(S)-N-Boc-3-Bromophenylalanine RC00152

Manufacturer: Hangzhou Royalchem Co.,LTD.

Website:  www.cnroyalchem.com

Product Name  

(S)-N-[(tert-Butoxy)carbonyl]-3-bromo-L-phenylalanine
(Commonly abbreviated as: (S)-N-Boc-3-Bromophenylalanine, Boc-3-Br-Phe-OH)

CAS Number

82278-73-7

Molecular Formula

C₁₄H₁₈BrNO₄

Molecular Weight

344.20 g/mol

Solubility:  Soluble in organic solvents such as dimethylformamide (DMF), dimethyl sulfoxide (DMSO), dichloromethane (DCM), and tetrahydrofuran (THF). Sparingly soluble or insoluble in water.

Storage Conditions:  Store at  -20°C  under inert atmosphere (e.g., argon or nitrogen) to minimize degradation and racemization. Protect from light and moisture.

Key Features

Chiral Building Block:  An enantiomerically pure  L -phenylalanine derivative bearing a  meta -bromine substituent on the aromatic ring and protected at the α-amino group with a  tert -butoxycarbonyl (Boc) group.

Protected Amino Acid:  The Boc group provides orthogonal protection for the α-amino group, allowing selective deprotection under mild acidic conditions (e.g., TFA or HCl) without affecting the carboxylic acid or the bromine substituent.

Reactive Handle:  The bromine atom at the  meta  position of the phenyl ring is a versatile site for further synthetic elaboration via cross-coupling reactions (e.g., Suzuki, Stille, Sonogashira, Heck) or nucleophilic substitution, enabling the introduction of diverse substituents onto the aromatic core.

Peptide Synthesis:  Primarily used in solid-phase peptide synthesis (SPPS) and solution-phase peptide synthesis to incorporate a modified phenylalanine residue with a functionalizable bromine handle at the  meta -position into peptide sequences.

Pharmaceutical Intermediates:  A valuable intermediate in the synthesis of complex molecules, bioactive peptides, peptidomimetics, and drug candidates, especially those requiring modified aromatic amino acids for structure-activity relationship (SAR) studies or targeted delivery.

Applications

Peptide Chemistry:  Incorporation into peptides during Boc-SPPS or solution-phase synthesis.

Medicinal Chemistry:  Synthesis of constrained peptides, peptidomimetics, and non-natural amino acid derivatives for drug discovery.

Chemical Biology:  Tool for attaching labels, fluorophores, or other functional groups via the bromine atom within a peptide context.

Material Science:  Building block for functionalized polymers or novel biomaterials.

Organic Synthesis:  Intermediate for the synthesis of complex organic molecules, heterocycles, or catalysts featuring a chiral bromoarylalanine moiety.

Quality Control

Identity confirmed by  ¹H NMR ,  ¹³C NMR , and  FT-IR  spectroscopy.

Purity determined by  Reverse-Phase HPLC  (UV detection).

Enantiomeric excess (ee) determined by  Chiral HPLC .

Consistent melting point range.

Trace metal analysis available upon request.

Handling & Safety

Safety Data Sheet (SDS):  Available upon request. Must be consulted prior to use.

Hazard Statements:  May be harmful if swallowed, in contact with skin, or if inhaled. Causes skin and eye irritation. May cause respiratory irritation.

Precautionary Measures:  Handle in a well-ventilated fume hood. Wear appropriate personal protective equipment (PPE) including safety glasses, gloves (nitrile recommended), and lab coat. Avoid contact with skin, eyes, and clothing. Avoid dust formation.

Disposal:  Dispose of in accordance with local, regional, national, and international regulations. Treat as hazardous chemical waste.