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  • 677183 - (S)-(–)-α,α-Diphenyl-2-pyrrolidinemethanol trimethylsilyl ether

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677183 Sigma-Aldrich

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

95%

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

  • CAS Number 848821-58-9

  • Empirical Formula (Hill Notation) C20H27NOSi

  • Molecular Weight 325.52

  •  MDL number MFCD08690083

  •  PubChem Substance ID 24885354

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Proline-Based Organocatalysts, Reproducibility: Validated Products,
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

Description

Packaging

1, 5 g in glass bottle

Application

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

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) 
Not applicable
Flash Point(C) 
Not applicable

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

Peer-Reviewed Papers
15

References

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