(S)-(+)-Glycidyl butyrate RC00208

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.