2-Trifluoromethyl-DL-Phenylalanine is a non-natural phenylalanine analogue bearing a trifluoromethyl substituent at the 2-position of the α-carbon and a phenyl side chain, existing as a DL (racemic) mixture. The molecule contains both an amino group and a carboxyl group characteristic of amino acid frameworks, with the 2-trifluoromethyl substitution altering steric and electronic properties relative to unmodified phenylalanine while maintaining a chiral center consistent with the stated DL stereochemical form. It is used in peptide and amino acid derivative synthesis and in structure-activity or labeling studies where fluorinated, electronically modified amino acid residues help probe conformational effects, binding interactions, or analytical behavior in chemical biology and biomaterials research.
CAT No: CP16603
2-Trifluoromethyl-DL-Phenylalanine is a DL (racemic) phenylalanine analog bearing a trifluoromethyl substituent at the 2-position of the aromatic ring, providing a strongly electron-withdrawing, metabolically robust aryl motif. This non-natural amino acid building block is used in medicinal chemistry and peptidomimetic development where fluorinated aromatic side chains are leveraged to tune physicochemical properties and structure-activity relationships. As a free amino acid (or amino-acid salt form, depending on the supplied grade), it offers the standard amino acid functionality for incorporation into synthetic sequences and for conversion into protected derivatives for downstream coupling.
1. Peptidomimetic Building Blocks
2-Trifluoromethyl-DL-Phenylalanine is used by medicinal chemistry and chemical biology teams to construct peptidomimetic scaffolds and fluorinated amino acid residues within synthetic peptides or peptide-like ligands. The trifluoromethyl-substituted phenyl side chain is a common strategy for modulating aromatic electronics and improving the stability of aryl-containing motifs in structure-activity relationship (SAR) studies. Researchers typically employ this building block when they need a phenylalanine-derived residue that introduces a distinct fluorinated pharmacophore while retaining the amino acid backbone for coupling into larger constructs.
2. Medicinal Chemistry SAR Studies
2-Trifluoromethyl-DL-Phenylalanine supports SAR workflows focused on evaluating how fluorinated aryl substitution impacts binding-site interactions and overall molecular properties in lead optimization. Medicinal chemistry groups incorporate this residue into analog series to systematically vary steric and electronic character around an aromatic side chain, using the trifluoromethyl group as a defined substituent rather than a generic "fluorinated" motif. Because the material is provided as a DL mixture, it is frequently selected for parallel library synthesis and early-stage analog screening where stereochemical resolution is handled later if required.
3. Protected Amino Acid Derivative Synthesis
2-Trifluoromethyl-DL-Phenylalanine is commonly converted into protected amino acid derivatives for use in peptide synthesis and modular intermediate assembly. Synthetic chemistry teams rely on its amino acid functionality to prepare coupling-ready forms (for example, protected at the amine and/or carboxylate activation states) that can be integrated into solution-phase or solid-phase workflows for assembling fluorinated peptide segments and intermediates. This makes the compound a practical starting point for generating 2-trifluoromethyl phenylalanine-containing fragments used in custom peptide manufacturing research and in the preparation of defined, reproducible analogs for downstream characterization.
4. Pharmaceutical Intermediate Development
2-Trifluoromethyl-DL-Phenylalanine is used as a fluorinated amino acid intermediate in the development of specialty chemical building blocks for medicinal chemistry programs. Process and development chemists incorporate this motif into larger intermediates that later feed into final active-ingredient candidates or advanced lead structures, where the trifluoromethyl-substituted aromatic ring serves as a stable, property-defining element. Industrial and contract synthesis teams value the compound as a standardized starting material for producing consistent fluorinated aryl-containing intermediates that support scalable analog generation and method development.
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