2-Trifluoromethyl-L-Phenylalanine is a fluorinated, non-proteinogenic amino acid derivative classified as an α-amino acid, featuring an L-configuration at the α-carbon and a phenyl side chain bearing a trifluoromethyl substituent at the 2-position. The molecule contains a free α-amino group and a carboxyl functional group while the aromatic ring carries the electron-withdrawing CF3 group, which modifies side-chain polarity and steric/electronic characteristics relative to phenylalanine. In synthetic and chemical biology workflows, it is used as a defined building block for peptide and peptidomimetic synthesis and for structure-activity or labeling studies where fluorinated aromatic residues help tune physicochemical properties and enable analytical differentiation.
CAT No: CP16601
CAS No:119009-47-1
Synonyms/Alias:119009-47-1;2-Trifluoromethyl-L-Phenylalanine;2-(Trifluoromethyl)-L-phenylalanine;(S)-2-Amino-3-(2-(trifluoromethyl)phenyl)propanoic acid;L-2-Trifluoromethylphenylalanine;(2S)-2-amino-3-[2-(trifluoromethyl)phenyl]propanoic acid;L-Phenylalanine, 2-(trifluoromethyl)-;(2S)-2-azaniumyl-3-[2-(trifluoromethyl)phenyl]propanoate;L-2-Trifluoromethylphe;2-(Trifluoromethyl)-L-phenyalanine;MFCD00077615;SCHEMBL42976;DTXSID20375803;AKOS012010567;AC-5860;CS-W012930;HY-W012214;JS-4130;F52526;(S)-2-Amino-3-(2-(trifluoromethyl)phenyl)propanoicacid;2-(Trifluoromethyl)-L-phenylalanine, >=98.0% (TLC);
2-Trifluoromethyl-L-Phenylalanine is a fluorinated, non-natural amino acid featuring an L-configuration at the alpha carbon and a phenyl ring substituted with a trifluoromethyl group at the 2-position. Its strongly electron-withdrawing CF3 substituent makes it a valuable building block for medicinal chemistry and peptide lead optimization, where aromatic electronics and hydrophobicity are tuned to probe structure-activity relationships. Researchers also use this compound as a defined fluorinated amino acid intermediate to introduce CF3-bearing aromatic residues into larger synthetic targets.
1. Peptide Lead Optimization
2-Trifluoromethyl-L-Phenylalanine is used by peptide chemistry groups to incorporate a CF3-substituted phenylalanine residue into short peptides and peptidomimetic scaffolds. The 2-CF3 substitution provides a convenient handle for modulating aromatic electronics and lipophilicity while maintaining an amino-acid-like geometry for downstream coupling strategies. This makes it a practical choice for structure-activity relationship studies in custom peptide synthesis, where the goal is to compare analogs that differ specifically at the aromatic side chain.
2. Medicinal Chemistry SAR Building Block
2-Trifluoromethyl-L-Phenylalanine is frequently selected by medicinal chemistry and drug discovery teams as a fluorinated amino acid building block for preparing CF3-containing intermediates and peptidomimetic fragments. The CF3 group is commonly leveraged to tune physicochemical properties and to create analog series that systematically vary aromatic substitution patterns. In workflow terms, this compound supports the rapid generation of defined derivatives for SAR campaigns, enabling chemists to evaluate how a 2-trifluoromethyl aromatic motif influences binding hypotheses and overall molecular properties.
3. Pharmaceutical Intermediate Development
2-Trifluoromethyl-L-Phenylalanine serves as a research-grade intermediate for the synthesis of fluorinated aromatic derivatives used in pharmaceutical intermediate pipelines. Process and development chemists rely on well-defined, stereochemically consistent amino acid inputs to construct CF3-substituted motifs that appear in many bioactive lead classes and specialty chemical targets. By providing a direct entry point to a 2-trifluoromethyl phenylalanine framework, it helps streamline the preparation of downstream building blocks used in route scouting and analog manufacturing.
4. Chiral Synthesis Reference Material
2-Trifluoromethyl-L-Phenylalanine is also used in chiral chemistry workflows where a defined L-amino acid stereocenter is required as a reference input for method development and intermediate verification. Enantiopure fluorinated amino acid derivatives are particularly valuable when researchers need consistent stereochemical material to compare coupling outcomes, purification behavior, or identity confirmation across analog series. This makes the compound useful for analytical method development and for supporting reproducible synthesis planning in fluorinated building block programs.
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