Understanding the intricate chemical properties of specialized reagents is fundamental for successful synthetic chemistry. NINGBO INNO PHARMCHEM CO.,LTD. focuses on providing compounds with well-defined characteristics, such as Boc-2-bromo-L-phenylalanine (CAS 261165-02-0), a compound vital for peptide synthesis and organic chemistry.

Boc-2-bromo-L-phenylalanine is characterized by its specific molecular structure, which includes a phenylalanine backbone, a tert-butyloxycarbonyl (BOC) group protecting the amine, and a bromine atom substituted at the ortho position (2-position) of the phenyl ring. This structure dictates its chemical behavior and utility. The BOC group is a common and effective protecting group for amines. It is stable under a variety of reaction conditions, including many nucleophilic and basic conditions, but can be readily removed under mild acidic conditions, such as treatment with trifluoroacetic acid (TFA). This selective deprotection is essential for stepwise peptide synthesis, allowing sequential coupling of amino acids.

The presence of the bromine atom is a key feature that enhances the synthetic utility of Boc-2-bromo-L-phenylalanine. Bromine is an excellent leaving group and a versatile functional handle in organic synthesis. It readily participates in various metal-catalyzed cross-coupling reactions, such as Suzuki-Miyaura, Heck, Sonogashira, and Buchwald-Hartwig amination reactions. These reactions enable the facile introduction of diverse carbon-based or nitrogen-based substituents onto the aromatic ring, opening pathways to create highly functionalized molecules. For example, a researcher might buy Boc-2-bromo-L-phenylalanine specifically for its potential to undergo a Suzuki coupling to introduce a new aromatic moiety, thereby altering the electronic or steric properties of the final peptide or molecule.

Chemically, Boc-2-bromo-L-phenylalanine is typically a crystalline solid, often appearing as a white to off-white powder. Its solubility is generally good in common organic solvents like dichloromethane, ethyl acetate, and methanol, while its solubility in water is limited due to the hydrophobic nature of the bromophenyl group and the tert-butyl ester. The chirality of the compound, being derived from L-phenylalanine, is also a critical aspect, particularly for applications in biologically relevant molecules where stereochemistry dictates function.

The overall chemical properties of Boc-2-bromo-L-phenylalanine make it an attractive building block for synthesizing complex peptides, peptidomimetics, and small molecule drugs. Its predictable reactivity and the ease of manipulating the bromine substituent contribute significantly to its value in research and development. For any synthetic chemist, having access to reliable information about the chemical properties of Boc-2-bromo-L-phenylalanine and sourcing it from reputable suppliers like NINGBO INNO PHARMCHEM CO.,LTD. is paramount for achieving successful experimental outcomes.