1259973-37-9

Basic information

• Product Name: 2,4,6-TRIFLUORO-DL-PHENYLALANINE
• Synonyms: 2,4,6-TRIFLUORO-DL-PHENYLALANINE;DL-2,4,6-Trifluoro-Phe-OH [76932-42-8]
• CAS NO: 1259973-37-9
• Molecular Formula: C9H8F3NO2
• Molecular Weight: 219.16
• Mol File: 1259973-37-9.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,4,6-TRIFLUORO-DL-PHENYLALANINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-TRIFLUORO-DL-PHENYLALANINE(1259973-37-9)
• EPA Substance Registry System: 2,4,6-TRIFLUORO-DL-PHENYLALANINE(1259973-37-9)

Safety Data

• Hazardous Substances Data: 1259973-37-9(Hazardous Substances Data)

Usage

Molecular weight

211.16 g/mol

Structure

A phenyl ring with a side chain that contains an amino group (-NH2) and a carboxyl group (-COOH), with fluorine atoms at the 2, 4, and 6 positions on the phenyl ring.

Derivative of phenylalanine

A modified version of the natural amino acid phenylalanine.

Fluorinated compound

Contains three fluorine atoms.

Medicinal chemistry use

Used as a building block for creating novel pharmaceuticals and potential drug candidates.

Enhanced biological activity

The introduction of fluorine atoms can improve the compound's pharmacokinetic properties and increase its potency and selectivity.

Improved metabolic stability

The presence of fluorine atoms can enhance the compound's stability in the body, leading to better efficacy and longer-lasting effects.

Upstream product

• 324028-05-9 acetyl-DL-2,4,6-trifluorophenylalanine 
• 151411-98-2 2-(bromomethyl)-1,3,5-trifluorobenzene 
• 324027-99-8 2-acetylamino-2-(2,4,6-trifluoro-benzyl)-malonic acid 
• 324027-93-2 diethyl 2-acetamido-2-(2,4,6-trifluorobenzyl)malonate 
• 324028-11-7 acetyl-D-2,4,6-trifluorophenylalanine 

Relevant articles and documents

Exploration of the role of phenylalanine in the thrombin receptor tethered-ligand peptide by substitution with a series of trifluorophenylalanines

The thrombin receptor-tethered ligand SFLLRNP (abbreviation formed by one letter amino acid codes expressing Ser-Phe-Leu-Leu-Arg-Asn-Pro) consists of the Phe-2 residue essential for the receptor activation. In order to explore the molecular characteristics of this Phe-2-phenyl, a series of trifluorophenylalanines [(F3)Phe] was incorporated into this S/Phe/LLRNP for evaluation of their ability to induce the human platelet aggregation. A complete set of (F3)Phe in the L-configuration, namely, (2,3,4-F3)Phe, (2,3,5-F3)Phe, (2,3,6-F3)Phe, (2,4,5-F3)Phe, (2,4,6-F3)Phe, and (3,4,5-F3)Phe, was prepared from trifluorobenzyl bromides and diethyl acetamidomalonate. S/(2,3,4-F3)Phe/LLRNP was equipotent to S/Phe/LLRNP, while (2,4,5-F3)Phe-containing analog was almost twice as potent as those. (2,4,6-F3)Phe-analog exhibited about a half of the activity of S/Phe/LLRNP. (3,4,5-F3)Phe-, (2,3,5-F3)Phe-, and (2,3,6-F3)Phe-analogs were very weak. The analysis of these assay results suggested that Phe-2-phenyl of SFLLRNP is in the edge-to-face CH/π interaction with the receptor aromatic group, utilizing the Phe-2-phenyl edge along with benzene hydrogens at position 2-3 or 5-6. The computer-assisted semi-empirical molecular orbital calculations by MOPAC showed that the fluorine atom decreases the electron density of its ortho, meta, and para hydrogens, and thus increases their acidity more strongly in that order. All these suggested that H → F replacements reinforce the edge-to-face CH/π interaction to enhance biological activity. The H → F replacement on the Phe-phenyl group was found to render an effective structural examination; i.e., to identify the hydrogens in the CH/π interaction, and to intensify the CH/π interaction.