(R)-2-Amino-3-(perfluorophenyl)propanoic acid

Base Information

• Chemical Name: (R)-2-Amino-3-(perfluorophenyl)propanoic acid
• CAS No.: 40332-58-9
• Molecular Formula: C₉H₆F₅NO₂
• Molecular Weight: 255.144
• Hs Code.: 2922499990
• UNII: 05KD6AHA6F
• Nikkaji Number: J2.211.712B
• Mol file: 40332-58-9.mol

Synonyms:40332-58-9;(R)-2-Amino-3-(perfluorophenyl)propanoic acid;D-PENTAFLUOROPHE;D-Pentafluorophenylalanine;2,3,4,5,6-PENTAFLUORO-D-PHENYLALANINE;(2R)-2-AMINO-3-(2,3,4,5,6-PENTAFLUOROPHENYL)PROPANOIC ACID;Pentafluorophenylalanine, D-;05KD6AHA6F;D-Phenylalanine, 2,3,4,5,6-pentafluoro-;D-2,3,4,5,6-Pentafluorophenylalanine;(R)-2-Amino-3-(perfluorophenyl)propanoicacid;UNII-05KD6AHA6F;SCHEMBL4626004;MFCD01860872;AKOS016843740;AC-5836;DS-3941;3-(PENTAFLUOROPHENYL)-D-ALANINE;CS-0186124;N12370;(2R)-2-Amino-3-(pentafluorophenyl)propionic acid;A825057;(R)-2-Amino-3-pentafluorophenyl-propionic acid (H-D-Phe(F5)-OH)

Chemical Property of (R)-2-Amino-3-(perfluorophenyl)propanoic acid

Chemical Property:

• Boiling Point: 286.3 °C at 760 mmHg
• PKA: 2.12±0.40(Predicted)
• Flash Point: 126.9 °C
• PSA: 63.32000
• Density: 1.609 g/cm³
• LogP: 2.03680
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 255.03186924
• Heavy Atom Count: 17
• Complexity: 277

Purity/Quality:

97% ^*data from raw suppliers

Pentafluoro-D-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C1=C(C(=C(C(=C1F)F)F)F)F)C(C(=O)O)N
• Isomeric SMILES: C(C1=C(C(=C(C(=C1F)F)F)F)F)[C@H](C(=O)O)N

Technology Process of (R)-2-Amino-3-(perfluorophenyl)propanoic acid

There total 6 articles about (R)-2-Amino-3-(perfluorophenyl)propanoic 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:

(bromomethyl)pentafluorobenzene (1765-40-8) → (2R)-2-amino-3-(2,3,4,5,6-pentafluorophenyl)propanoic acid (40332-58-9,34702-59-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / LDA / tetrahydrofuran; hexane / from -60 degC to room temp.

2: 1.) trifluoroacetic acid; 2.) DOWEX 50 Wx 8 cation exchange resin / 1.) CH₂Cl₂, overnight; 2.) AcOH, 0.75 N HCl, 100 degC, 18 h

With DOWEX 50 Wx 8 cation exchange resin; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; hexane;

DOI:10.1016/S0040-4020(01)86036-1

Reference yield:

(R,S)-pentafluoropenylalanine (3321-96-8,34702-59-5) → (2R)-2-amino-3-(2,3,4,5,6-pentafluorophenyl)propanoic acid (40332-58-9,34702-59-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / NaHCO₃ / acetone; H₂O / 3 h / -10 - 25 °C

3: 6 N aq. HCl / 7 h / 70 - 80 °C

With hydrogenchloride; sodium hydrogencarbonate; In water; acetone;

Reference yield:

(R)-N-phenylacetyl-pentafluorophenylalanine → (2R)-2-amino-3-(2,3,4,5,6-pentafluorophenyl)propanoic acid (40332-58-9,34702-59-5)

Guidance literature:

With hydrogenchloride; at 70 - 80 ℃; for 7h; Yield given;

upstream raw materials:

(2R,5R)-2-t-butyl-1-t-butyloxycarbonyl-3-methyl-5-pentafluorobenzyl-4-imidazolidinone

(R,S)-pentafluoropenylalanine

(R,S)-N-phenylacetyl-pentafluorophenylalanine

(bromomethyl)pentafluorobenzene