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Sigma-Aldrich

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

1 M in toluene

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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:
Molecular Weight:
277.17
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

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1 of 4

This Item
457701674656674648
bp

111 °C

bp

111 °C

bp

-

bp

-

density

0.95 g/mL at 25 °C

density

0.929 g/mL at 25 °C

density

0.942 g/mL at 25 °C

density

0.942 g/mL at 25 °C

concentration

1 M in toluene

concentration

1 M in toluene

concentration

1 M in THF

concentration

1 M in THF

Application

(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.

signalword

Danger

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

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

39.2 °F - closed cup

flash_point_c

4 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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Articles

we are pleased to offer both enatiomers of 2-methyl-CBS-oxazaborolidine as a dry reagent, in addition to our current offerings as a 1M solution in toluene.

Learn about the applications of chiral oxazaborolidinium ions (COBIs) as Lewis acid catalysts in different asymmetric reactions such as cyclopropanation, epoxidation, and radical reactions along with details of their catalytic action.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service