkyl groups (R') at the fluorine-bearing carbon atom was examined.Compounds 12 proved to be useful and practical building blocks for conversions to the various monofluoroalkanes 20-26.

The First Versatile and Practical Building Blocks Equivalent to the Synthon of Monofluoromethylene Dicarbanion

New monofluorinated synthons have been prepared.The use of α-fluoro-α-nitro carboxylic esters as versatile building blocks was demonstrated by their conversion to various monofluorinated compounds via fluoromethyl anion and fluoromethylene dianion equivalents.

Conformational Studies on 2-Fluoro-1,2-disubstituted Ethanes by NMR Spectroscopy. Influence of Electronegativity on Vicinal Proton-Proton and Fluorine-Proton Coupling Constants

The analysis of the ABKX spectra of thirteen compounds of the series RC(H-K)(F-X)C(H-A)(H-B)X gave the four vicinal proton-proton and fluorine-proton coupling constants.These coupling constants of conformationally mobile structures were used (i) to calcul

STEREOSPECIFICITY IN THE TRANSFORMATION OF α-AMINOACIDS INTO FLUOROACIDS

In the reaction of α-aminoacids with excess NaNO2 in polyhydrogen fluoride-pyridine, stereospecific substitution (i.e. retention of configuration) is observed with C6H11CH2CHNH2COOH, while a stereospecific rearrangment occurs in the case of phenylalanine.