L-Phenylalaninamide Hydrochloride, with the CAS number 65864-22-4, is a chiral amino acid amide hydrochloride derivative, also known as (S)-2-Amino-3-phenylpropanamide hydrochloride. Its molecular formula is C₉H₁₃ClN₂O, and its molecular weight is 200.67 g/mol. It features the L-configuration of phenylalanine, with an amide group replacing the carboxyl group of the parent amino acid and a hydrochloride salt form, combining high water solubility, good chemical stability, and specific chiral reactivity, making it widely applied in pharmaceutical synthesis, peptide chemistry, and biochemistry research.
Physically, it appears as a white to off-white crystalline powder or granular solid. It has a melting point of approximately 220-225℃ (decomposition) and is highly soluble in water and polar organic solvents such as methanol and ethanol, while slightly soluble in dimethylformamide and insoluble in non-polar solvents. It is optically active, with a specific rotation [α]²⁰/D of +28.0° to +32.0° (in water, c=1), reflecting its L-configuration. It has low hygroscopicity and remains stable under normal temperature and pressure when stored properly, facilitating easy handling, storage, and formulation in various chemical and biological processes.
Chemically, its core chiral center, phenyl group, amide group, and hydrochloride moiety are key to its properties. The L-configuration ensures high stereoselectivity, which is critical for its application in chiral synthesis and pharmaceutical development. The hydrochloride salt form significantly enhances its water solubility and chemical reactivity compared to the free amide form. It is stable under neutral and weakly acidic conditions but may undergo hydrolysis under strong alkali or high-temperature environments, and can participate in amidation, condensation, and substitution reactions, making it an ideal chiral building block for organic synthesis.
Its core applications focus on pharmaceutical synthesis and peptide chemistry. As a key intermediate, it is widely used in the synthesis of peptide drugs, chiral pharmaceuticals, and antidepressant agents, particularly compounds targeting neurological disorders and metabolic diseases. Its amide structure is easily modified to form peptide bonds, making it a valuable tool in the assembly of complex peptide chains. Additionally, it serves as a biochemical reagent for studying amino acid metabolism, chiral recognition, and enzyme activity in laboratory research.
Safety-wise, it is generally recognized as safe under normal handling, with mild irritation potential to the skin, eyes, and respiratory tract upon direct contact. It should be handled in a well-ventilated area with appropriate protective equipment. It should be stored in a sealed, cool, dry, and dark environment at 2-8℃, away from oxidants, moisture, and high temperatures to prevent decomposition and maintain purity. With its unique chiral characteristics and versatile applications, it is an indispensable raw material in pharmaceutical and life science fields.
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