(R)-3-Amino-3-(4-fluoro-phenyl)-propionic acid

Base Information

• Chemical Name: (R)-3-Amino-3-(4-fluoro-phenyl)-propionic acid
• CAS No.: 151911-23-8
• Molecular Formula: C9H10FNO2
• Molecular Weight: 183.182
• Hs Code.: 2922499990
• European Community (EC) Number: 674-811-9
• Nikkaji Number: J1.302.440E
• Mol file: 151911-23-8.mol

Synonyms:151911-23-8;(r)-3-(p-fluorophenyl)-beta-alanine;(R)-3-Amino-3-(4-fluoro-phenyl)-propionic acid;(R)-3-amino-3-(4-fluorophenyl)propanoic acid;(3R)-3-amino-3-(4-fluorophenyl)propanoic acid;(R)-3-Amino-3-(4-fluorophenyl)propanoicacid;(r)-3-amino-3-(4-fluoro-phenyl)propionic acid;h-d-beta-phe(4-f)-oh;h-phg(4-f)-(c*ch2)oh;(r)-beta-4-fluorophenylalanine;(r)-beta-(p-fluorophenyl)alanine;(r)-3-amino-3-(4-fluorophenyl)propionic acid;R-3-Amino-3-(4-fluoro-phenyl)-propionic acid;(r)-3-amino-3-(4-fluoro-phenyl)-propanoic acid;SCHEMBL2764337;(R)- -(p-Fluorophenyl)alanine;(r)-4-fluoro-beta-phenylalanine;H-Phg(4-F)-(C#CH2)OH;(r)-b-(p-fluorophenyl)-b-alanine;MFCD03840459;AKOS010393436;AKOS015995203;AC-6619;AS-37740;A3342;CS-0170971;EN300-317887;(R)-3-Amino-3-(4-fluorophenyl)-propionic acid

Chemical Property of (R)-3-Amino-3-(4-fluoro-phenyl)-propionic acid

Chemical Property:

• Vapor Pressure: 0.000287mmHg at 25°C
• Melting Point: 245-247 °C(Solv: water (7732-18-5); acetone (67-64-1))
• Refractive Index: 1.554
• Boiling Point: 308.829 °C at 760 mmHg
• PKA: 3.66±0.10(Predicted)
• Flash Point: 140.575 °C
• PSA: 63.32000
• Density: 1.29 g/cm³
• LogP: 2.00050
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 183.06955672
• Heavy Atom Count: 13
• Complexity: 179

Purity/Quality:

99% ^*data from raw suppliers

(2R)-3-Amino-2-(4-fluorophenyl)propanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(CC(=O)O)N)F
• Isomeric SMILES: C1=CC(=CC=C1[C@@H](CC(=O)O)N)F

Technology Process of (R)-3-Amino-3-(4-fluoro-phenyl)-propionic acid

There total 14 articles about (R)-3-Amino-3-(4-fluoro-phenyl)-propionic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

4-fluorocinnamic acid (459-32-5,14290-66-5,14290-86-9) → L-4-fluorophenylalanine (1132-68-9) + (R)-β-amino-β-(4-fluorophenyl)propionic acid (151911-23-8)

Guidance literature:

With ammonia; at 25 ℃; pH=9; regioselective reaction; Kinetics; aq. buffer; Enzymatic reaction;

DOI:10.1002/anie.201106372

Reference yield: 73.0%

β-(N-phenylacetylamino)-β-(4-fluorophenyl)propionic acid (171002-17-8) → (R)-β-amino-β-(4-fluorophenyl)propionic acid (151911-23-8)

Guidance literature:

With potassium hydroxide; Ambient temperature; penicillin acylase (EC 3.5.1.11), pH 7.5;

DOI:10.1016/0957-4166(95)00204-3

Reference yield: 48.0%

(+/-)-4-(4-fluorophenyl)-2-azetidinone (930769-46-3) → (S)-4-(4-fluorophenyl)-2-azetidinone (930769-51-0) + (R)-β-amino-β-(4-fluorophenyl)propionic acid (151911-23-8)

Guidance literature:

With CAL-B (lipase B from Candida antarctica); water; In isopropyl alcohol; at 60 ℃; for 13h;

DOI:10.1002/adsc.200505434

upstream raw materials:

β-(N-phenylacetylamino)-β-(4-fluorophenyl)propionic acid

3-amino-3-(4-fluorophenyl)propionic acid ethyl ester

(+/-)-4-(4-fluorophenyl)-2-azetidinone

L-4-fluorophenylalanine

Refernces

• 1、 Varga, Andrea,Bánóczi, Gergely,Nagy, Botond,Bencze, László Csaba,To?a, Monica Ioana,Gellért, ákos,Irimie, Florin Dan,Rétey, János,Poppe, László,Paizs, Csaba. "Influence of the aromatic moiety in α- And β-arylalanines on their biotransformation with phenylalanine 2,3-aminomutase from: Pantoea agglomerans". . p. 56412 - 56420. Retrieved 2016/07/06.
• 2、 Wu, Bian,Szymanski, Wiktor,Wybenga, Gjalt G.,Heberling, Matthew M.,Bartsch, Sebastian,Dewildeman, Stefaan,Poelarends, Gerrit J.,Feringa, Ben L.,Dijkstra, Bauke W.,Janssen, Dick B.. "Mechanism-inspired engineering of phenylalanine aminomutase for enhanced β-regioselective asymmetric amination of cinnamates". supporting information; experimental part. p. 482 - 486. Retrieved 2012/03/22.