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High Quality Boc-L-2,4-Dichlorophenylalanine丨CAS 114873-04-0
Boc-L-2,4-Dichlorophenylalanine is a protected non-natural amino acid used as a building block in peptide synthesis, medicinal chemistry, and organic synthesis. It contains an L-configured phenylalanine backbone with chlorine substituents at the 2- and 4-positions of the aromatic ring, while the tert-butoxycarbonyl (Boc) group protects the amino functionality during synthesis. This combination of stereochemical definition, aromatic halogen substitution, and amino protection makes the compound useful for constructing specialized peptides and complex molecules through controlled synthetic routes.
Chemical Identifiers
| InChI | InChI=1S/C14H17Cl2NO4/c1-14(2,3)21-13(20)17-11(12(18)19)6-8-4-5-9(15)7-10(8)16/h4-5,7,11H,6H2,1-3H3,(H,17,20)(H,18,19)/t11-/m0/s1 |
| InChI Key | KSDWBXFRQWMWHO-NSHDSACASA-N |
| Smiles | CC(C)(C)OC(=O)N[C@@H](CC1=C(C=C(C=C1)Cl)Cl)C(=O)O |
| EC No. | |
| MDL No. | MFCD01862942 |
| PubChem CID | 2734683 |
Applications
Applications in Peptide Synthesis
Boc-L-2,4-Dichlorophenylalanine can be used as a protected amino acid building block in the preparation of peptides and peptide analogues. The Boc group helps prevent unwanted reactions at the amino group during peptide-chain assembly and can be removed under suitable acidic conditions when required by the synthetic strategy. Its L-configuration and dichlorinated aromatic side chain allow researchers to introduce specific structural features into peptide sequences for further investigation.
Pharmaceutical and Medicinal Chemistry Research
In medicinal chemistry, Boc-L-2,4-Dichlorophenylalanine can serve as a synthetic intermediate for preparing candidate compounds containing non-natural amino acid residues. The dichlorinated phenyl group offers a defined aromatic substitution pattern for exploring structure–activity relationships and studying how halogen substitution affects molecular properties. Its protected amino functionality also supports multistep synthesis by allowing selective transformations before deprotection or subsequent coupling.
Applications in Organic Synthesis
Applications in Non-Natural Amino Acid Research
Boc-L-2,4-Dichlorophenylalanine is relevant to research involving modified amino acids and structurally diverse peptide building blocks. Its defined L-stereochemistry and protected amino group help researchers plan synthesis sequences with greater control over reaction selectivity. It may be incorporated into specialized amino acid libraries or used to prepare derivatives for studies of molecular structure, peptide conformation, and biological interactions.
