Overview
(S)-2-(3-Chlorophenyl)-2-hydroxyacetic acid is a chiral carboxylic acid derivative with a chlorine-substituted phenyl group. It serves as a critical intermediate in the synthesis of enantiomerically pure pharmaceuticals, particularly for drugs targeting central nervous system disorders. The compound's stereochemistry is essential for its biological activity, making it valuable in asymmetric synthesis. Chiral building blocks like this are increasingly demanded in the pharmaceutical industry due to stricter regulatory requirements for enantiopure drugs. Its production typically involves enzymatic resolution or asymmetric hydrogenation of precursors, followed by purification to achieve high optical purity.
Physical and Chemical Properties
The compound exhibits typical carboxylic acid properties, including acidity (pKa ~3-4) and reactivity with bases to form salts. Its crystalline structure ensures stability during storage, though hygroscopicity may require desiccants for long-term preservation. The chlorine atom at the meta position influences its electronic properties, slightly reducing solubility in nonpolar solvents compared to unsubstituted analogs. Thermal analysis shows decomposition above 200°C, making it unsuitable for high-temperature reactions. Spectroscopic data (e.g., 1H NMR: δ 7.3-7.5 ppm for aromatic protons) are used for quality verification. The hydroxyl group enables further derivatization through esterification or etherification reactions.
Main Applications
Primary use is in synthesizing chiral β-blockers or antidepressants, where the (S)-configuration often correlates with higher receptor affinity. It may serve as a precursor to ligands for asymmetric catalysis in industrial-scale API manufacturing. Some agrochemical formulations also incorporate this scaffold for herbicidal activity. In research, the compound aids in studying structure-activity relationships of chiral molecules. Recent patents highlight its utility in prodrug designs that improve blood-brain barrier penetration. Contract manufacturing organizations (CMOs) frequently source it for custom synthesis projects requiring FDA-compliant starting materials.
Safety and Storage
Classified as an irritant (GHS Category 2); safety data sheets (SDS) must accompany shipments. Spills should be neutralized with sodium bicarbonate and absorbed with inert material. Avoid contact with strong oxidizers due to potential exothermic reactions. Long-term storage stability exceeds 24 months when kept at 2-8°C in sealed amber glass containers. Nitrogen purging is recommended for bulk quantities to prevent oxidation. Regulatory status varies by region—EU REACH registration may be required for annual imports above 1 ton.
B2B Procurement Guide
Pharmaceutical-grade material should meet USP/EP impurity profiles (<0.15% total impurities). Key due diligence includes auditing supplier ISO 9001 certification and batch-to-batch consistency records. MOQs typically start at 100g, with lead times of 4-8 weeks for custom syntheses. Consider multi-kilogram contracts for price advantages (20-30% discount); split shipments may mitigate storage costs. Preferred payment terms include LC at sight for new suppliers. Logistics require temperature-controlled transport for tropical climates. Digital procurement platforms like ChemDirect offer real-time purity verification for spot purchases.
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