Manufacturer: Hangzhou Royalchem Co.,LTD.
Website: www.cnroyalchem.com
【 Providing a complete set of intermediates and impurities for Tedizolid 】
【 Providing a complete set of intermediates and impurities for Tedizolid 】
【 Providing a complete set of intermediates and impurities for Tedizolid 】
Here is a detailed product description for CAS 919081-42-8: (S)-3-(3-Fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one :
1. Chemical Identification: * CAS Registry Number: 919081-42-8 * Systematic Name: (S)-3-(3-Fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one * Common Names/Synonyms: * (S)-3-(3-Fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one * (S)-5-(Hydroxymethyl)-3-(3-fluorophenyl)oxazolidin-2-one * Rivaroxaban Key Chiral Intermediate * Rivaroxaban Intermediate S-isomer * (S)-Oxazolidinone intermediate for Rivaroxaban * Molecular Formula: C₁₀H₁₀FNO₃ * Molecular Weight: 211.19 g/mol
2. Structural Characteristics: * Core Structure: 5-Membered cyclic carbamate (oxazolidin-2-one ring). * Substituents: * A 3-fluorophenyl group attached to the nitrogen (N3) of the oxazolidinone ring. * A hydroxymethyl group (-CH₂OH) attached to the carbon (C5) of the oxazolidinone ring. * Stereochemistry: Contains a single chiral center at the C5 position of the oxazolidinone ring. The compound is specified as the (S)-enantiomer , which is the biologically relevant isomer for its primary application.
3. Physical Properties (Typical / Expected): * Appearance: White to off-white crystalline powder or solid. * Melting Point: Typically in the range of 95-105 °C (exact value can vary slightly depending on purity and crystallization conditions). * Solubility: * Soluble: In polar organic solvents like Dichloromethane (DCM), Chloroform, Acetone, Methanol, Ethanol, Ethyl Acetate (EtOAc), Dimethylformamide (DMF), Dimethyl sulfoxide (DMSO). * Sparingly Soluble / Insoluble: In water and non-polar solvents like hexane or petroleum ether. * Specific Rotation: Exhibits optical rotation due to its chiral center. The typical value for the (S)-enantiomer is around [α]²⁵D = +40° to +50° (c = 1, in Methanol or Ethanol). [Note: Exact value should be confirmed per batch analysis] . * Hygroscopicity: May have slight hygroscopic tendencies due to the hydroxyl group.
4. Chemical Properties: * Functional Groups: Contains an oxazolidinone ring (cyclic carbamate), a secondary alcohol (hydroxymethyl), and an aryl fluoride (3-fluorophenyl). * Reactivity: * The secondary hydroxyl group (-CH₂OH) is the primary site for chemical modification (e.g., esterification, oxidation, substitution). * The oxazolidinone ring is generally stable but can be hydrolyzed under strongly acidic or basic conditions. * The aryl fluoride is relatively unreactive under typical conditions used for modifying the alcohol. * Stability: Stable under ambient conditions when stored properly. Sensitive to strong acids, strong bases, and strong oxidizing agents. Stability data should be consulted for specific storage and handling.
5. Primary Application & Significance: * Key Chiral Intermediate: This compound is a crucial high-value intermediate in the synthesis of the blockbuster anticoagulant drug Rivaroxaban (Xarelto®) , a Factor Xa inhibitor. * Role in Synthesis: The chiral integrity at the C5 position introduced in this intermediate is essential for the biological activity of Rivaroxaban. The hydroxymethyl group (-CH₂OH) is specifically functionalized in subsequent synthetic steps to build the final Rivaroxaban molecule. The (S)-configuration is mandatory for efficacy.
6. Handling and Storage: * Storage: Store in a cool, dry place. Desiccate at 2-8 °C (refrigerated) or -20 °C for long-term storage under inert atmosphere (Nitrogen or Argon) to prevent moisture absorption and potential degradation. Keep container tightly closed. * Handling: Handle with appropriate personal protective equipment (PPE) including gloves, safety glasses, and lab coat. Use in a well-ventilated area or fume hood. Avoid contact with skin, eyes, and clothing. Avoid creating dust. Avoid ingestion and inhalation.
7. Safety Considerations: * Safety Data Sheet (SDS): A Safety Data Sheet specific to this compound from the supplier MUST be consulted and followed prior to handling. * Hazards: Hazard classification depends on the supplier and specific toxicological data. It may be classified as an irritant (skin, eyes). Dust may cause respiratory irritation. * Precautions: Practice good industrial hygiene. Wash hands after handling. Implement engineering controls like local exhaust ventilation.
