Description

Boc-(S)-α-(4-Bromobenzyl)-Proline is a high-purity, non-natural amino acid derivative featuring a tert-butoxycarbonyl (Boc) protecting group and a chiral (S)-proline core substituted with a 4-bromobenzyl moiety. This compound is a critical chiral building block and intermediate in modern organic synthesis, particularly valued for its role in constructing complex, biologically active molecules. It is primarily utilized by research institutions and pharmaceutical companies engaged in the development of peptide-based therapeutics, protease inhibitors, and other drug discovery programs where precise stereochemistry and functional group manipulation are paramount.

Application

• Pharmaceutical Intermediate: A key chiral synthon in the research and development of novel Active Pharmaceutical Ingredients (APIs), especially for protease inhibitors and peptide drugs.
• Peptide Synthesis: Used in solid-phase and solution-phase peptide synthesis (SPPS) to incorporate a constrained proline derivative with a hydrophobic, halogenated side chain, influencing peptide conformation and bioactivity.
• Medicinal Chemistry: Serves as a versatile building block for structure-activity relationship (SAR) studies and the creation of focused compound libraries targeting various disease pathways.
• Chemical Biology Probes: Employed in the synthesis of labeled or modified peptides used as probes to study enzyme mechanisms, protein-protein interactions, and cellular processes.
• Asymmetric Synthesis: Acts as a chiral auxiliary or precursor in catalytic asymmetric reactions to induce stereoselectivity in the synthesis of complex organic molecules.
• Contract Research & Manufacturing (CRAM): Supplied to CROs and CDMOs for custom synthesis projects requiring high-fidelity chiral intermediates.

Basic Information

Product Name	Boc-(S)-α-(4-Bromobenzyl)-Proline
CAS No.	706806-77-1
Molecular Formula	C₁₇H₂₂BrNO₄
Molecular Weight	384.27 g/mol
Synonyms	(2S)-1-[(2-Methylpropan-2-yl)oxycarbonyl]-2-[(4-bromophenyl)methyl]pyrrolidine-2-carboxylic acid; (S)-1-Boc-2-(4-bromobenzyl)proline; Boc-S-4-Br-Bn-Pro-OH; 1-Boc-2-(4-bromobenzyl)-(S)-proline; tert-Butyl (2S)-2-[(4-bromophenyl)methyl]-2-carboxypyrrolidine-1-carboxylate; N-Boc-2-(4-bromobenzyl)-(S)-proline; (S)-1-(tert-Butoxycarbonyl)-2-(4-bromobenzyl)pyrrolidine-2-carboxylic acid
EINECS	Contact for details

Quality Control

Our Boc-(S)-α-(4-Bromobenzyl)-Proline is manufactured under strict quality management systems. Each batch undergoes rigorous analytical testing to ensure high chemical purity, correct stereochemistry, and consistent performance. Standard quality parameters include assay by HPLC, chiral purity determination, and control of specified impurities. A comprehensive Certificate of Analysis (COA) detailing all test results is provided with every shipment to support your quality assurance and regulatory documentation needs.

Storage

Preserve in a tightly closed container, protected from light. Store in a cool, dry place at a controlled room temperature (15-25°C). This material is hygroscopic (moisture-sensitive) and should be handled in a dry environment to prevent degradation. For long-term storage, consider storing under an inert atmosphere.

Specification

Item	Specification
Appearance	White to off-white crystalline powder
Identification (IR)	Conforms to structure
Assay (HPLC)	≥ 98.0%
Chiral Purity (HPLC)	≥ 99.0% ee
Water Content (KF)	≤ 0.5%
Residue on Ignition	≤ 0.1%
Heavy Metals	≤ 10 ppm

Note: Specifications can be tailored. Please contact us for the detailed technical data sheet of a specific grade.