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Quality Product (S)-N-Boc-3-Bromophenylalanine丨CAS 82278-73-7
(S)-N-Boc-3-Bromophenylalanine is a protected derivative of a brominated phenylalanine, featuring an N-tert-butoxycarbonyl (Boc) protecting group, an S-configured chiral center, and a bromine substituent at the 3-position of the aromatic ring. The Boc group helps protect the amino functionality during multistep synthesis, while the aryl bromide provides a potential site for further functionalization. These features make the compound a valuable intermediate for peptide chemistry, medicinal chemistry, and specialized organic synthesis.
Chemical Identifiers
| InChI | InChI=1S/C14H18BrNO4/c1-14(2,3)20-13(19)16-11(12(17)18)8-9-5-4-6-10(15)7-9/h4-7,11H,8H2,1-3H3,(H,16,19)(H,17,18)/t11-/m0/s1 |
| InChI Key | FBUDYESOPLBQIR-NSHDSACASA-N |
| Smiles | CC(C)(C)OC(=O)N[C@@H](CC1=CC(=CC=C1)Br)C(=O)O |
| EC No. | 807-895-4 |
| MDL No. | MFCD01317704 |
| PubChem CID | 2734476 |
Applications
Applications in Peptide Synthesis
(S)-N-Boc-3-Bromophenylalanine can be used as a protected amino acid building block in peptide synthesis and related research. The Boc group helps limit unwanted reactions at the amino group during selected synthetic steps, while the defined stereochemistry supports the preparation of structurally specified peptide sequences and amino-acid-containing compounds.
Applications in Medicinal Chemistry
In medicinal chemistry, this compound can serve as an intermediate for preparing structurally diverse amino-acid derivatives and candidate molecules for research. The brominated aromatic ring offers a potential point for further chemical modification, enabling the exploration of molecular analogues and structure–activity relationships. Its suitability depends on the intended molecular target and synthetic route.
Applications in Cross-Coupling Reactions
Applications in Chiral Building Block Development
The S-configured stereocenter makes (S)-N-Boc-3-Bromophenylalanine relevant to the synthesis of stereochemically defined compounds. It can support multistep synthesis projects where control of amino acid configuration is important, including the preparation of specialized intermediates for pharmaceutical research and other fine chemical applications.
