(R)-2-Methyl-CBS-oxazaborolidine, CAS No. 112022-83-0

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112022-83-0

Catalog No. EBD12122

CAS 112022-83-0

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

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Basic Information

Synonyms: (R)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole (R)-2-Methyl-CBS-oxazaborolidine (R)-Methyloxazaborolidine ALPHA,ALPHA-Diphenyl-D-PROLINOLMETHYLBORONICACIDCYCL-AMIDE-ESTER (R)-(+)-2-Methyl-CBS-oxazaborolidine (R)-1-Methyl,3,3-Diphenyl-TETRAHYDRO-PYRROLO(1,2-C)(1,3,2)oxazaborole (R)-3,3-Diphenyl-1-MethylTETRAHYDRO-1H,3H-PYRROLO[1,2-C][1,3,2]oxazaborole (R)-3,3-Diphenyl-1-MethylTETRAHYDRO-3H-PYRROLO-[1,2-C][1,3,2]oxazaborole (R)-5,5-Diphenyl-2-Methyl-3,4-PROPANO-1,3,2-oxazaborolidine (3aR)-1-methyl-3,3-diphenyltetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole (R)-Me-CBS (R)-(+)-2-Methyl-CBS-oxazaborolindine (R)-5,5-Diphenyl-2-Met

Molecular Formula: C18H20BNO

Molecular Weight: 277.17

MDL Number: MFCD00078440

Categories: Synthetic Chemistry > Catalysts and Ligands > Chiral Ligands Synthetic Chemistry > Basic Synthetic Reagents > Chiral Auxiliaries and Resolution Reagents

Product Description:

(R)-2-Methyl-CBS-oxazaborolidine is a well-defined, chiral organoboron catalyst. It is a derivative of the Corey-Bakshi-Shibata (CBS) catalyst family, characterized by its bicyclic oxazaborolidine structure with a methyl substituent on the carbon adjacent to the nitrogen. This compound is typically used as a pre-catalyst, which is activated in situ by a borane source such as BH₃·THF. Its primary and most significant application is as a highly enantioselective catalyst for the asymmetric reduction of prochiral ketones to produce chiral secondary alcohols. This reaction is a cornerstone in modern organic synthesis for constructing stereogenic centers. The (R)-enantiomer of the catalyst generally delivers the (R)-alcohol product from the reduction. It is renowned for its high efficiency, excellent enantioselectivity (often >99% ee), and broad substrate scope, making it indispensable in the synthesis of pharmaceuticals, agrochemicals, and fine chemicals where optical purity is critical. As a specialty chiral catalyst and auxiliary, it is not a commodity chemical but a high-value research and process chemistry reagent. Handling requires caution under inert atmosphere (e.g., nitrogen or argon) due to its sensitivity to moisture and air, which can lead to decomposition and loss of catalytic activity.

Physical Properties

Melting Point: 85-95 °C(lit.)

Boiling Point: 111 °C

Flash Point: 40 °F

Density: 0.95 g/mL at 25 °C

Refractivity: 68 ° (C=1, MeOH)

Storage: 2-8°C

Safety Information

Packing Level: II

Hazard Category: 3

Transport Codes: 2056

Analytical Data

Appearance: white to light yellow crystal powder