Boc-2-Trifluoromethyl-L-Phenylalanine is a Boc-protected, L-configured amino acid derivative belonging to the phenylalanine family, featuring a phenyl side chain substituted at the 2-position with a trifluoromethyl group. The molecule contains a carbamate-protected amino group (Boc) and a free carboxyl group, while the electron-withdrawing CF3 substituent on the aromatic ring modulates side-chain polarity and chemical behavior during peptide coupling. In peptide chemistry and structure-activity studies, this protected analogue is used as a building block to introduce the trifluoromethylated phenylalanine motif into peptide sequences and related amino acid derivatives, supporting controlled chemoselectivity at the amino functionality during stepwise synthesis.
CAT No: CP16604
CAS No:167993-21-7
Synonyms/Alias:167993-21-7;Boc-2-(trifluoromethyl)-L-phenylalanine;Boc-2-Trifluoromethyl-L-Phenylalanine;(S)-2-((tert-Butoxycarbonyl)amino)-3-(2-(trifluoromethyl)phenyl)propanoic acid;BOC-L-2-TRIFLUOROMETHYLPHE;Boc-Phe(2-CF3)-OH;L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-2-(trifluoromethyl)-;(2S)-2-[(tert-butoxycarbonyl)amino]-3-[2-(trifluoromethyl)phenyl]propanoic acid;SCHEMBL1270065;MFCD01862945;AKOS015836662;AKOS015890219;AC-9069;PS-12022;A50141;Boc-Phe(2-CF3)-OH, >=98.0% (TLC);N-{[(1,1-dimethylethyl)oxy]carbonyl}-2-(trifluoromethyl)-L-phenylalanine;(S)-2-((tert-Butoxycarbonyl)amino)-3-(2-(trifluoromethyl)phenyl)propanoicacid;2-(Trifluoromethyl)-D-phenylalanine, N-BOC protected (Boc-D-Phe(2-CF3)-OH);
Boc-2-Trifluoromethyl-L-Phenylalanine is a Boc-protected amino acid building block derived from L-phenylalanine, featuring a 2-trifluoromethyl substituent on the aromatic ring. This non-natural, sterically and electronically modified side chain is commonly used to introduce fluorinated aromatic character into peptide and peptidomimetic frameworks, where it can influence conformational preferences and physicochemical properties relevant to medicinal chemistry lead optimization. The Boc (tert-butoxycarbonyl) group provides an established N-terminal protection state for downstream peptide assembly workflows.
1. Peptidomimetic Building Blocks
Boc-2-Trifluoromethyl-L-Phenylalanine is used by medicinal chemistry and peptide research groups to incorporate a fluorinated phenylalanine analog into peptidomimetic scaffolds and structure-activity relationship (SAR) series. The 2-trifluoromethyl substitution provides a distinct electronic and lipophilic profile compared with unsubstituted phenylalanine, making this building block a practical choice for generating analog libraries where aromatic fluorination is used to tune potency, selectivity, and metabolic behavior in preclinical optimization programs. Its Boc-protected form supports routine stepwise assembly into protected peptide intermediates used for subsequent deprotection and purification workflows.
2. Solid-Phase Peptide Synthesis
Boc-2-Trifluoromethyl-L-Phenylalanine is applied in custom peptide synthesis workflows where a protected amino acid residue is required as part of a defined sequence containing a fluorinated aromatic side chain. Peptide synthesis teams use this building block to prepare peptides that include 2-CF3-substituted phenylalanine residues for binding studies, stability comparisons, and mechanistic experiments in chemical biology. The Boc protection state enables controlled incorporation during protected-segment assembly, allowing researchers to build fluorinated peptide segments that can be carried forward into final global deprotection and characterization steps.
3. Pharmaceutical Intermediate Development
Boc-2-Trifluoromethyl-L-Phenylalanine is also used as a pharmaceutical intermediate for producing non-natural amino acid-containing fragments and advanced coupling partners in small-molecule and peptide-small-molecule conjugate development. Process and development chemists select this reagent when they need a reliably handled, N-protected fluorinated amino acid precursor to construct more complex architectures while maintaining the integrity of the CF3-substituted aromatic motif. This makes the compound a useful input for manufacturing-oriented synthesis planning, where protected amino acid residues are converted into downstream derivatives for incorporation into larger drug-like candidates and research-grade reference materials.
4. Analytical Reference Peptides
Boc-2-Trifluoromethyl-L-Phenylalanine is used to prepare defined fluorinated peptide standards and internal reference materials for analytical method development and characterization workflows. Analytical chemistry teams synthesize peptides containing the 2-trifluoromethyl phenylalanine residue to support LC-MS method qualification, peptide mapping, and comparative profiling of fluorinated analogs across synthesis batches. Because the CF3-substituted aromatic side chain provides a strong mass and structural signature, peptides built from this building block are valuable for unambiguous identification and for establishing consistent analytical behavior across related compounds.
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