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 (S)-(+)-Glycidyl Butyrate (CAS 65031-96-1) :
Chemical Identity:
Systematic Name: [(2S)-Oxiran-2-yl]methyl butanoate
Common Names: (S)-(+)-Glycidyl butyrate; (S)-Glycidyl butanoate; (+)-Glycidyl butyrate; (S)-(-)-2,3-Epoxypropyl butyrate (Note: The sign of optical rotation (+/-) can depend on solvent and concentration, but (S)-configuration is clearly specified) .
CAS Registry Number: 65031-96-1
Molecular Formula: C₇H₁₂O₃
Molecular Weight: 144.17 g/mol
Structure: CH₃(CH₂)₂C(=O)OCH₂- epoxide ring (Specifically the (S)-enantiomer at the epoxide carbon). Contains both an epoxide (oxirane) ring and an ester functional group (butyrate).
Stereochemistry:
Configuration: (S)-enantiomer at the chiral carbon atom of the glycidyl moiety (C2 of the oxirane ring).
Optical Activity: Typically dextrorotatory (+) at the sodium D line (specific rotation [α]D²⁰ ≈ +5° to +10°, exact value depends on concentration, solvent, and purity). This high enantiomeric purity (typically >97% ee or ≥98%) is a critical product specification.
Physical Properties:
Appearance: Usually a colorless to pale yellow liquid.
Odor: Characteristic ester-like odor.
Density: ~1.04 - 1.06 g/mL at 25°C.
Boiling Point: Decomposes before boiling at atmospheric pressure. Boils around 85-90°C at 10 mmHg / ~29°C at 18 mmHg (reported values vary).
Refractive Index (nD²⁰): ~1.425 - 1.435.
Solubility: Miscible with most common organic solvents (dichloromethane, chloroform, acetone, ethanol, ethyl acetate, diethyl ether, toluene). Very low solubility in water (hydrolyzes slowly).
Chemical Properties:
Key Functional Groups: Ester (Butyrate) and Epoxide (Oxirane) groups.
Reactivity:
Epoxide Ring: Highly reactive. Undergoes nucleophilic ring-opening reactions readily with nucleophiles such as amines, alcohols, thiols, carboxylates, carbanions, and halides. Acid or base catalyzed. Stereochemistry is often retained/inverted predictably at the chiral center, making it valuable for asymmetric synthesis.
Ester Group: Can undergo hydrolysis (acidic or basic), transesterification, aminolysis, or reduction (though the epoxide is usually more reactive). Hydrolysis in water is slow but occurs.
Stability: Sensitive to moisture (hydrolysis), acids, and bases. Stable under inert atmosphere at low temperatures. Avoid prolonged storage; use promptly after opening.
Handling & Safety (CRITICAL):
Hazards:
Toxicity: Toxic if swallowed, in contact with skin, or if inhaled. Skin and eye contact cause severe irritation and burns.
Sensitization: Skin sensitizer (can cause allergic skin reaction).
Mutagenicity: Glycidyl esters (like this one) are suspected mutagens and probable carcinogens. They are potent alkylating agents due to the strained epoxide ring.
Corrosivity: Can be corrosive to skin, eyes, and respiratory tract.
Flammability: Combustible liquid.
Precautions:
Handle ONLY in a well-ventilated fume hood.
Wear appropriate PPE: Nitrile or neoprene gloves, chemical splash goggles, lab coat.
Avoid contact with skin, eyes, and clothing. Avoid inhalation of vapor or mist.
Use explosion-proof equipment if handling larger quantities.
STRICT HYGIENE MEASURES REQUIRED.
Storage: Store tightly sealed under inert atmosphere (e.g., N₂ or Argon) at refrigerated temperatures (2-8°C). Protect from moisture, heat, and light. Keep away from acids, bases, oxidizing agents, and sources of ignition. Store in original container or clearly labeled compatible container. Limited shelf life – monitor purity.
Primary Applications:
Chiral Building Block/Synthon: Its primary use is as a versatile chiral electrophile in organic synthesis, particularly in the pharmaceutical and agrochemical industries.
Stereoselective Synthesis: Used to introduce chiral glycidyl moieties into target molecules via regioselective and stereospecific ring-opening reactions with various nucleophiles (e.g., amines to make β-amino alcohols, alcohols to make β-hydroxy ethers). The (S)-configuration allows access to specific enantiomers of complex molecules.
Pharmaceutical Intermediates: Key chiral intermediate in the synthesis of active pharmaceutical ingredients (APIs), especially beta-blockers (e.g., analogs of propranolol), other cardiovascular agents, and potentially other bioactive molecules.
Fine Chemical Synthesis: Used in the synthesis of chiral ligands, catalysts, and specialty polymers.
Derivatization Agent: Potential use in modifying polymers or biomolecules via the reactive epoxide group.
Research Chemical: Used in academic and industrial research labs studying asymmetric synthesis, epoxide reactivity, or developing new synthetic methodologies.
