Skip to Content
MilliporeSigma
All Photos(2)

Documents

457701

Sigma-Aldrich

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

1 M in toluene

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

Sign Into View Organizational & Contract Pricing
All Photos(2)

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:
24869386
NACRES:
NA.22

concentration

1 M in toluene

bp

111 °C

density

0.929 g/mL at 25 °C

storage temp.

room temp

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

Looking for similar products? Visit Product Comparison Guide

Application

CBS Catalysts for Asymmetric Reduction and Asymmetric Synthesis
(S)-(-)-2-Methyl-CBS-oxazaborolidine solution [1M in toluene] may be used as a catalyst in the multi-step synthesis of (-)-diospongin A.
It may also be used in the preparation of:
  • (1S)-2-azido-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol
  • (R)-α-deuteriobenzyl alcohol
  • (R)-2-(1-hydroxyethyl)benzo[b]thiophene
Catalyst employed in an enantioselective synthesis of (S)-2-amino-1-phenylethanol.
Excellent catalyst for 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.

Other Notes

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

Acute Tox. 4 Oral - 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

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 1

1 of 1

Borane tetrahydrofuran complex solution 1.0 M in THF

Sigma-Aldrich

176192

Borane tetrahydrofuran complex solution

Enantioselective synthesis of (S)-salmeterol via asymmetric reduction of azidoketone by Pichia angusta.
Procopiou PA, et al.
Tetrahedron Asymmetry, 12(14), 2005-2008 (2001)
Diastereoselective photochromism of a bisbenzothienylethene governed by steric as well as electronic interactions.
Yokoyama Y, et al.
Journal of the American Chemical Society, 125(24), 7194-7195 (2003)
Organic Process Research & Development, 10, 893-893 (2006)
Singh, V. K.
Synthesis, 605-605 (1992)
Bis (oxazoline)-ligand-mediated asymmetric [2, 3]-Wittig rearrangement of benzyl ethers: reaction mechanism based on the hydrogen/deuterium exchange effect.
Kitamura M, et al.
Tetrahedron, 68(22), 4280-4285 (2012)
View All Related Papers

Articles

CBS Catalysts

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.

Asymmetric Catalysis with Chiral Oxazaborolidinium Ions (COBIs)

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