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Bulk Order Boc-L-2-Iodophenylalanine丨CAS 273221-78-6
Boc-L-2-Iodophenylalanine is a protected, halogenated derivative of L-phenylalanine used in peptide synthesis and specialized organic chemistry. It contains a tert-butoxycarbonyl (Boc) protecting group on the amino functionality and an iodine substituent at the ortho position of the aromatic ring. The Boc group helps control amino-group reactivity during multistep synthesis, while the aryl iodine provides a versatile site for further chemical modification. With its defined L-configuration and distinctive substitution pattern, this compound is a useful building block for modified amino acids, peptide intermediates, and functionalized research molecules.
Chemical Identifiers
| InChI | InChI=1S/C14H18INO4/c1-14(2,3)20-13(19)16-11(12(17)18)8-9-6-4-5-7-10(9)15/h4-7,11H,8H2,1-3H3,(H,16,19)(H,17,18)/t11-/m0/s1 |
| InChI Key | CAPUJMUOMAUNOD-NSHDSACASA-N |
| Smiles | CC(C)(C)OC(=O)N[C@@H](CC1=CC=CC=C1I)C(=O)O |
| EC No. | |
| MDL No. | MFCD01860645 |
| PubChem CID | 54759073 |
Applications
Applications in Peptide Synthesis
Boc-L-2-Iodophenylalanine can be used as a building block in peptide synthesis strategies that employ Boc-protected amino acids. The Boc group can be removed under suitable acidic conditions to expose the amino group for subsequent coupling, supporting controlled assembly of peptide sequences. Its L-configuration is relevant to the preparation of stereochemically defined peptides, while the ortho-iodinated aromatic side chain offers additional opportunities for structural modification in peptide and amino acid research.
Applications in Medicinal Chemistry Research
Boc-L-2-Iodophenylalanine supports medicinal chemistry research involving modified amino acids, peptide analogues, and functionalized molecular libraries. The iodine substituent provides a useful starting point for further derivatization, while the protected amino group facilitates its incorporation into multistep synthetic routes. Researchers can use this building block to explore how aromatic substitution patterns affect molecular structure and biological interactions in target compounds.
Applications in Functionalized Amino Acid Development
This compound may be used in the preparation of specialized amino acid derivatives and other research intermediates. Its Boc protecting group supports selective manipulation of the amino functionality, and the aromatic iodine offers a potential site for additional chemical transformations. Depending on the target structure and reaction strategy, Boc-L-2-Iodophenylalanine can contribute to the development of modified amino acids, peptide building blocks, and compounds for synthetic research.
Applications in Cross-Coupling Chemistry
The aryl carbon–iodine bond can participate in compatible cross-coupling reactions, including palladium-catalyzed transformations. These reactions may allow researchers to introduce additional substituents at the ortho position and prepare structurally diverse phenylalanine derivatives. Because the iodine substituent is positioned close to the amino acid side-chain attachment point on the aromatic ring, its steric environment may influence reaction behavior and the properties of the resulting compounds.
