Boc-4-Trifluoromethyl-L-Phenylalanine is a Boc-protected, L-configured phenylalanine derivative bearing a 4-trifluoromethyl substituent on the aromatic side chain, classifying it as a modified proteinogenic amino acid building block for peptide chemistry. The molecule contains the Boc-protected α-amino group and a free carboxylic acid, while the para-CF3 group increases the electron-withdrawing character of the benzyl side chain and can influence conformational preferences and hydrophobic interactions in peptide contexts. In synthesis, this protected amino acid is used as a precursor for stepwise assembly of peptides and peptide analogues where the Boc group supports chemoselective handling of the α-amino functionality and the CF3-bearing aromatic side chain provides a defined structural element for structure-activity studies and chemical biology labeling designs.
CAT No: CP16804
CAS No:114873-07-3
Synonyms/Alias:114873-07-3;Boc-Phe(4-CF3)-OH;Boc-L-4-Trifluoromethylphenylalanine;(S)-2-((tert-Butoxycarbonyl)amino)-3-(4-(trifluoromethyl)phenyl)propanoicacid;Boc-4-(trifluoromethyl)-L-phenylalanine;N-BOC-4-(Trifluoromethyl)-L-phenylalanine;BOC-L-4-TRIFLUOROMETHYLPHE;Boc-4-Trifluoromethyl-L-Phenylalanine;n-boc-4-trifluoromethyl-l-phenylalanine;ST51041424;(2S)-2-[(tert-butoxycarbonyl)amino]-3-[4-(trifluoromethyl)phenyl]propanoicacid;(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[4-(trifluoromethyl)phenyl]propanoicacid;Boc-L-phe(4-CF3)-OH;AC1ODUFS;15017_ALDRICH;SCHEMBL441305;15017_FLUKA;CTK4A8951;MolPort-000-151-712;SMVCCWNHCHCWAZ-NSHDSACASA-N;167496-29-9;ZINC2569247;ANW-61835;AKOS015836550;AB07089
Boc-4-Trifluoromethyl-L-Phenylalanine is a Boc-protected L-phenylalanine derivative bearing a 4-trifluoromethyl substituent on the aromatic ring. The protected alpha-amino group makes it a practical building block for peptide and peptidomimetic assembly, while the electron-withdrawing CF3 side-chain strongly influences aromatic hydrophobicity and conformational/interaction preferences in downstream structures. This reagent is commonly selected when a CF3-bearing phenylalanine residue is needed as a defined, stereochemically consistent component in medicinal chemistry and structure-activity relationship studies.
1. Peptide Building Block
Boc-4-Trifluoromethyl-L-Phenylalanine is used as a protected amino acid building block for custom peptide synthesis workflows where a CF3-substituted phenylalanine residue must be incorporated with controlled stereochemistry. Peptide chemists typically rely on Boc-protected amino acids to prepare well-defined peptide segments and analogs for SAR campaigns, especially when the aromatic ring substitution is critical to tuning hydrophobic contacts and overall physicochemical character. The Boc protection supports downstream coupling strategies in peptide assembly, enabling consistent incorporation of the 4-CF3 phenylalanine motif into short peptides, constrained analogs, and reference standards for purification and characterization.
2. Peptidomimetic And SAR Analogues
Boc-4-Trifluoromethyl-L-Phenylalanine is frequently selected in medicinal chemistry programs that generate peptidomimetic or peptide-like analog libraries to probe how aromatic CF3 substitution affects structure-property relationships. Research groups use this building block to introduce a metabolically and electronically distinctive aryl group into lead optimization series, supporting systematic comparison of analogs where the only variable is the aromatic substitution pattern. In these workflows, the defined Boc-protected amino acid form helps ensure that the CF3-bearing residue is introduced reproducibly into analogs intended for biological screening support, hit-to-lead refinement, and analytical method development for purified compounds.
3. Pharmaceutical Intermediate Synthesis
Boc-4-Trifluoromethyl-L-Phenylalanine serves as a practical intermediate for preparing CF3-substituted phenylalanine-derived fragments used in downstream medicinal chemistry synthesis. Process development and specialty synthesis teams use this type of protected amino acid to access defined aryl-substituted amino acid motifs that can be further transformed into activated derivatives, coupling partners, or protected segment components for larger target molecules. The combination of a stable Boc-protected amine and the 4-trifluoromethyl aromatic functionality makes it a convenient starting point for assembling complex intermediates where the CF3 group must be retained and precisely positioned within the final scaffold.
4. Chiral Reference And Characterization
Boc-4-Trifluoromethyl-L-Phenylalanine is also used as a well-defined chiral reference material during analytical characterization and method development for CF3-substituted amino acid derivatives. Analytical chemistry teams employ such protected, stereochemically defined building blocks to support LC method scouting, impurity profiling, and comparative characterization of peptide fragments or amino acid-derived intermediates containing the 4-CF3 phenylalanine motif. Because the reagent is structurally specific and protected, it provides a consistent benchmark for verifying identity and assessing related synthetic material in workflows that require reliable standards for purification monitoring and documentation.
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