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Bulk Supplier Boc-4-Bromo-L-beta-phenylalanine丨CAS 261380-20-5
Boc-4-Bromo-L-beta-phenylalanine is a protected beta-amino acid derivative featuring a tert-butoxycarbonyl (Boc) protecting group and a bromine substituent on the aromatic ring. Unlike conventional alpha-amino acids such as phenylalanine, beta-phenylalanine derivatives have a different arrangement of the amino and carboxyl functionalities, offering additional structural diversity for molecular design. The combination of Boc protection and aromatic bromination makes this compound a potential building block for specialty organic synthesis, peptide research, and medicinal chemistry.
Chemical Identifiers
| InChI | InChI=1S/C14H18BrNO4/c1-14(2,3)20-13(19)16-11(8-12(17)18)9-4-6-10(15)7-5-9/h4-7,11H,8H2,1-3H3,(H,16,19)(H,17,18)/t11-/m1/s1 |
| InChI Key | ZAMLGGRVTAXBHI-LLVKDONJSA-N |
| Smiles | CC(C)(C)OC(=O)N[C@H](CC(=O)O)C1=CC=C(C=C1)Br |
| EC No. | |
| MDL No. | MFCD01320860 |
| PubChem CID | 7009110 |
Applications
Applications in Peptide Synthesis
Boc-4-Bromo-L-beta-phenylalanine may be used as a protected building block in the preparation of beta-peptides and other beta-amino-acid-containing structures. The Boc group temporarily protects the amino functionality during selected synthetic steps, while the beta-amino acid backbone provides structural variation compared with conventional alpha-peptides. Its suitability depends on the coupling method, protecting-group strategy, and requirements of the target sequence.
Applications in Medicinal Chemistry
In medicinal chemistry, this compound can support the synthesis of structurally diverse amino-acid-derived molecules and research intermediates. The beta-amino acid framework may help researchers explore changes in molecular conformation and backbone geometry, while the brominated aromatic ring provides an opportunity for further functionalization. These characteristics may be useful in analogue development and structure–activity relationship studies.
Applications in Cross-Coupling Reactions
Applications in Chiral Building Block Development
Boc-4-Bromo-L-beta-phenylalanine is relevant to synthesis projects requiring a protected beta-amino acid with a functionalized aromatic side chain. The Boc group can be removed under suitable acidic conditions to expose the amino functionality for subsequent reactions, while the bromine substituent provides a potential handle for additional molecular modification. This combination offers flexibility in the design of multistep synthetic routes.
