2-Bromo-DL-Phenylalanine is a halogenated phenylalanine derivative featuring a benzyl side chain bearing a bromo substituent at the 2-position relative to the alpha carbon, with an amino group and a carboxyl group on the alpha backbone. The "DL" designation indicates a racemic mixture of stereoisomers, and the molecule retains the characteristic amino acid functionality while the bromine substituent provides a chemically addressable handle for further derivatization. In synthetic and chemical biology workflows, this compound is used as a substrate for preparing modified amino acid building blocks and for incorporating a halogenated aromatic residue into peptide analogues or labeling strategies that require a reactive bromo-functional group.
CAT No: CP11003
CAS No:30163-16-7
Synonyms/Alias:2-amino-3-(2-bromophenyl)propanoicacid;2-Bromo-DL-Phenylalanine;2-Bromophenylalanine;dl-2-Bromophenylalanine;1991-79-3;30163-16-7;DL-2-BR-PHE-OH;(R)-2-BromophenylalanineHydrochloride;2-Bromophenylalanine#;AC1LBA4A;SCHEMBL43301;AC1Q26E4;2-BROMOPHENYL-DL-ALANINE;CTK8C3111;JFVLNTLXEZDFHW-UHFFFAOYSA-N;MolPort-003-990-077;0240AB;ANW-69690;AR-1D9733;AKOS000168432;AKOS016843139;AB21653;AM82701;VC30987;AK-80271
2-Bromo-DL-Phenylalanine is a halogenated phenylalanine building block supplied as a DL mixture, providing both stereochemical forms for synthetic flexibility in downstream derivatization. The side-chain benzyl ring bears a bromine substituent, making this reagent a practical electrophile handle for C-C and C-heteroatom bond-forming transformations and for preparing halogenated analogs used in medicinal chemistry and chemical biology workflows. As an amino acid scaffold, it also supports incorporation into protected-peptide or peptide-analog synthesis strategies where a brominated aromatic motif is required.
1. Medicinal Chemistry Analog Synthesis
2-Bromo-DL-Phenylalanine is commonly used in medicinal chemistry programs to construct brominated aromatic analogs and peptidomimetic scaffolds where a halogenated phenylalanine motif is required for SAR (structure-activity relationship) studies. Medicinal chemistry teams leverage the bromine substituent as a synthetic handle to access further functionalization routes, enabling rapid diversification of aromatic substitution patterns during lead optimization. The DL stereochemical supply supports parallel synthesis and screening workflows where stereochemical resolution may be deferred until later stages, such as when downstream assays or binding studies indicate a preferred configuration.
2. Halogen-Directed Cross-Coupling Building Block
2-Bromo-DL-Phenylalanine serves as a direct starting material for preparing bromine-functionalized intermediates that feed into palladium-catalyzed cross-coupling chemistry and other halogen-directed coupling strategies. Synthetic chemistry groups use the brominated aromatic ring to introduce new substituents onto the phenyl ring, generating analogs with altered electronics, sterics, and physicochemical properties while retaining the amino acid core for further conversion into protected derivatives or coupling-ready forms. This makes the reagent valuable for building libraries of substituted phenylalanine derivatives used in discovery chemistry, chemical biology probe development, and material precursor synthesis where aromatic substitution control is important.
3. Peptide-Analog and Protected Intermediate Development
2-Bromo-DL-Phenylalanine is also used as an amino acid precursor for peptide-analog synthesis and for preparing brominated protected amino acid derivatives that can be assembled into longer sequences. Research groups developing non-natural peptide structures, enzyme-substrate mimics, or structure-defined peptidomimetics rely on the amino acid scaffold to maintain backbone recognition motifs while introducing a brominated aromatic side chain for downstream derivatization or for tuning properties of the final construct. In practical workflows, the DL mixture supports efficient early-stage synthesis of mixed-stereochemistry libraries, with stereochemical refinement handled separately if required by the specific biological or analytical application.
4. Chemical Biology Probe and Label Precursor
2-Bromo-DL-Phenylalanine is frequently selected as a precursor for chemical biology probes and labeling reagents that require a brominated aromatic motif as a synthetic "attachment point" for later functionalization. Chemical biology teams use the amino acid framework to generate probe scaffolds that can be elaborated into more complex structures, including aromatic variants used for binding studies, affinity reagents, or substrate analogs in biochemical assays. The bromine substituent provides a convenient handle for subsequent derivatization steps, allowing probe libraries to be generated with controlled aromatic substitution while maintaining the amino acid-based architecture needed for consistent scaffold assembly.
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