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674656 Sigma-Aldrich

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

1 M in THF

Synonym: 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

  • CAS Number 112022-83-0

  • Empirical Formula (Hill Notation) C18H20BNO

  • Molecular Weight 277.17

  •  MDL number MFCD00078440

  •  PubChem Substance ID 24885228

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Reduction
Quality Level   100
optical activity   [α]22/D +76.8°, c = 1 in toluene
concentration   1 M in THF
refractive index   n20/D 1.4602
density   0.942 g/mL at 25 °C
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

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.

Packaging

5, 25 mL in glass bottle

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Target organs 
Respiratory system
Supplemental Hazard Statements 
EUH019
RIDADR 
UN 2056 3 / PGII
WGK Germany 
WGK 3
Flash Point(F) 
1.4 °F - closed cup - Not applicable
Flash Point(C) 
-17 °C - closed cup - Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

CBS Oxazaborolidines

Since 1987, the series of chiral oxazaborolidines known as CBS catalysts (after Corey, Bakshi, and Shibata) have been used for the catalytic reduction of prochiral ketones, imines, and oximes to prod...
Aldrich ChemFiles 2007, 7.9, 20.
Keywords: Asymmetric synthesis, Catalysis, Chemfiles, Reductions

Peer-Reviewed Papers
15

References

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