In the realm of specialized organic chemistry, understanding the precise chemical properties and applications of key reagents is vital for successful synthesis and product development. Boc-L-4-Bromophenylalanine (CAS 62129-39-9) is one such compound, widely utilized in peptide synthesis and as a crucial pharmaceutical intermediate. This article delves into its defining characteristics and the impact it has across various research and industrial applications.

Boc-L-4-Bromophenylalanine is a protected derivative of the amino acid phenylalanine. Its molecular formula is C14H18BrNO4, with a molecular weight of 344.2 g/mol. Physically, it typically appears as an off-white to white powder. The defining features of this molecule are the tert-butoxycarbonyl (Boc) group, attached to the alpha-amino nitrogen, and the bromine atom substituent at the para-position of the phenyl ring. The Boc group is a base-labile protecting group commonly employed in peptide chemistry. It shields the amino terminus from unwanted reactions during peptide bond formation, ensuring that coupling reactions occur specifically between the carboxyl group of one amino acid and the amino group of the next. Its removal is typically achieved using mild acidic conditions, such as trifluoroacetic acid (TFA).

The bromine atom on the aromatic ring introduces significant synthetic versatility. This halogen can participate in a variety of palladium-catalyzed cross-coupling reactions, including Suzuki-Miyaura, Heck, and Sonogashira couplings, as well as Buchwald-Hartwig aminations. These reactions allow for the introduction of a wide array of functional groups or larger molecular fragments onto the phenylalanine side chain, enabling the synthesis of complex peptidomimetics, labeled peptides, or drug conjugates. This makes Boc-L-4-Bromophenylalanine an indispensable building block for chemists aiming to create sophisticated molecular architectures.

In terms of solubility, Boc-L-4-Bromophenylalanine is generally soluble in common organic solvents such as chloroform, dichloromethane, ethyl acetate, and DMSO, facilitating its use in solution-phase and solid-phase synthesis protocols. Its stability under typical laboratory conditions, when stored properly (e.g., in a cool, dry place, sealed), ensures its utility for extended research projects.

The primary applications of Boc-L-4-Bromophenylalanine lie in two main areas: first, as a critical reagent in peptide synthesis, particularly for introducing modified or functionalized phenylalanine residues into peptide sequences. Second, it serves as a valuable pharmaceutical intermediate in the synthesis of various active pharmaceutical ingredients (APIs). Its ability to be further functionalized makes it a versatile starting material for developing new drug candidates with tailored properties. For researchers and manufacturers looking to purchase this compound, partnering with a reliable supplier that emphasizes high purity (e.g., ≥98% HPLC) and consistent quality is essential. Sourcing from experienced manufacturers, such as those in China, can provide access to competitively priced materials with guaranteed quality, supporting both R&D and large-scale production needs.