63818-94-0

Basic information

• Product Name: Benzeneacetic acid, a-fluoro-, (R)-
• CAS NO: 63818-94-0
• Molecular Formula: C8H7FO2
• Molecular Weight: 154.141
• Mol File: 63818-94-0.mol

Chemical Properties

• CAS DataBase Reference: Benzeneacetic acid, a-fluoro-, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzeneacetic acid, a-fluoro-, (R)-(63818-94-0)
• EPA Substance Registry System: Benzeneacetic acid, a-fluoro-, (R)-(63818-94-0)

Safety Data

• Hazardous Substances Data: 63818-94-0(Hazardous Substances Data)

Upstream product

• 1578-63-8 d'acide 2-fluoro-2-phenyl acetique 
• 103-80-0 phenylacetyl chloride 
• 141022-85-7 (4S,5R)-4-methyl-5-phenyl-3-phenylacetyloxazolidin-2-one 
• 2882-19-1 ethyl 2-phenyl-2-bromoacetate 
• 643-77-6 fluoro-phenyl-acetic acid ethyl ester 
• 2802-98-4 diethyl 2-fluoro-2-phenylmalonate 
• 4870-65-9 2-bromophenylacetic acid 
• 10036-43-8 α-(Fluorophenyl)acetonitrile 
• 949897-58-9 C₁₁H₁₀NSO₂F 
• 2835-06-5 phenylglycin 
• 141022-92-6 (4S,5R)-3-(2-Fluoro-2-phenyl-acetyl)-4-methyl-5-phenyl-oxazolidin-2-one 

Downstream Products

• 133175-53-8 (R)-2-Fluoro-2-phenyl-N-((S)-1-p-tolyl-ethyl)-acetamide 
• 133175-37-8 (R)-2-Fluoro-2-phenyl-N-((R)-1-p-tolyl-ethyl)-acetamide 
• 133175-43-6 (R)-2-Fluoro-2-phenyl-N-((S)-1-phenyl-propyl)-acetamide 
• 133175-27-6 (R)-2-Fluoro-2-phenyl-N-((R)-1-phenyl-propyl)-acetamide 
• 133175-54-9 (R)-2-Fluoro-N-[(S)-1-(4-methoxy-phenyl)-ethyl]-2-phenyl-acetamide 
• 133175-38-9 (R)-2-Fluoro-N-[(R)-1-(4-methoxy-phenyl)-ethyl]-2-phenyl-acetamide 
• 133175-30-1 (R)-2-((R)-2-Fluoro-2-phenyl-acetylamino)-propionic acid methyl ester 
• 133175-46-9 (S)-2-((R)-2-Fluoro-2-phenyl-acetylamino)-propionic acid methyl ester 
• 116046-15-2 (R)-Fluoro-phenyl-acetic acid (S)-2-(2-methoxy-phenoxy)-1-phenyl-ethyl ester 
• 116046-15-2 (R)-Fluoro-phenyl-acetic acid (R)-2-(2-methoxy-phenoxy)-1-phenyl-ethyl ester 
• 128864-66-4 (R)-((R)-2-Fluoro-2-phenyl-acetoxy)-phenyl-acetic acid methyl ester 
• 128864-67-5 (S)-((R)-2-Fluoro-2-phenyl-acetoxy)-phenyl-acetic acid methyl ester 
• 128864-59-5 (R)-Fluoro-phenyl-acetic acid (S)-2-methyl-1-phenyl-propyl ester 
• 128864-58-4 (R)-Fluoro-phenyl-acetic acid (R)-2-methyl-1-phenyl-propyl ester 

Relevant articles and documents

Semirational Design of Fluoroacetate Dehalogenase RPA1163 for Kinetic Resolution of α-Fluorocarboxylic Acids on a Gram Scale

Here the synthetic utility of fluoroacetate dehalogenase RPA1163 is explored for the production of enantiomerically pure (R)-α-fluorocarboxylic acids and (R)-α-hydroxylcarboxylic acids via kinetic resolution of racemic α-fluorocarboxylic acids. While wild-type (WT) RPA1163 shows high thermostability and fairly wide substrate scope, many interesting yet poorly or moderately accepted substrates exist. In order to solve this problem and to develop upscaled production, in silico calculations and semirational mutagenesis were employed. Residue W185 was engineered to alanine, serine, threonine, or asparagine. The two best mutants, W185N and W185T, showed significantly improved performance in the reactions of these substrates, while in silico calculations shed light on the origin of these improvements. Finally, 10 α-fluorocarboxylic acids and 10 α-hydroxycarboxylic acids were prepared on a gram scale via kinetic resolution enabled by WT, W185T, or W185N. This work expands the biocatalytic toolbox and allows a deep insight into the fluoroacetate dehalogenase catalyzed C-F cleavage mechanism.

