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677019 Sigma-Aldrich

(S)-α,α-Bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanol trimethylsilyl ether

97%

Synonym: (S)-α,α-[3,5-Bis(trifluoromethyl)phenyl]prolinol trimethylsilyl ether, (S)-2-[(Bis(3,5-bis(trifluoromethyl)phenyl)trimethylsilanyloxy)methyl]pyrrolidine, (S)-2-[(Bis(3,5-bis(trifluoromethyl)phenyl)trimethylsilyloxy)methyl]pyrrolidine

  • CAS Number 848821-61-4

  • Empirical Formula (Hill Notation) C24H23F12NOSi

  • Molecular Weight 597.51

  •  MDL number MFCD09750447

  •  PubChem Substance ID 24885347

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Proline-Based Organocatalysts
assay   97%
mp   48-56 °C
SMILES string   C[Si](C)(C)OC([C@@H]1CCCN1)(c2cc(cc(c2)C(F)(F)F)C(F)(F)F)c3cc(cc(c3)C(F)(F)F)C(F)(F)F
InChI   1S/C24H23F12NOSi/c1-39(2,3)38-20(19-5-4-6-37-19,13-7-15(21(25,26)27)11-16(8-13)22(28,29)30)14-9-17(23(31,32)33)12-18(10-14)24(34,35)36/h7-12,19,37H,4-6H2,1-3H3/t19-/m0/s1
InChI key   MOHRGTBNEJKFMB-IBGZPJMESA-N

Description

General description

(S)-α,α-Bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanol trimethylsilyl ether is a diarylprolinol silyl ether organocatalyst. It can catalyze a variety of bond-forming reactions such as C-C, C-N, C-O, C-S, and C-Hal in high yields and excellent levels of enantiocontrol.

Packaging

1, 5 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
230.0 °F - closed cup
Flash Point(C) 
> 110 °C - closed cup

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Aldrich ChemFiles 2007, 7.9, 3. | Proline Analogs

The first examples were reported in the mid-70s, when L-proline was applied to Robinson annulation reactions. However, the big potential of proline as an organocatalyst was discovered at the beginnin...
Aldrich ChemFiles 2007, 7.9, 3.
Keywords: Aldol condensation, Aldol reaction, Alkylations, Aminations, Annulations, Asymmetric synthesis, Building blocks, Catalysis, Chemfiles, Condensations, Cyclopropanations, Help, Mannich Reaction, Methods, Michael Addition, Organocatalysis, Robinson Annulation, transformation

Catalysts for Carbonylation

Professor Geoffrey Coates and co-workers at Cornell University have reported the preparation and use of catalysts composed of an oxophilic Lewis acid and a cobalt tetracarbonyl anion (1–3, Figure 1) ...
Aldrich ChemFiles 2007, 7.5, 3.
Keywords: Carbonylations, Catalysis, Eliminations, Ligands, Purification, Ring expansion, Solvents

Related Content

Jørgensen’s Organocatalysts in Chemical Sythesis

Introduction Professor Karl Anker Jørgensen and his group have developed (R)- and (S)-α,α-bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanol trimethylsilyl ether which serve as excellent chira...
Keywords: Aminations, Applications, Asymmetric synthesis, Catalysis, Epoxidations, Ligands, Nucleophilic additions

Peer-Reviewed Papers
15

References

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