(R)-(+)-2-METHYL-CBS-OXAZABOROLIDINE 1M SOLUTION IN TOLUENE (C005B-008885)

Application

CBS Catalysts for Asymmetric Reduction and Asymmetric Synthesis

(R)-(+)-2-Methyl-CBS-oxazaborolidine solution [1M in toluene] may be used as a catalyst in the asymmetric borane reduction of perfluoroalkyl ketones.
It may also be used in the preparation of:

• (-)-diospongin B
• (1R)-2-azido-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol
• (S)-α-deuteriobenzyl alcohol
• (3S,4R,5S)-1-(trimethylsilyl)-4,5-epoxyhex-1-yn-3-ol

Excellent catalyst of asymmetric reductions.

The CBS (Corey-Bakshi-Shibata) oxazaborolidine catalyst has been used in the asymmetric reduction of prochiral ketones. Other applications include the enantioselective synthesis of α-hydroxy acids, α-amino acids, C₂ symmetrical ferrocenyl diols, and propargyl alcohols.
Used in a desymmetrizing reduction leading to (S)-4-hydroxycyclohexenone.

Physical form

Precipitate may form in storage, but does not affect product quality. Gently heat product to 80−90 °C under an inert atmosphere to redissolve solids.

Molecular Weight: 277.17. Empirical Formula: C₁₈H₂₀BNO. Quality Level: 200. concentration: 1 . M in toluene. bp: 111 . °C. density: 0.95 . g/mL . at 25 . °C. storage temp.: room temp. SMILES string: [H][C@]12CCCN1B(C)OC2(c3ccccc3)c4ccccc4. InChI: 1S/C18H20BNO/c1-19-20-14-8-13-17(20)18(21-19,15-9-4-2-5-10-15)16-11-6-3-7-12-16/h2-7,9-12,17H,8,13-14H2,1H3/t17-/m1/s1. InChI key: VMKAFJQFKBASMU-QGZVFWFLSA-N. Pictograms: GHS02,GHS05,GHS07,GHS08. Signal Word: Danger. Hazard Statements: H225 - H304 - H315 - H318 - H336 - H361d - H373 - H412. Precautionary Statements: P210 - P273 - P280 - P301 + P310 - P305 + P351 + P338 - P331. Hazard Classifications: Aquatic Chronic 3 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 2 - STOT SE 3. Target Organs: Central nervous system. Storage Class Code: 3 - Flammable liquids. WGK: WGK 3. Flash Point(F): 39.2 °F - closed cup. Flash Point(C): 4 °C - closed cup. Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter.