151911-32-9

Basic information

• Product Name: (S)-3-AMINO-3-(2-FLUORO-PHENYL)-PROPIONIC ACID
• Synonyms: RARECHEM LK HC T305;(S)-3-AMINO-3-(2-FLUORO-PHENYL)-PROPIONIC ACID;H-BETA-PHE(2-F)-OH;H-D-BETA-HOMOPHG(2-F)-OH;H-D-PHG(2-F)-(C*CH2)OH;(S)-beta-2-Fluorophenylalanine;H-b-Phe(2-F)-OH;(betaS)-beta-amino-2-fluorobenzenepropanoic acid
• CAS NO: 151911-32-9
• Molecular Formula: C₉H₁₀FNO₂
• Molecular Weight: 183.18
• Product Categories: 3-Amino-3-phenylpropionic Acid Analogs;B-Amino
• Mol File: 151911-32-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 302.6 °C at 760 mmHg
• Flash Point: 136.8 °C
• Appearance: /
• Density: 1.289 g/cm³
• Vapor Pressure: 0.000434mmHg at 25°C
• Refractive Index: 1.554
• Storage Temp.: 2-8°C
• PKA: 3.67±0.10(Predicted)
• CAS DataBase Reference: (S)-3-AMINO-3-(2-FLUORO-PHENYL)-PROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-AMINO-3-(2-FLUORO-PHENYL)-PROPIONIC ACID(151911-32-9)
• EPA Substance Registry System: (S)-3-AMINO-3-(2-FLUORO-PHENYL)-PROPIONIC ACID(151911-32-9)

Safety Data

• Hazardous Substances Data: 151911-32-9(Hazardous Substances Data)

Usage

General Description

(S)-3-amino-3-(2-fluoro-phenyl)-propionic acid is a chemical compound with the molecular formula C9H10FNO2. It is a derivative of propionic acid and contains an amino group and a fluorine-substituted phenyl group. (S)-3-AMINO-3-(2-FLUORO-PHENYL)-PROPIONIC ACID is used in pharmaceutical research for its potential as a building block in the synthesis of various organic compounds. It may also have biological activity that could be relevant for drug development. Additionally, it can serve as a chiral auxiliary for the preparation of enantiomerically pure compounds. Its potential applications in drug discovery and organic synthesis make it an important compound in the field of medicinal and pharmaceutical chemistry.

InChI:InChI=1/C9H10FNO2/c10-7-4-2-1-3-6(7)8(11)5-9(12)13/h1-4,8H,5,11H2,(H,12,13)/t8-/m0/s1

Upstream product

• 889945-82-8 3-amino-3-(2-fluorophenyl)propionic acid methyl ester 
• 1393363-58-0 tert-butyl (3S,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-(2'-fluorophenyl)propanoate 
• 444108-95-6 tert-butyl (E)-3-(2'-fluorophenyl)prop-2-enoate 
• 1393363-72-8 tert-butyl (S)-3-amino-3-(2'-fluorophenyl)propanoate 
• 446-52-6 2-Fluorobenzaldehyde 
• 451-69-4 2-fluorocinnamic acid 
• 2629-55-2 2-fluoro-DL-phenylalanine 

Downstream Products

• 1213444-17-7 C₁₀H₁₂FNO₂ 
• 1307161-87-0 (S)-3-amino-3-(2-fluoro-phenyl)-propionic acid ethyl ester 
• 1397712-70-7 (S)-3-[5-(3-bromophenyl)-5,6,6-trimethyl-4,4-dioxo-5,6-dihydro-4H-4lambda6-[1,4,3]-oxathiazin-2-ylamino]-3-(2-fluorophenyl)propan-1-ol 
• 1397712-69-4 (S)-3-(2-fluorophenyl)-3-[5,6,6-trimethyl-4,4-dioxo-5-(3-pyrimidin-5-ylphenyl)-5,6-dihydro-4H-4lambda6-[1,4,3]-oxathiazin-2-ylamino]propan-1-ol 
• 1397712-67-2 (S)-3-(2-fluorophenyl)-3-{5-[3-(4-methanesulfonylpiperazin-1-yl)phenyl]-5,6,6-trimethyl-4,4-dioxo-5,6-dihydro-4H-4lambda6-[1,4,3]-oxathiazin-2-ylamino}propan-1-ol 
• 1397713-09-5 (S)-3-(2-fluorophenyl)-3-[5,6,6-trimethyl-5-(2'-methylbiphenyl-4-yl)-4,4-dioxo-5,6-dihydro-4H-4lambda6-[1,4,3]-oxathiazin-2-ylamino]propan-1-ol 
• 1397712-76-3 (S)-3-(5-biphenyl-4-yl-5,6,6-trimethyl-4,4-dioxo-5,6-dihydro-4H-4lambda6-[1,4,3]-oxathiazin-2-ylamino)-3-(2-fluorophenyl)propan-1-ol 
• 1397713-06-2 (S)-3-(9-biphenyl-4-yl-8,8-dioxo-2,5-dioxa-8lambda6-thia-7-azaspiro-[3,5]-non-6-en-6-ylamino)-3-(2-fluorophenyl)propan-1-ol 
• 1397749-97-1 (S)-3-[6,6-dimethyl-5-(4-morpholin-4-ylmethylphenyl)-4,4-dioxo-5,6-dihydro-4H-4lambda6-[1,4,3]-oxathiazin-2-ylamino]-3-(2-fluorophenyl)propan-1-ol 

Relevant articles and documents

Influence of the aromatic moiety in α- And β-arylalanines on their biotransformation with phenylalanine 2,3-aminomutase from: Pantoea agglomerans

In this study enantiomer selective isomerization of various racemic α- and β-arylalanines catalysed by phenylalanine 2,3-aminomutase from Pantoea agglomerans (PaPAM) was investigated. Both α- and β-arylalanines were accepted as substrates when the aryl moiety was relatively small, like phenyl, 2-, 3-, 4-fluorophenyl or thiophen-2-yl. While 2-substituted α-phenylalanines bearing bulky electron withdrawing substituents did not react, the corresponding substituted β-aryl analogues were converted rapidly. Conversion of 3- and 4-substituted α-arylalanines happened smoothly, while conversion of the corresponding β-arylalanines was poor or non-existent. In the range of pH 7-9 there was no significant influence on the conversion of racemic α- or β-(thiophen-2-yl)alanines, whereas increasing the concentration of ammonia (ammonium carbonate from 50 to 1000 mM) inhibited the isomerization progressively and decreased the amount of the by-product (i.e. (E)-3-(thiophen-2-yl)acrylic acid was detected). In all cases, the high ee values of the products indicated excellent enantiomer selectivity and stereospecificity of the isomerization except for (S)-2-nitro-α-phenylalanine (ee 92%) from the β-isomer. Substituent effects were rationalized by computational modelling revealing that one of the main factors controlling biocatalytic activity was the energy difference between the covalent regioisomeric enzyme-substrate complexes.

Asymmetric synthesis of β-fluoroaryl-β-amino acids

The conjugate addition of lithium (R)-N-benzyl-N-(α-methylbenzyl) amide to a range of β-fluoroaryl-α,β-unsaturated esters gave the corresponding β-amino esters with high diastereoselectivity and in good isolated yields. Sequential treatment of the resulta