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Other Specialized Reagents

(R)-N-Boc-3-Bromophenylalanine

Category:

Other Specialized Reagents

CAS NO:

261360-77-4

Standard:

BP,USP,

Price Range:

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Main Sales Markets:

North America,Western Europe,Eastern Europe

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Shanghai Sunwise Chemical Co., Ltd.

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Basic Info

CAS Number

261360-77-4

Pharmacopoeia

BP,USP

Grade

Pharmaceutical Grade

Is Manufacturer

YES

Product Description

Pharmaceutical Raw Materials and Intermediates

AI Product Description

*The following content is generated by AI and is for reference only.

(R)-N-Boc-3-Bromophenylalanine is a highly specialized chiral building block widely utilized in modern organic synthesis and pharmaceutical research. With the molecular formula C13H16BrNO4 and a CAS number of 207598-68-9, this compound serves as a protected derivative of the essential amino acid phenylalanine. The molecule features a bromine atom substituted at the meta-position of the phenyl ring, coupled with an N-tert-butoxycarbonyl (Boc) protecting group on the alpha-amino functionality. This specific structural configuration ensures high stereochemical purity, typically retaining the natural L-(R) configuration, which is critical for biological activity in drug development. The primary application of (R)-N-Boc-3-Bromophenylalanine lies in the construction of complex peptidomimetics and bioactive molecules. The presence of the aryl bromide moiety makes it an ideal substrate for transition-metal-catalyzed cross-coupling reactions, such as Suzuki-Miyaura or Heck couplings. These transformations allow chemists to attach diverse functional groups to the aromatic ring, thereby expanding the chemical space available for lead optimization in medicinal chemistry. Furthermore, the Boc group provides robust protection during peptide assembly, preventing unwanted side reactions at the amine site while allowing for selective deprotection under acidic conditions when necessary. In the pharmaceutical industry, derivatives synthesized from this precursor are often investigated for their potential therapeutic properties, including antiviral, anticancer, and anti-inflammatory activities. Its role as a versatile intermediate facilitates the rapid generation of compound libraries for high-throughput screening. Researchers value its stability and solubility characteristics, which simplify handling and purification processes in both academic laboratories and industrial settings. By enabling precise modifications to the phenylalanine scaffold, this reagent accelerates the discovery of novel pharmacophores. Overall, (R)-N-Boc-3-Bromophenylalanine stands as a fundamental tool for synthetic chemists aiming to design sophisticated small-molecule drugs with enhanced potency and selectivity, bridging the gap between simple amino acids and complex therapeutic agents.