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677213 Sigma-Aldrich

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

technical grade

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

  • CAS Number 908303-26-4

  • Empirical Formula (Hill Notation) C24H23F12NOSi

  • Molecular Weight 597.51

  •  MDL number MFCD09750448

  •  PubChem Substance ID 24885357

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Proline-Based Organocatalysts
grade   technical grade
optical purity   enantiomeric excess: ≥99.0% (HPLC)
mp   46-55 °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-/m1/s1
InChI key   MOHRGTBNEJKFMB-LJQANCHMSA-N

Description

Application

Catalyst involved in:
• Cyclocondensation of enals with methylenepyrrolidines
• Organocatalytic additions of β-ketosulfoxides to conjugated aldehydes
• Organocatalytic aza-Michael reactions
• Stereoselective propargylic alkylation of propargylic esters with aldehydes
• Epoxidation or aziridination of α,β-unsaturated aldehydes and Feist-Benary reactions of 1,3-dicarbonyls

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

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