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457701

Sigma-Aldrich

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

1 M in toluene

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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
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

Quality Level

100

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

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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.

Signal Word

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

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Organic Process Research & Development, 10, 893-893 (2006)
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)
Enantioselective synthesis of (S)-salmeterol via asymmetric reduction of azidoketone by Pichia angusta.
Procopiou PA, et al.
Tetrahedron Asymmetry, 12(14), 2005-2008 (2001)
Stereoselective synthesis of (-)-diospongins A and B and their stereoisomers at C-5.
Kawai N, et al.
Tetrahedron, 63(37), 9049-9056 (2007)
Singh, V. K.
Synthesis, 605-605 (1992)
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.

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