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(R)-3,3'-Bis[4-(trifluoromethyl)phenyl]-[1,1'-binaphthalene]-2,2'-diol

  • CAS No. 791616-58-5

  • Cat. No. CS-0087220
  • Purity≥97%
  • MDL No.None

*For research and further manufacturing use only, not for direct human use.

(R)-3,3'-Bis[4-(trifluoromethyl)phenyl]-[1,1'-binaphthalene]-2,2'-diol|CS-0087220

Structure of 791616-58-5

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General Information

  • CAS No. 791616-58-5
  • Cat. No. CS-0087220
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C, protect from light, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₃₄H₂₀F₆O₂
  • Molecular Weight 574.51
  • Synonym(s) R-3,3'-bis[4-(trifluoroMethyl)phenyl]-[1,1'-Binaphthalene]-2,2'-diol
  • SMILES OC1=C(C2=C(C=CC=C3)C3=CC(C4=CC=C(C(F)(F)F)C=C4)=C2O)C5=C(C=CC=C5)C=C1C6=CC=C(C(F)(F)F)C=C6

Description

(R)-3,3'-Bis[4-(trifluoromethyl)phenyl]-[1,1'-binaphthalene]-2,2'-diol features a rigid chiral binaphthyl scaffold bearing electron-deficient trifluoromethylphenyl groups and strategically positioned diol functionalities. This configuration imparts high enantioselectivity in asymmetric catalysis, enabling efficient stereocontrol in transition metal-catalyzed reactions. The molecule exhibits excellent stability under standard bench conditions and demonstrates favorable solubility in organic solvents, facilitating its integration into complex reaction systems.

Application

(R)-3,3'-Bis[4-(trifluoromethyl)phenyl]-[1,1'-binaphthalene]-2,2'-diol serves as a chiral ligand scaffold in asymmetric catalysis, enabling enantioselective transformations through its rigid binaphthyl backbone and ortho-substituted aryl groups. The trifluoromethyl functionalities enhance electronic modulation and metabolic stability, while the diol motif provides robust coordination sites for transition metals. This compound exhibits excellent bench stability, facilitates straightforward purification, and is widely employed in established protocols for C–C and C–X bond formations.

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P280-P302+P352

Quality Control

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Computational Chemistry Data

  • TPSA   40.46
  • LogP   10.4428
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   3

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