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
• Article Data: 11

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

• 141022-92-6 (4S,5R)-3-(2-Fluoro-2-phenyl-acetyl)-4-methyl-5-phenyl-oxazolidin-2-one 
• 103-80-0 phenylacetyl chloride 
• 1578-63-8 d'acide 2-fluoro-2-phenyl acetique 
• 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 

Downstream Products

• 133175-32-3 (R)-2-((R)-2-Fluoro-2-phenyl-acetylamino)-3-methyl-butyric acid methyl ester 
• 133175-48-1 (S)-2-((R)-2-Fluoro-2-phenyl-acetylamino)-3-methyl-butyric acid methyl ester 
• 133175-58-3 (R)-2-Fluoro-2-phenyl-N-((R)-phenyl-p-tolyl-methyl)-acetamide 
• 133175-66-3 (R)-2-Fluoro-2-phenyl-N-((S)-phenyl-p-tolyl-methyl)-acetamide 
• 133175-50-5 (S)-((R)-2-Fluoro-2-phenyl-acetylamino)-phenyl-acetic acid methyl ester 
• 133175-34-5 (R)-((R)-2-Fluoro-2-phenyl-acetylamino)-phenyl-acetic acid methyl ester 
• 133175-33-4 (R)-2-((R)-2-Fluoro-2-phenyl-acetylamino)-3-phenyl-propionic acid methyl ester 
• 133175-49-2 (S)-2-((R)-2-Fluoro-2-phenyl-acetylamino)-3-phenyl-propionic acid methyl ester 
• 133175-56-1 (R)-N-[(R)-(4-Bromo-phenyl)-phenyl-methyl]-2-fluoro-2-phenyl-acetamide 
• 133175-65-2 (R)-N-[(S)-(4-Bromo-phenyl)-phenyl-methyl]-2-fluoro-2-phenyl-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 
• 133175-41-4 (R)-2-Fluoro-2-phenyl-N-((S)-1,2,2-trimethyl-propyl)-acetamide 
• 133175-25-4 (R)-2-Fluoro-2-phenyl-N-((R)-1,2,2-trimethyl-propyl)-acetamide 

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.

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