457698

(R)-(+)-2-Methyl-CBS-oxazaborolidine solution

1 M in toluene

• Synonym(s): α,α-Diphenyl-D-prolinolmethylboronic acid cyclamide ester, (R)-1-Methyl,3,3-diphenyl-tetrahydro-pyrrolo(1,2-c)(1,3,2)oxazaborole, (R)-Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole
• Empirical Formula (Hill Notation): C₁₈H₂₀BNO
• CAS Number: 112022-83-0
• Molecular Weight: 277.17
• MDL number: MFCD00078440
• UNSPSC Code: 12352005
• PubChem Substance ID: 24869385
• NACRES: NA.22

Properties

• Quality Level: 200
• concentration: 1 M in toluene
• bp: 111 °C
• density: 0.95 g/mL at 25 °C
• functional group: phenyl
• 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

Description

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.

Safety Information

• Pictograms: GHS02,GHS08,GHS05,GHS07
• 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: dust mask type N95 (US), Eyeshields, Gloves