3,4,5-Trifluoro-l-phenylalanine

Base Information

• Chemical Name: 3,4,5-Trifluoro-l-phenylalanine
• CAS No.: 646066-73-1
• Molecular Formula: C₉H₈F₃NO₂
• Molecular Weight: 219.163
• Hs Code.: 2922498590
• DSSTox Substance ID: DTXSID90426553
• Nikkaji Number: J1.410.330I
• Mol file: 646066-73-1.mol

Synonyms:3,4,5-trifluoro-l-phenylalanine;646066-73-1;L-(3,4,5-Trifluorophenyl)-alanine;(2s)-2-amino-3-(3,4,5-trifluorophenyl)propanoic acid;L-Phenylalanine, 3,4,5-trifluoro-;(S)-2-Amino-3-(3,4,5-trifluorophenyl)propanoic acid;SCHEMBL158047;DTXSID90426553;Phenylalanine, 3,4,5-trifluoro-;H-Phe(3,4,5-F3)-OH;MFCD03428422;AKOS012351061;AS-38511;CS-0170900;(S)-2-Amino-3-(3,4,5-trifluorophenyl)propanoicacid

Chemical Property of 3,4,5-Trifluoro-l-phenylalanine

Chemical Property:

• Vapor Pressure: 0.0004mmHg at 25°C
• Refractive Index: 1.518
• Boiling Point: 303.8 °C at 760 mmHg
• PKA: 2.12±0.30(Predicted)
• Flash Point: 137.5 °C
• PSA: 63.32000
• Density: 1.46 g/cm³
• LogP: 1.75860
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 219.05071298
• Heavy Atom Count: 15
• Complexity: 227

Purity/Quality:

98%min ^*data from raw suppliers

L-(3,4,5-Trifluorophenyl)-alanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 3,4,5-Trifluoro-l-phenylalanine

There total 4 articles about 3,4,5-Trifluoro-l-phenylalanine 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:

acetyl-DL-3,4,5-trifluorophenylalanine (324028-06-0) → 3,4,5-trifluoro-L-phenylalanine (646066-73-1,261952-26-5) + acetyl-D-3,4,5-trifluorophenylalanine (324028-12-8)

Guidance literature:

With sodium hydroxide; Aspergillus genus acylase; sodium acetate; In water; at 38 ℃; for 48h;

DOI:10.1246/bcsj.73.2531

Reference yield:

3,4,5-trifluorobenzyl bromide (220141-72-0) → 3,4,5-trifluoro-L-phenylalanine (646066-73-1,261952-26-5)

Guidance literature:

Multi-step reaction with 4 steps

1: Na; C₂H₅OH / 2 h / Heating

2: NaOH; HCl / methanol / 3 h / 40 °C

3: xylene / 2 h / 139 °C

4: NaOH; CH₃COONa; Aspergillus genus acylase / H₂O / 48 h / 38 °C

With hydrogenchloride; sodium hydroxide; ethanol; Aspergillus genus acylase; sodium acetate; sodium; In methanol; water; xylene;

DOI:10.1246/bcsj.73.2531

Reference yield:

diethyl 2-acetamido-2-(3,4,5-trifluorobenzyl)malonate (324027-94-3) → 3,4,5-trifluoro-L-phenylalanine (646066-73-1,261952-26-5)

Guidance literature:

Multi-step reaction with 3 steps

1: NaOH; HCl / methanol / 3 h / 40 °C

2: xylene / 2 h / 139 °C

3: NaOH; CH₃COONa; Aspergillus genus acylase / H₂O / 48 h / 38 °C

With hydrogenchloride; sodium hydroxide; Aspergillus genus acylase; sodium acetate; In methanol; water; xylene;

DOI:10.1246/bcsj.73.2531

upstream raw materials:

acetyl-DL-3,4,5-trifluorophenylalanine

3,4,5-trifluorobenzyl bromide

2-acetylamino-2-(3,4,5-trifluoro-benzyl)-malonic acid

diethyl 2-acetamido-2-(3,4,5-trifluorobenzyl)malonate

Refernces