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Sigma-Aldrich

(R)-(+)-α,α-Diphenyl-2-pyrrolidinemethanol trimethylsilyl ether

96%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C20H27NOSi
CAS Number:
943757-71-9
Molecular Weight:
325.52
MDL number:
MFCD09265100
UNSPSC Code:
12352005
PubChem Substance ID:
24885355

Assay

96%

form

solid

optical activity

[α]22/D +52±5°, c = 1 in chloroform

refractive index

n20/D 1.5509

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-/m1/s1

InChI key

RSUHWMSTWSSNOW-LJQANCHMSA-N

Related Categories

General description

(R)-(+)-α,α-Diphenyl-2-pyrrolidinemethanol trimethylsilyl ether is a diarylprolinol silyl ether organocatalyst.

Application

(R)-(+)-α,α-Diphenyl-2-pyrrolidinemethanol trimethylsilyl ether can be used as a catalyst to synthesize:
  • Glycofused tricyclic derivatives, which are used in the development of amyloid β-peptide diagnostic tools.
  • Cyclohexene carbaldehyde derivatives by reacting benzoylnitromethane with aliphatic enals.

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

11 - Combustible Solids

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’.

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Organocatalytic Cascade Reaction of Aliphatic Enals and Benzoylnitromethane: Synthesis of Enantioenriched Tetrasubstituted Cyclohexene Carbaldehyde
David Rodriguez FA, et al.
Journal of Chemistry, 2020 (2020)
Synthesis and Preliminary Biological Evaluation of Fluorescent Glycofused Tricyclic Derivatives of Amyloid β-Peptide Ligands
D'Orazio G, et al.
European Journal of Organic Chemistry, 2016(9), 1660-1664 (2016)
The diarylprolinol silyl ether system: a general organocatalyst.
Jensen KL, et al.
Accounts of Chemical Research, 45(2), 248-264 (2011)

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