Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

677183

Sigma-Aldrich

(S)-(–)-α,α-Diphenyl-2-pyrrolidinemethanol trimethylsilyl ether

95%

Synonym(s):

(2S)-2-[Diphenyl[(trimethylsilyl)oxy]methyl]pyrrolidine, (S)-α,α-Diphenylprolinol trimethylsilyl ether, (S)-2-[Diphenyl(trimethylsilanyloxy)methyl]pyrrolidine

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C20H27NOSi
CAS Number:
848821-58-9
Molecular Weight:
325.52
MDL number:
MFCD08690083
UNSPSC Code:
12352005
PubChem Substance ID:
24885354
NACRES:
NA.22

Quality Level

100

Assay

95%

optical activity

[α]22/D -50°, c = 1 in chloroform

refractive index

n20/D 1.5513

density

1.0459 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

C[Si](C)(C)OC([C@@H]1CCCN1)(c2ccccc2)c3ccccc3

InChI

1S/C20H27NOSi/c1-23(2,3)22-20(19-15-10-16-21-19,17-11-6-4-7-12-17)18-13-8-5-9-14-18/h4-9,11-14,19,21H,10,15-16H2,1-3H3/t19-/m0/s1

InChI key

RSUHWMSTWSSNOW-IBGZPJMESA-N

Application

Organocatalyst for 3-component reactions, and Robinson annulation of α,β-unsaturated aldehydes.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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’.

Already Own This Product?

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

Visit the Document Library

Dieter Enders et al.
Nature, 441(7095), 861-863 (2006-06-17)
Efficient and elegant syntheses of complex organic molecules with multiple stereogenic centres continue to be important in both academic and industrial laboratories. In particular, catalytic asymmetric multi-component 'domino' reactions, used during total syntheses of natural products and synthetic building blocks
Chemical and Engineering News, June (2006)
Bor-Cherng Hong et al.
The Journal of organic chemistry, 72(22), 8459-8471 (2007-10-09)
The highly enantioselective organocatalytic Robinson annulation of alpha,beta-unsaturated aldehydes was achieved, catalyzed by l-proline and trialkylamines and providing the formal [4 + 2] cycloaddition adducts. Additionally, in some examples in the catalysis with diarylpyrrolinol silyl ethers, the reactions afforded the

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