2,3,4,5,6-Pentafluoro-L-phenylalanine

Base Information

• Chemical Name: 2,3,4,5,6-Pentafluoro-L-phenylalanine
• CAS No.: 34702-59-5
• Molecular Formula: C₉H₆F₅NO₂
• Molecular Weight: 255.144
• Hs Code.: 2922499990
• European Community (EC) Number: 630-779-8
• UNII: VJJ37GCZ42
• DSSTox Substance ID: DTXSID00375801
• Nikkaji Number: J694.750F
• Wikidata: Q27464395
• Mol file: 34702-59-5.mol

Synonyms:34702-59-5;(S)-2-Amino-3-(perfluorophenyl)propanoic acid;L-PENTAFLUOROPHE;2,3,4,5,6-PENTAFLUORO-L-PHENYLALANINE;138109-65-6;(2S)-2-amino-3-(2,3,4,5,6-pentafluorophenyl)propanoic acid;L-Pentafluorophenylalanine;L-Phenylalanine, 2,3,4,5,6-pentafluoro-;Pentafluorophenylalanine, L-;VJJ37GCZ42;(2S)-2-Azaniumyl-3-(2,3,4,5,6-pentafluorophenyl)propanoate;L-2,3,4,5,6-Pentafluorophenylalanine;D-2,3,4,5,6-Pentafluorophenylalanine;L-Phenylalanine,2,3,4,5,6-pentafluoro-, hydrochloride (9CI);(S)-2-Amino-3-(perfluorophenyl)propanoicacid;UNII-VJJ37GCZ42;H-PHE(F5)-OH;SCHEMBL158168;FLUORINATED PHENYLALANINE;DTXSID00375801;MFCD01860881;AKOS015890220;AC-5835;DS-3939;CS-0158433;P2085;C74787;A822352;Q27464395

Chemical Property of 2,3,4,5,6-Pentafluoro-L-phenylalanine

Chemical Property:

• Vapor Pressure: 0.00124mmHg at 25°C
• Melting Point: 254-257℃
• Refractive Index: 1.485
• Boiling Point: 286.3 °C at 760 mmHg
• PKA: 2.12±0.40(Predicted)
• Flash Point: 126.9 °C
• PSA: 40.54000
• Density: 1.609 g/cm³
• LogP: 2.59980
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Water Solubility.: Practically insoluble in water
• 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-L-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

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
• Uses: (S)-2-Amino-3-(perfluorophenyl)propanoic acid is used in the studies of fluorine containing dipeptides used in the diagnosis of cancer and other related conditions.

Technology Process of 2,3,4,5,6-Pentafluoro-L-phenylalanine

There total 22 articles about 2,3,4,5,6-Pentafluoro-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: 95.0%

(R,S)-N-phenylacetyl-pentafluorophenylalanine (151962-26-4) → 2',3',4',5',6'-Pentafluoro-L-phenylalanine (34702-59-5)

Guidance literature:

With water; E_. coli penicillin acylase; pH 7.6-7.7;

Reference yield: 51.0%

2,3,4,5,6-pentafluoro-trans-cinnamic acid (34234-46-3) → 2',3',4',5',6'-Pentafluoro-L-phenylalanine (34702-59-5)

Guidance literature:

With ammonium hydroxide; Petroselinum crispum phenylalanine ammonialyase (1U); at 37 ℃; for 24h; pH=10;

DOI:10.1002/1521-3765(20000915)6:18<3386::AID-CHEM3386>3.0.CO;2-5

Reference yield:

2,3,4,5,6-pentafluorotoluene (771-56-2) → (R,S)-pentafluoropenylalanine (3321-96-8,34702-59-5)

Guidance literature:

Multi-step reaction with 3 steps

1: Br₂ / CCl₄

2: (i) NaOEt, EtOH, (ii) /BRN= 647808/, DMF

3: aq. HCl

With hydrogenchloride; bromine; In tetrachloromethane;

DOI:10.1021/jo01255a011

upstream raw materials:

2-acetylamino-2-pentafluorophenylmethyl-malonic acid diethyl ester

(bromomethyl)pentafluorobenzene

2-acetylaminomalonic acid diethyl ester

2,3,4,5,6-pentafluorotoluene

Downstream raw materials:

C₁₇H₁₉F₅N₂O₂S₂

(S)-methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-(perfluorophenyl)propanamido)-3-(perfluorophenyl)propanoate

(S)-2-Amino-3-pentafluorophenyl-propionic acid methyl ester