N-(tert-butyloxycarbonyl)-3-(4-iodophenyl)alanine, CAS No. 62129-44-6

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62129-44-6

Catalog No. EBD268959

CAS 62129-44-6

Name N-(tert-butyloxycarbonyl)-3-(4-iodophenyl)alanine

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Basic Information

Synonyms: boc-4-iodo-L-phenylalanine Boc-L-4-Iodophenylalanine Boc-L-Phe(4-I)-OH Boc-Phe(4-I)-OH N-(tert-butyloxycarbonyl)-3-(4-iodophenyl)alanine N-Boc-p-iodo-L-phenylalanine N-Boc-4-iodophenylalanine Boc-4-iodo-L-Phe

Molecular Formula: C14H18INO4

Molecular Weight: 391.2

MDL Number: MFCD00037119

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Drug Synthesis Building Blocks

Product Description:

N-(tert-Butyloxycarbonyl)-3-(4-iodophenyl)alanine (Boc-4-Iodo-L-Phenylalanine) is a protected amino acid derivative featuring a tert-butyloxycarbonyl (Boc) group on the amine and an iodine atom at the para position of the phenylalanine side chain. It serves as a crucial chiral building block in peptide synthesis and medicinal chemistry. Its primary application is in the synthesis of peptide-based pharmaceuticals and bioactive compounds. The iodine atom on the aromatic ring provides a versatile handle for further functionalization via cross-coupling reactions (e.g., Suzuki, Sonogashira), enabling the introduction of diverse substituents to explore structure-activity relationships. This makes it a valuable intermediate in the development of drug candidates, particularly for targeted therapies and molecular probes. As a Boc-protected derivative, it offers stability and selective deprotection under mild acidic conditions, facilitating its use in solid-phase and solution-phase peptide synthesis. It is a standard reagent for constructing modified peptides containing iodinated phenylalanine residues.

Physical Properties

Melting Point: ~150 °C (dec.)

Boiling Point: 475.3 °C at 760 mmHg

Flash Point: 241.3 °C

Density: 1.56 g/cm3

Storage: Store at 0°C

Analytical Data

Appearance: White powder