Methyl (R)-3-chloroserinate hydrochloride

Updated: 2026-07-16

Overview

Methyl (R)-3-chloroserinate hydrochloride is a chiral organic compound derived from serine, commonly used as an intermediate in pharmaceutical synthesis. Its unique structure makes it valuable for producing enantiomerically pure drugs and peptides. The compound is typically synthesized through chlorination and esterification of serine derivatives, followed by hydrochloride salt formation. Due to its chiral nature, the (R)-enantiomer is often preferred in asymmetric synthesis and drug development. The hydrochloride salt form enhances stability and solubility, making it easier to handle in laboratory and industrial settings. This compound is primarily supplied to pharmaceutical companies and research institutions.

Physical and Chemical Properties

Methyl (R)-3-chloroserinate hydrochloride appears as a white to off-white crystalline powder. It is hygroscopic, meaning it readily absorbs moisture from the air, which necessitates careful storage. The compound is soluble in water and polar organic solvents such as methanol and ethanol, facilitating its use in various reaction conditions. Its molecular formula is C4H8ClNO3·HCl, with a molecular weight of approximately 190.03 g/mol. The presence of both a chlorinated side chain and an ester group makes it reactive under certain conditions. The compound's chiral center at the 3-position is critical for its application in stereoselective synthesis.

Main Applications

The primary use of Methyl (R)-3-chloroserinate hydrochloride is as a building block in the synthesis of pharmaceuticals, particularly peptides and chiral drugs. It serves as an intermediate in the production of active pharmaceutical ingredients (APIs) where the (R)-configuration is required for biological activity. In biochemical research, this compound is employed to study enzyme mechanisms and protein interactions due to its ability to mimic natural amino acids. It is also utilized in the development of prodrugs and targeted therapies, where its chiral properties enhance drug efficacy and reduce side effects.

Safety and Storage

Methyl (R)-3-chloroserinate hydrochloride should be handled with care to avoid exposure. Protective equipment such as gloves, goggles, and lab coats are recommended. The compound may cause irritation upon contact with skin or eyes, and inhalation of dust should be avoided. Storage conditions are critical to maintaining the compound's stability. It should be kept in a tightly sealed container in a cool, dry place, preferably under inert gas or vacuum to prevent moisture absorption. Long-term storage at low temperatures (e.g., 2-8°C) is advisable to preserve its chemical integrity.

B2B Procurement Guide

When procuring Methyl (R)-3-chloroserinate hydrochloride, B2B buyers should prioritize suppliers with a proven track record in chiral compounds. Key considerations include purity (typically ≥98%), chiral purity (≥99% enantiomeric excess), and batch-to-batch consistency. Request certificates of analysis (CoA) and material safety data sheets (MSDS) to verify quality and safety specifications. Pricing varies depending on quantity and supplier, with bulk purchases often offering cost advantages. Lead times can be significant due to the specialized nature of the compound, so advance planning is recommended.