Chiral alpha-selenofluorophenyl acetate compound as well as preparation and application thereof

The invention discloses a novel chiral compound with an alpha-selenofluorophenyl acetate structure, and a preparation method and application thereof. The structure of the novel chiral compound is shown in the attached figure. The preparation method of the novel chiral compound is characterized in that the optical pure alpha-fluorophenylacetate is split and synthesized at high efficiency by using optical pure chloramphenicol amine as a splitting agent, and then is esterified with diphenyl diselenide. The novel chiral compound is used as a chiral derivative reagent to detect the absolute configuration of multiple chiral compounds of chiral amine, alkamine, amino-acid ester and the like, and is characterized in that the nuclear-magnetic fluorine spectrum of the derivative reacted by a chiralprimer and (R)-alpha-selenofluorophenyl acetate and (S)-alpha-selenofluorophenyl acetate is tested, and the absolute configuration of the chiral primer is judged by contrasting the chemical displacement of alpha-F of the chiral primer under two conditions. The preparation method has the advantages that the reagent synthesis is simple, the operation is convenient, the chemical displacement difference is large, and the method is a simple and efficient method for judging the absolute configuration.

Investigating Substrate Scope and Enantioselectivity of a Defluorinase by a Stereochemical Probe

The possibility of a double Walden inversion mechanism of the fluoracetate dehalogenase FAcD (RPA1163) has been studied by subjecting rac-2-fluoro-2-phenyl acetic acid to the defluorination process. This stereochemical probe led to inversion of configuration in a kinetic resolution with an extremely high selectivity factor (E > 500), showing that the classical mechanism involving SN2 reaction by Asp110 pertains. The high preference for the (S)-substrate is of synthetic value. Wide substrate scope of RPA1163 in such hydrolytic kinetic resolutions can be expected because the reaction of the even more sterically demanding rac-2-fluoro-2-benzyl acetic acid proceeded similarly. Substrate acceptance and stereoselectivity were explained by extensive molecular modeling (MM) and molecular dynamics (MD) computations. These computations were also applied to fluoroacetic acid itself, leading to further insights.

Asymmetric fluorination of α-aryl acetic acid derivatives with the catalytic system NiCl2-binap/R3SiOTf/2,6-lutidine

(Chemical Equation Presented) Not binary, but trinary: A binary system consisting of Ni(OTf)2-binap complex and 2,6-lutidine failed to promote the asymmetric fluorination of ester equivalents. However, upon the addition of a substoichiometric a

Enantioselective hydrolysis of (RS)-2-fluoroarylacetonitriles using nitrilase from Arabidopsis thaliana

The enzymatic resolution of 2-fluoroarylacetonitriles (RS)-3 using nitrilase from the plant Arabidopsis thaliana is described. Racemic 2-fluoronitriles 3 are easily accessible from O-silylated aromatic cyanohydrins 2 by reaction with DAST. The nitriles (RS)-3 were hydrolysed with the nitrilase as a catalyst, not to the expected 2-fluoroarylacetic acids but to the corresponding (R)-2-fluoroarylacetamides (R)-5 as the main products. After optimization of reaction conditions (pH 9, 7°C), the enantiomeric excesses of (R)-5a,c and f (R=H, 3-Me, 3-OMe) could be improved to >99% by one recrystallization. The acid catalysed hydrolysis of (R)-5a,5c and 5f afforded the corresponding (R)-2-fluoroarylacetic acids (R)-4a,4c and 4f without racemization.

Preparative-scale enzyme-catalyzed synthesis of (R)-α-fluorophenylacetic acid

A preparative-scale asymmetric synthesis of (R)-α-fluorophenylacetic acid, a useful chiral derivatizing reagent, is described. Starting from ethyl α-bromophenylacetate, α-fluorophenylmalonic acid dipotassium salt was prepared in three steps (54% yield), including nucleophilic substitution by the fluoride ion as the keystep. Both the purified form and crude preparation of arylmalonate decarboxylase in E. coli worked well on this substrate, and (R)-α-flurophenylacetic acid (>99% e.e.) was prepared in a quantitative yield.

Diastereoselective fluorination of chiral imide enolates using N-Fluoro-O-Benzenedisulfonimide (NFOBS)

α-Fluoro acids (78-90% ee) and β-fluoro alcohols (89->95%ee) of well defined stereochemistry are prepared via the diastereoselective fluorination of chiral imide enolates with NFOBS (3).

Microbial asymmetric decarboxylation of fluorine-containing arylmalonic acid derivatives

α-Methyl-α-(trifluoromethylphenyl)malonic acids have been incubated with Alcaligenes bronchisepticus to afford optically active α-arylpropionic acids.Generally, the chemical and optical yields of the reaction products were higher when the substituents on the aromatic ring were strongly electron-withdrawing.Decarboxylation of α-fluoro-α-phenylmalonic acid with the aid of the same bacterium afforded optically active α-fluoro-α-phenylacetic acid.