Boc-3-Bromo-L-Phenylalanine is a Boc-protected, halogenated amino acid derivative based on L-phenylalanine, bearing a bromine substituent at the 3-position of the aromatic side chain. The molecule contains both an N-Boc carbamate protecting group on the amino functionality and an unprotected carboxylic acid, with the stereochemical configuration indicated as L at the alpha carbon and a benzyl-like aromatic side chain that provides a site for electrophilic substitution and halogen-specific reactivity. In peptide and amide synthesis workflows, the Boc protection supports controlled chemoselectivity of the amino group while the aryl bromide provides a functional handle for subsequent diversification, including incorporation into peptide intermediates followed by coupling or cross-coupling strategies for structure-activity and labeling studies.
CAT No: CP11104
CAS No:82278-73-7
Synonyms/Alias:82278-73-7;(S)-N-Boc-3-Bromophenylalanine;Boc-L-3-Bromophenylalanine;Boc-3-bromo-L-phenylalanine;BOC-PHE(3-BR)-OH;BOC-L-3-BR-PHE-OH;(S)-3-(3-Bromophenyl)-2-((tert-butoxycarbonyl)amino)propanoicacid;BOC-L-3-BROMOPHE;(2S)-3-(3-bromophenyl)-2-[(tert-butoxycarbonyl)amino]propanoicacid;SBB063976;(2S)-2-[(tert-butoxy)carbonylamino]-3-(3-bromophenyl)propanoicacid;(2S)-3-(3-BROMOPHENYL)-2-(TERT-BUTOXYCARBONYLAMINO)PROPIONICACID;BOC-3-BROMO-L-PHE-OH;AC1MC183;BOC-L-PHE(3-BR)-OH;SCHEMBL1073538;CTK8B2367;FBUDYESOPLBQIR-NSHDSACASA-N;MolPort-000-150-165;82278-95-3;ZINC2244130;ANW-37536;CB-500;KM2111;N-BOC-L-3-BROMOPHENYLALANINE
Boc-3-Bromo-L-Phenylalanine is a Boc-protected L-phenylalanine derivative bearing a bromine substituent on the aromatic ring at the 3-position. As a protected amino acid building block, it is commonly used to introduce a halogenated phenylalanine side chain into peptide sequences during protected-amino-acid assembly. The combination of the Boc N-terminus and the aryl bromide makes it useful both for constructing defined peptide intermediates and for downstream functional diversification via halogen-based chemistry.
1. Halogenated Peptide Building Block
Boc-3-Bromo-L-Phenylalanine is used by peptide synthesis groups to incorporate 3-bromophenylalanine residues into protected peptide segments for custom peptide manufacturing and structure-activity relationship (SAR) studies. The brominated aromatic side chain provides a distinct handle for maintaining site-specific chemical identity in peptide analog libraries, while the Boc protection supports standard peptide coupling workflows that rely on controlled deprotection and sequential assembly. Researchers frequently select this building block when they need a halogenated phenylalanine variant to probe how aromatic substitution patterns influence peptide conformation, binding interactions, or stability trends across analog series.
2. Medicinal Chemistry SAR Intermediates
Boc-3-Bromo-L-Phenylalanine is also used in medicinal chemistry programs to prepare halogenated amino acid intermediates that feed into peptidomimetic and small-molecule scaffolds requiring a brominated aromatic motif. The aryl bromide enables common downstream transformations used in medicinal chemistry lead optimization, allowing teams to rapidly diversify analogs from a single branching point while preserving the stereochemical identity of the L-amino acid backbone. Pharmaceutical intermediate development groups value this reagent form because it provides a protected, isolable amino acid unit that can be carried through multi-step synthesis before final coupling or elaboration.
3. Functionalization Via Aryl Bromide
Boc-3-Bromo-L-Phenylalanine supports downstream chemical functionalization strategies where the aromatic bromine acts as a reactive site for installing additional substituents on the phenyl ring after peptide or intermediate formation. Chemical biology and materials chemistry teams often use halogenated amino acid building blocks to generate defined aromatic substitution patterns that are difficult to achieve from non-halogenated precursors. In practical workflows, the Boc-protected amino acid form helps maintain compatibility with peptide/fragment assembly steps, while the retained aryl bromide provides a chemically distinct branching point for later derivatization to produce tailored analogs, conjugation-ready intermediates, or specialized structure probes.
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