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674648

Sigma-Aldrich

(S)-(−)-2-Methyl-CBS-oxazaborolidine solution

1 M in THF

Synonym(s):

α,α-Diphenyl-L-prolinol methylboronic acid cycl-amide ester, (S)-1-Methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2c][1,3,2]oxazaborole, (S)-3,3-Diphenyl-1-methyltetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole, (S)-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:
112022-81-8
Molecular Weight:
277.17
MDL number:
MFCD00078439
UNSPSC Code:
12352005
PubChem Substance ID:
24885227
NACRES:
NA.22

Quality Level

100

concentration

1 M in THF

refractive index

n20/D 1.460

density

0.942 g/mL at 25 °C

SMILES string

CB1OC([C@@H]2CCCN12)(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-/m0/s1

InChI key

VMKAFJQFKBASMU-KRWDZBQOSA-N

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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.

Signal Word

Danger

Hazard Classifications

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

Supplementary Hazards

EUH018 - EUH019

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

5.0 °F - closed cup

Flash Point(C)

-15 °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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Singh, V. K.
Synthesis, 605-605 (1992)
Cliff R Baar et al.
Journal of the American Chemical Society, 126(26), 8216-8231 (2004-07-01)
A series of enantiopure C1-symmetric metallocenes, [(SiMe2)2[eta5-C5H(CHMe2)2][eta5-C5H2((S)-CHMeCMe3)]]ZrCl2, (S)-2, [(SiMe2)2[eta5-C5H(CHEt2)2][eta5-C5H2((S)-CHMeCMe3)]]ZrCl2, (S)-6, and [(SiMe2)2[eta5-C5HCy2][eta5-C5H2((S)-CHMeCMe3)]]ZrCl2, (S)-7 (Cy = cyclohexyl), zirconocene dichlorides that have an enantiopure methylneopentyl substituent on the "upper" cyclopentadienyl ligand, and diastereomerically pure precatalysts, [(SiMe2)2[eta5-C5H((S)-CHMeCy)(CHMe2)][eta5-C5H3]]ZrCl2, (S)-8a and (S)-8b, which have an
Corey, E. J. et al.
Journal of the American Chemical Society, 109, 5551-5551 (1987)
Angewandte Chemie (International Edition in English), 37, 1986-1986 (1998)
Sakai, T. et al.
Tetrahedron, 52, 233-233 (1996)
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