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Merck
CN

654299

(R)-(+)-o-Tolyl-CBS-oxazaborolidine solution

0.5 M in toluene

Synonym(s):

(R)-(+)-3,3-Diphenyl-1-o-tolyl-tetrahydropyrrolo(1,2-c)(1,3,2)oxazaborole

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About This Item

Empirical Formula (Hill Notation):
C24H24BNO
CAS Number:
865812-10-8
Molecular Weight:
353.26
NACRES:
NA.22
PubChem Substance ID:
24884025
UNSPSC Code:
12352005
MDL number:
MFCD07369781

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InChI

1S/C24H24BNO/c1-19-11-8-9-16-22(19)25-26-18-10-17-23(26)24(27-25,20-12-4-2-5-13-20)21-14-6-3-7-15-21/h2-9,11-16,23H,10,17-18H2,1H3/t23-/m1/s1

SMILES string

[H][C@]12CCCN1B(OC2(c3ccccc3)c4ccccc4)c5ccccc5C

InChI key

XHMKFCAQQGBIPZ-HSZRJFAPSA-N

concentration

0.5 M in toluene

refractive index

n20/D 1.514

density

0.900 g/mL at 25 °C

functional group

phenyl

Application

CBS Catalysts for Asymmetric Reduction and Asymmetric Synthesis
When protonated with trifluoromethanesulfonimide, chiral oxazaborolidines generate chiral Lewis acids, which have demonstrated great utility in the enantioselective Diels-Alder reaction.

signalword

Danger

Hazard Classifications

Aquatic Chronic 3 - Asp. Tox. 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

危险化学品
易制毒化学品（3类）
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Certificates of Analysis (COA)

Lot/Batch Number
SHBL7902
SHBH0769V
SHBD7648V
22596DK
46796DJ

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Do Hyun Ryu et al.
Journal of the American Chemical Society, 125(21), 6388-6390 (2003-06-06)
The strong acid triflimide ((CF3SO2)2NH) protonates chiral oxazaborolidines to form superactive, stable, chiral Lewis acids which are highly effective catalysts for a wide variety of enantioselective Diels-Alder reactions, documented herein by more than 20 examples.
Santanu Mukherjee et al.
Organic letters, 12(3), 632-635 (2010-01-13)
Diels-Alder reactions of various combinations of maleimides and 1,3-dienes with cationic oxazaborolidines as catalysts have been shown to be highly efficient and enantioselective.
Stemmler, R.T.
Synlett, 997-997 (2007)

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.

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