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 2,4,4,5,5-Pentamethyl-1,3,2-dioxaborolane (CAS 94242-85-0):
Product Name: 2,4,4,5,5-Pentamethyl-1,3,2-dioxaborolane
Synonyms:
Pentamethyl-1,3,2-dioxaborolane
4,4,5,5-Tetramethyl-2-(methoxy)-1,3,2-dioxaborolane (common misnomer - correct structure has five methyls)
Pinacolomethylboronate (less common)
(Methylboronic acid pentamethylene ester) (descriptive)
CAS Registry Number: 94242-85-0
Molecular Formula: C₇H₁₅BO₂
Molecular Weight: 141.99 g/mol
Appearance: Colorless to pale yellow liquid.
Odor: Characteristic mild, solvent-like odor.
Key Properties:
High Volatility: A distinguishing feature compared to many other boronic esters (e.g., pinacol boronate esters like B₂pin₂). Its lower molecular weight and structure make it relatively volatile.
Air & Moisture Stability: While boronic esters are generally more stable than boronic acids, this compound exhibits enhanced stability towards atmospheric moisture and oxygen compared to simpler alkylboronic esters , primarily due to the steric bulk provided by the five methyl groups hindering attack by water or oxygen. Important: It is still hydrolytically sensitive over time and should be handled/stored under inert atmosphere (Ar, N₂) for best results and long-term storage. Avoid prolonged exposure to air.
Reactivity: Functions as a source of the CH₃-B< (methylboryl) moiety. It participates in key organic transformations:
Transition Metal-Catalyzed Coupling Reactions: Used as a methyl transfer reagent in Suzuki-Miyaura cross-coupling reactions. Its volatility can be advantageous or disadvantageous depending on reaction setup/purification.
Matteson Homologation: A valuable reagent for homologating boronic esters via dichloromethyllithium intermediates.
Protodeboronation Studies: Used in mechanistic studies due to its volatility allowing easier analysis of side products.
Preparation of Methylboron Reagents: Serves as a precursor to other methyl-containing boron species.
Solubility: Soluble in common organic solvents such as diethyl ether, tetrahydrofuran (THF), dichloromethane (DCM), toluene, and hexanes. Sparingly soluble in water (reacts slowly).
Density: ~0.83 - 0.86 g/mL at 20°C (typical range).
Boiling Point: Typically ~102-106°C at atmospheric pressure, but highly dependent on purity . Often reported/distilled at reduced pressure (e.g., ~40-45°C @ 20 mmHg).
Refractive Index (n20/D): ~1.405 - 1.415 (typical range).
Flash Point: Low. Typically ~24-28°C (classified as Flammable Liquid, Category 2 ). Handle away from ignition sources.
Handling & Safety:
Flammability: Highly flammable liquid and vapor.
GHS Hazard Statements (Typical):
H225: Highly flammable liquid and vapor.
H315: Causes skin irritation.
H319: Causes serious eye irritation.
H335: May cause respiratory irritation.
Precautionary Statements (P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501): Handle with extreme care using appropriate personal protective equipment (PPE) including safety goggles, chemical-resistant gloves (e.g., nitrile), and lab coat. Use only in well-ventilated areas (preferably a fume hood). Avoid breathing vapors/mist. Ground containers during transfer. Keep away from heat, sparks, open flames, hot surfaces. Use explosion-proof equipment. Store in a tightly closed container under inert atmosphere (Ar, N₂). Store in a cool, well-ventilated place away from incompatible materials. Keep container tightly closed.
Incompatibilities: Strong oxidizing agents, strong acids, strong bases. Reacts slowly with water/moisture releasing boric acid and the corresponding diol derivative (2-methylbutane-2,3-diol). Reaction with water may generate flammable gases under certain conditions.
Stability: Stable under inert atmosphere at recommended storage temperatures. Moisture sensitive. Air sensitive over prolonged periods.
Storage:
Store under an inert gas atmosphere (Argon or Nitrogen).
Keep container tightly sealed.
Store in a cool (< 25°C), dry, well-ventilated place.
Protect from moisture and light.
Store away from incompatible materials and ignition sources.
Flammable liquids storage cabinet is recommended for larger quantities.
Applications:
Organic Synthesis: Primarily used as a volatile methylboron transfer reagent in:
Suzuki-Miyaura cross-coupling reactions for introducing methyl groups.
Matteson chain homologation reactions.
Study of protodeboronation mechanisms.
Preparation of specialized methylboron reagents.
Chemical Intermediate: Building block for complex organoboron molecules.
Research & Development: Valuable tool in synthetic methodology development, particularly where volatility is useful (e.g., distillation removal).
