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 (R)-Glycidyl butyrate (CAS No. 60456-26-0):
1. Chemical Identity & Structure:
Systematic Name: (2R)-2-[(Butanoyloxy)methyl]oxirane
Synonyms: (R)-(-)-Glycidyl butyrate; (R)-Oxiran-2-ylmethyl butanoate; (R)-Glycidol butyrate
CAS Registry Number: 60456-26-0
Molecular Formula: C₇H₁₂O₃
Molecular Weight: 144.17 g/mol
Structure:
An epoxide ring (oxirane) with a (CH₂OCO(CH₂)₂CH₃) group attached to one carbon.
Features a chiral center at the carbon adjacent to the epoxide oxygen (C2 of the oxirane). The (R) designation specifies the absolute configuration at this stereocenter.
Functional Groups: Epoxide + Ester (butyrate).
2. Physical Properties:
Appearance: Typically a clear, colorless to pale yellow liquid.
Odor: Characteristic ester-like odor.
Boiling Point: Approximately 180-185 °C (at atmospheric pressure; may vary slightly). Often handled/distilled under reduced pressure due to thermal sensitivity.
Density: ~1.0 g/cm³ (estimated).
Refractive Index: Typically ranges from 1.420 - 1.430 (nD²⁰).
Solubility: Moderately soluble in most common organic solvents (e.g., ethanol, diethyl ether, acetone, chloroform, ethyl acetate). Very low solubility in water.
Optical Rotation: Exhibits a characteristic negative optical rotation (levorotatory). Specific rotation values like [α]D²⁰ = -14° to -18° (c=1 in chloroform) are common for the enantiopure (R) -form, distinguishing it from the racemate or (S) -enantiomer.
3. Chemical Properties & Reactivity:
Epoxide Reactivity: The highly strained 3-membered epoxide ring makes this compound a potent electrophile. It readily undergoes ring-opening reactions with various nucleophiles (e.g., amines, thiols, alcohols, water, carboxylates, carbanions). Regiochemistry and stereochemistry of ring-opening are often controlled by the chiral center and reaction conditions.
Ester Group: Can undergo typical ester reactions like hydrolysis (acidic or basic), transesterification, or aminolysis, although the epoxide ring is generally more reactive.
Stability:
Thermal: Can polymerize upon heating, especially if impurities are present or without stabilizers.
Chemical: Sensitive to strong acids and bases (can catalyze ring-opening or hydrolysis). Moisture-sensitive.
Storage: Requires storage under inert atmosphere (e.g., nitrogen or argon), in tightly sealed containers, protected from light, and preferably refrigerated (2-8°C) to minimize racemization, hydrolysis, and polymerization. Often contains stabilizers (e.g., BHT).
4. Key Applications:
Chiral Building Block/Synthon: Its primary value lies in its enantiomeric purity ( R configuration).
Used in the stereoselective synthesis of complex bioactive molecules, particularly pharmaceuticals and agrochemicals, where the chirality is crucial for biological activity.
Classic Example: Key intermediate in the synthesis of enantiomerically pure beta-blockers (e.g., (S) -Propranolol, (S) -Metoprolol). The (R) -glycidyl ester reacts regioselectively and stereospecifically with the appropriate aryloxyamine under controlled conditions.
Asymmetric Synthesis: Serves as a precursor for introducing chiral glycidyl groups or chiral 3-substituted-1,2-propanediol derivatives via regioselective nucleophilic ring-opening.
Polymer Chemistry: Can be used as a reactive diluent or monomer in epoxy resin formulations, potentially imparting specific properties due to the chiral center and butyrate chain. Requires careful formulation due to stability concerns.
Research Chemical: Used in organic synthesis research focused on developing new stereoselective reactions involving epoxides.
5 . Handling, Safety & Hazards:
Toxicity: Classified as harmful or toxic if swallowed, inhaled, or absorbed through skin. Epoxides are known skin and eye irritants/sensitizers and suspected carcinogens/mutagens.
Flammability: Flammable liquid.
Reactivity Hazard: The epoxide ring presents a reactivity hazard. Contact with strong oxidizing agents, acids, or bases should be avoided.
Personal Protective Equipment (PPE): Essential. Use in a well-ventilated fume hood. Wear nitrile or neoprene gloves, safety goggles, and lab coat. Respiratory protection may be necessary depending on handling conditions.
Storage: Store tightly sealed under inert gas at 2-8°C. Keep away from heat, sparks, open flames, and incompatible materials (strong acids, bases, oxidizers).
Disposal: Dispose of as hazardous waste according to local, regional, and national regulations.
GHS Hazard Statements (Examples): H226 (Flammable liquid), H302+H312+H332 (Harmful if swallowed, in contact with skin or if inhaled), H314 (Causes severe skin burns and eye damage), H317 (May cause an allergic skin reaction), H341 (Suspected of causing genetic defects), H350 (May cause cancer).
Precautionary Statements: P201, P202, P280, P301+P310+P330, P303+P361+P353, P304+P340+P312, P305+P351+P338, P308+P313.
