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457701

(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

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About This Item

Empirical Formula (Hill Notation):
C18H20BNO
CAS Number:
112022-81-8
Molecular Weight:
277.17
NACRES:
NA.22
PubChem Substance ID:
24869386
UNSPSC Code:
12352005
MDL number:
MFCD00078439
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Quality Level

100

concentration

1 M in toluene

bp

111 °C

density

0.929 g/mL at 25 °C

functional group

phenyl

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

Application

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.
(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
CBS Catalysts for Asymmetric Reduction and Asymmetric Synthesis

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.

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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

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SHBH5749
SHBH6193
BGBC3278V
BGBC2333V
BGBB9926

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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.

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)
View All Related Papers

Global Trade Item Number

SKUGTIN
457701-25ML04061838127914
457701-5ML04061838127921