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

Base Information

• Chemical Name: (S)-3-Amino-3-(4-fluoro-phenyl)-propionic acid
• CAS No.: 151911-33-0
• Molecular Formula: C9H10FNO2
• Molecular Weight: 183.182
• Hs Code.: 2922498590
• European Community (EC) Number: 676-137-0
• DSSTox Substance ID: DTXSID60352557
• Nikkaji Number: J1.302.441C
• Mol file: 151911-33-0.mol

Synonyms:151911-33-0;(s)-3-amino-3-(4-fluorophenyl)propionic acid;(S)-3-Amino-3-(4-fluoro-phenyl)-propionic acid;(3S)-3-amino-3-(4-fluorophenyl)propanoic acid;(S)-3-Amino-3-(4-fluorophenyl)propanoic acid;(S)-beta-(p-Fluorophenyl)alanine;(s)-3-(p-fluorophenyl)-beta-alanine;(s)-3-amino-3-(4-fluoro-phenyl)propionic acid;(s)-beta-4-fluorophenylalanine;h-beta-phe(4-f)-oh;h-d-phg(4-f)-(c*ch2)oh;(s)-4-fluoro-beta-phenylalanine;(s)-b-(p-fluorophenyl)-b-alanine;S-3-Amino-3-(4-fluoro-phenyl)-propionic acid;SCHEMBL3338961;DTXSID60352557;CPGFMWPQXUXQRX-QMMMGPOBSA-N;H-D-Phg(4-F)-(C#CH2)OH;MFCD03840458;AKOS016843170;AC-6620;AS-37739;CS-0170972;(S)-3-Amino-3-(4-fluorophenyl)propanoicacid;(s)-3-amino-3-(4-fluorophenyl)propionicacid;EN300-105899;(s)-3-amino-3-(4-fluoro-phenyl)-propanoic acid;(S)-3-(P-FLUOROPHENYL)-BETA-ALANINE

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

Chemical Property:

• Vapor Pressure: 0.000287mmHg at 25°C
• 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.: 2-8°C(protect from light)
• 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:

99.5% ^*data from raw suppliers

(S)-3-Amino-3-(4-fluorophenyl)propionicAcid ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

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

There total 14 articles about (S)-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: 96.0%

tert-butyl (S)-3-amino-3-(4'-fluorophenyl)propanoate (1393363-74-0) → (S)-β-amino-β-(4-fluorophenyl)propionic acid (151911-33-0)

Guidance literature:

tert-butyl (S)-3-amino-3-(4'-fluorophenyl)propanoate; With hydrogenchloride; water; for 6h; Reflux;

With ammonium hydroxide; In water;

DOI:10.1016/j.tetasy.2012.07.001

Reference yield: 46.0%

n-propyl 3-amino-3-(4-fluorophenyl)propionate → C12H16FNO2 + (S)-β-amino-β-(4-fluorophenyl)propionic acid (151911-33-0)

Guidance literature:

With Amano Lipase PS; water; In tert-butyl methyl ether; for 15h; pH=8.2; optical yield given as %ee; enantioselective reaction; Enzymatic reaction;

DOI:10.1021/op200084g

Reference yield:

4-Fluorophenylalanine (51-65-0) → (R)-4-fluorophenylalanine (18125-46-7) + (E)-4-fluorocinnamic acid (459-32-5) + (S)-β-amino-β-(4-fluorophenyl)propionic acid (151911-33-0)

Guidance literature:

With phenylalanine 2,3-aminomutase from Pantoea agglomerans; ammonium carbonate; at 20 ℃; for 20h; pH=8; enantioselective reaction; Enzymatic reaction;

DOI:10.1039/c6ra02964g

upstream raw materials:

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

3-amino-3-(4-fluorophenyl)propanoic acid

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

tert-butyl (3S,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-(4'-fluorophenyl)propanoate

Downstream raw materials:

(3S)-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-(4-fluorophenol)propanoic acid

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、 Li, Dengchao,Ji, Lilian,Wang, Xinfeng,Wei, Dongzhi. "Enantioselective acylation of β-phenylalanine acid and its derivatives catalyzed by penicillin G acylase from alcaligenes faecalis". . p. 207 - 216. Retrieved 2013/04/23.