(S)-2-Methyl-CBS-oxazaborolidine, CAS No. 112022-81-8

Welcome to iChemical.com!

In the below part, please select the country you want us to ship to: Please note that once you've selected a shipping country, all pricing information on our website will be automatically updated to include door-to-door shipping to the country you specified.

North America

South America

Africa

Europe

Asia

Oceania

112022-81-8

Catalog No. EBD17012

CAS 112022-81-8

Name (S)-2-Methyl-CBS-oxazaborolidine

Get Quote

Basic Information

Synonyms: (S)-Methyloxazaborolidine (S)-3,3-Diphenyl-1-methyltetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole (S)-2-Methyl-CBS-oxazaborolidine (S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole (3aS)-1-methyl-3,3-diphenyltetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole (S)-Me-CBS (S)-(-)-2-Methyl-CBS-oxazaborolindine (s)-methyl-cbs (s)-cbsreagent

Molecular Formula: C18H20BNO

Molecular Weight: 277.17

MDL Number: MFCD00078439

Categories: Synthetic Chemistry > Catalysts and Ligands > Organocatalysts Synthetic Chemistry > Catalysts and Ligands > Chiral Ligands

Product Description:

(S)-2-Methyl-CBS-oxazaborolidine is a well-defined, chiral organoboron compound, specifically a 1,3,2-oxazaborolidine derivative. It is a highly effective and widely used chiral catalyst, commonly referred to as Corey-Bakshi-Shibata (CBS) catalyst. This compound is typically employed in substoichiometric amounts. Its primary and most significant application is in the enantioselective reduction of prochiral ketones to chiral secondary alcohols. It acts as a catalyst in conjunction with a borane source (e.g., BH₃•THF or catecholborane). The reaction proceeds via a transition state where the catalyst activates both the ketone and the borane, delivering hydride with high facial selectivity, often achieving enantiomeric excess (ee) values exceeding 95%. It is a cornerstone technology in asymmetric synthesis for the pharmaceutical and fine chemical industries. The catalyst is known for its robustness, predictability, and broad substrate scope. It is commercially available in both enantiomeric forms ((R) and (S)), allowing access to either enantiomer of the desired alcohol product. Proper handling requires caution as it is moisture-sensitive and is typically used under inert atmosphere conditions.

Physical Properties

Melting Point: 115-117°C

Boiling Point: 111 °C

Flash Point: 40 °F

Density: 0.93 g/mL at 20 °C(lit.)

Refractivity: -68 ° (C=1, MeOH)

Storage: Refrigerator

Analytical Data

Appearance: white or cream white solid