Manufacturer: Hangzhou Royalchem Co.,LTD.
Website: www.cnroyalchem.com
【 Providing a complete set of intermediates and impurities for Lifitegrast 】
【 Providing a complete set of intermediates and impurities for Lifitegrast 】
【 Providing a complete set of intermediates and impurities for Lifitegrast 】
Product Identification & Chemical Information
Product Name: (S)-Methyl 2-amino-3-(3-bromophenyl)propanoate hydrochloride
Synonyms:
(S)-Methyl 3-(3-bromophenyl)alaninate hydrochloride
(S)-3-(3-Bromophenyl)-alanine methyl ester hydrochloride
L-m-Tyrosine(3-Br), methyl ester hydrochloride
(S)-2-Amino-3-(3-bromophenyl)propionic acid methyl ester hydrochloride
CAS Registry Number: 880347-43-3
Molecular Formula: C₁₀H₁₂BrNO₂ · HCl
Molecular Weight: 294.58 / 295.02 g/mol (monoisotopic)
Chemical Structure:
Contains a chiral α-amino acid ester backbone with an S-configuration at the alpha-carbon.
Features a 3-bromophenyl substituent on the beta-carbon.
Exists as the hydrochloride (HCl) salt form, enhancing stability and water solubility compared to the free base.
Structural Formula: [H₃N⁺-CH(CH₂-C₆H₄-3-Br)-COOCH₃] Cl⁻
Key Characteristics & Properties
Chirality: This product is the (S)-enantiomer . Enantiomeric purity is critical for applications involving chiral recognition, such as asymmetric synthesis or biological studies. Specific optical rotation values ([α]D) may be provided on the Certificate of Analysis (CoA).
Functionality: Combines an amino group (primary amine, protonated as ammonium), an ester group (methyl ester), and a brominated aromatic ring (3-bromophenyl). The hydrochloride salt neutralizes the amine.
Solubility: Generally soluble in polar solvents like water, methanol, ethanol, DMF, DMSO. Less soluble in non-polar solvents like hexane or diethyl ether. Solubility depends on concentration and temperature.
Applications & Uses
Primary Applications:
Pharmaceutical Intermediates: Crucial building block for synthesizing more complex molecules, particularly potential drug candidates or bioactive compounds. The chiral alpha-carbon and the versatile bromine handle make it valuable for structure-activity relationship (SAR) studies in medicinal chemistry.
Organic Synthesis: Used as a chiral synthon in asymmetric synthesis. The bromine atom facilitates further functionalization via cross-coupling reactions (e.g., Suzuki, Stille, Sonogashira) to introduce diverse substituents onto the aromatic ring. The amino and ester groups also offer sites for further derivatization.
Chemical Research: Valuable tool compound in academic and industrial labs for studying enzyme mechanisms (e.g., as a substrate or inhibitor analog for amino acid-metabolizing enzymes), peptide mimetics development, or material science research involving functionalized chiral molecules.
Peptidomimetics: Serves as a non-natural amino acid derivative for incorporation into peptide chains to modify stability, activity, or binding properties.
Handling, Storage & Safety
Storage Conditions: Store tightly sealed in the original container under an inert atmosphere (if provided). Keep in a cool, dry place . Recommended storage temperature is typically 2-8°C (refrigerated) for long-term stability. Protect from light, moisture, heat, and incompatible materials.
Stability: Stable under recommended storage conditions. Avoid exposure to strong oxidizing agents, strong acids, strong bases, and excessive heat. Moisture can hydrolyze the ester group over time; store desiccated.
Safety Data:
GHS Hazard Statements: (Consult specific SDS)
H315: Causes skin irritation.
H319: Causes serious eye irritation.
H335: May cause respiratory irritation.
Precautionary Statements: (Consult specific SDS).
P261: Avoid breathing dust/fume/gas/mist/vapours/spray.
P264: Wash hands thoroughly after handling.
P271: Use only outdoors or in a well-ventilated area.
P280: Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352: IF ON SKIN: Wash with plenty of water/...
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P332+P313: If skin irritation occurs: Get medical advice/attention.
P337+P313: If eye irritation persists: Get medical advice/attention.
P362+P364: Take off contaminated clothing and wash it before reuse.
P403+P233: Store in a well-ventilated place. Keep container tightly closed.
P405: Store locked up.
Handling: Handle in a well-ventilated area (e.g., fume hood) using appropriate personal protective equipment (PPE), including lab coat, nitrile or neoprene gloves, and safety goggles. Avoid contact with skin, eyes, and clothing. Avoid generating or inhaling dust. Practice good hygiene.
Disposal: Dispose of contents and container according to local, regional, national, and international regulations. Consult the Safety Data Sheet (SDS) for specific guidance. Do not dispose of into the environment. Treat as hazardous chemical waste.
