4-Bromo-DL-Phenylalanine contains a phenylalanine backbone bearing a bromine substituent at the para (4-) position of the aromatic side chain, classifying it as a halogenated, non-proteinogenic/derivatized phenylalanine analogue used in peptide and labeling chemistry. The molecule presents an amino functional group and a carboxyl functional group on the α-carbon, and the "DL" designation indicates a racemic mixture of stereoisomers at that center, which can affect incorporation outcomes in structure-activity and stereochemical studies. Its aryl bromide provides a chemically addressable handle for cross-coupling or other derivatization strategies, and it is employed as a substrate analogue in peptide synthesis workflows and as a building block for preparing halogenated amino acid and peptide derivatives for chemical biology and analytical method development.
CAT No: CP11203
CAS No:14091-15-7
Synonyms/Alias:p-Bromo-DL-phenylalanine;2-amino-3-(4-bromophenyl)propanoicacid;14091-15-7;4-Bromo-dl-phenylalanine;4-Bromo-phenylalanine;4-Bromophenylalanine;DL-4-Br-Phe-OH;H-DL-PHE(4-BR)-OH;PEMUHKUIQHFMTH-UHFFFAOYSA-N;NSC-12762;2-Amino-3-(4-bromophenyl)propionicacid;ST044496;2-AMINO-3-(4-BROMO-PHENYL)-PROPIONICACID;Phenylalanine,4-bromo-;p-Br-Phenylalanine;1991-80-6;p-Br-Phe;para-Bromophenylalanine;4-Bromophenylalanine#;dl-4-Bromophenylalanine;ACMC-1CQRQ;ACMC-209ga6;AC1L39ZB;DL-PHE(4-BR)-OH;DL-Phenylalanine,4-bromo-
4-Bromo-DL-Phenylalanine is a halogenated phenylalanine derivative supplied as a DL mixture, providing both stereochemical forms for synthetic and analytical workflows where racemic material is acceptable. The side chain retains the amino acid backbone functionality while the para-bromo substituent on the aromatic ring offers a chemically distinct handle for downstream derivatization, including cross-coupling and aromatic functional group transformations. This product is commonly used as a building block in medicinal chemistry and peptide-related intermediate development where aryl halides are required to access substituted aromatic motifs.
1. Medicinal Chemistry Intermediates
4-Bromo-DL-Phenylalanine is widely used in medicinal chemistry programs as an aryl bromide-containing amino acid building block for preparing substituted aromatic analogs. Researchers incorporate the amino acid framework into peptidomimetic scaffolds and side-chain-modified intermediates where the para-bromo group enables efficient diversification via palladium-catalyzed cross-coupling strategies. The availability as a DL mixture supports parallel synthesis and SAR exploration when stereochemical resolution is deferred to later stages or when racemic analogs are acceptable for early discovery libraries.
2. Peptidomimetic And Analog Synthesis
4-Bromo-DL-Phenylalanine serves as a practical precursor for constructing peptidomimetic and amino acid-derived analogs that retain an aromatic side chain while introducing a site for late-stage functionalization. Chemical biology and medicinal chemistry groups use this reagent to generate series of substituted phenylalanine derivatives for structure-activity relationship studies, where the para-bromo substituent provides a direct entry point to introduce alternative aryl groups or heteroaryl substituents. The amino acid backbone also supports downstream conversion into protected or activated forms during custom intermediate assembly for analog manufacturing.
3. Aromatic Diversification By Coupling
4-Bromo-DL-Phenylalanine is selected for workflows that require an aryl bromide as a robust synthetic "handle" on an amino acid scaffold. Synthetic chemists use the para-bromo functionality to access substituted aromatic products through standard coupling and aryl exchange approaches, enabling rapid generation of analog diversity without redesigning the core amino acid skeleton. This makes the compound useful in intermediate libraries for process development and scale-up planning, particularly when the amino acid stereochemistry is not the primary variable at the stage of aromatic diversification.
4. Analytical Reference Material Development
4-Bromo-DL-Phenylalanine is also used in analytical method development and reference standard preparation for LC-MS and related characterization workflows involving halogenated amino acid derivatives. Laboratories preparing calibration or qualitative identification standards for substituted phenylalanine species rely on the defined aryl bromide substitution to match expected mass and fragmentation behavior. The DL form is advantageous when the analytical goal is to track the presence of the brominated phenylalanine motif irrespective of stereochemical assignment, such as during early-stage synthesis monitoring or intermediate profiling.
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