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674656

Sigma-Aldrich

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

1 M in THF

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

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About This Item

Empirical Formula (Hill Notation):
C18H20BNO
CAS Number:
Molecular Weight:
277.17
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

optical activity

[α]22/D +76.8°, c = 1 in toluene

Quality Level

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

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Application

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.

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - STOT SE 3

Target Organs

Central nervous system, Respiratory system

Supplementary Hazards

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

1.4 °F - closed cup

Flash Point(C)

-17 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Stemmler, R.T.
Synlett, 997-997 (2007)
Current Science, 78, 1314-1317 (2000)
Corey, E. J. et al.
Journal of the American Chemical Society, 109, 5551-5551 (1987)
Corey, E. J.; Link, J. O.
Tetrahedron Letters, 33, 3431-3431 (1992)
Schwink, L.; Knochel, P.
Tetrahedron Letters, 37, 25-25 (1996)

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