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Professional Supplier 4-Bromophenylalanine丨CAS 14091-15-7
4-Bromophenylalanine is a halogenated derivative of phenylalanine featuring a bromine substituent at the para position of the aromatic ring. This structural modification provides a useful functional handle for further chemical transformations while retaining the amino acid framework. As a specialty building block, 4-Bromophenylalanine is relevant to organic synthesis, medicinal chemistry, peptide research, and the development of functionalized amino acid derivatives.
Chemical Identifiers
| InChI | InChI=1S/C9H10BrNO2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13) |
| InChI Key | PEMUHKUIQHFMTH-UHFFFAOYSA-N |
| Smiles | C1=CC(=CC=C1CC(C(=O)O)N)Br |
| EC No. | 237-941-3 |
| MDL No. | MFCD00002599 |
| PubChem CID | 85681 |
Applications
Applications in Peptide Synthesis
As a non-standard amino acid building block, 4-Bromophenylalanine may be used in peptide research when a brominated aromatic side chain is required. Introducing this modified residue can help researchers investigate how aromatic substitution affects peptide structure, molecular interactions, and other properties. Depending on the synthesis strategy, the amino and carboxyl groups may require suitable protection or activation before incorporation into a peptide sequence.
Applications in Medicinal Chemistry
4-Bromophenylalanine can serve as an intermediate in the synthesis of amino-acid-derived compounds and structurally diverse research molecules. The bromine substituent offers opportunities for further aromatic functionalization, enabling researchers to prepare molecular analogues and explore structure–activity relationships. Its application depends on the target structure, the required stereochemistry, and the selected synthetic route.
Applications in Cross-Coupling Reactions
Applications in Chiral Building Block Development
4-Bromophenylalanine can support the preparation of specialized amino acid derivatives and other stereochemically defined molecules. Because the product's stereochemical identity is important in many pharmaceutical and peptide applications, users should confirm whether the required material is the L-isomer, D-isomer, or a racemic form before selecting a specification. This distinction helps ensure compatibility with the intended synthesis and research objectives.
