147702-13-4

Basic information

• Product Name: (S)-VANOL
• Synonyms: (S)-VANOL;(R)-VANOL;(S)-3,3'-DIPHENYL-2,2'-BI(1-NAPHTHALOL);(R)-3,3'-DIPHENYL-2,2'-BI-1-NAPHTHALOL;(2S)-(-)-3,3'-DIPHENYL-[2,2'-BINAPHTHALENE]-1,1'-DIOL;(2R)-(+)-3,3'-DIPHENYL-[2,2'-BINAPHTHALENE]-1,1'-DIOL;(2R)-(+)-3,3'-Diphenyl-[2,2'-binaphthalene]-1,1'-diol,min.98%(R)-VANOL;(2R)-(+)-3,3''-DIPHENYL-[2,2''-BINAPHTHALENE]-1,1''-DIOL (R)-VANOL
• CAS NO: 147702-13-4
• Molecular Formula: C32H22O2
• Molecular Weight: 438.52
• Product Categories: BINOL Series;Chiral Oxygen
• Mol File: 147702-13-4.mol
• Article Data: 2

Chemical Properties

• Melting Point: 200-204 °C
• Boiling Point: 580.1°C at 760 mmHg
• Flash Point: 251.8°C
• Appearance: white to pale yellow/Powder
• Density: 1.251g/cm³
• Vapor Pressure: 4.69E-14mmHg at 25°C
• Refractive Index: 1.727
• Storage Temp.: 2-8°C
• PKA: 7.71±0.50(Predicted)
• CAS DataBase Reference: (S)-VANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-VANOL(147702-13-4)
• EPA Substance Registry System: (S)-VANOL(147702-13-4)

Safety Data

• Hazard Codes: Xi
• Statements: 37/38-41
• Safety Statements: 26-39
• WGK Germany: 3
• Hazardous Substances Data: 147702-13-4(Hazardous Substances Data)

Usage

Reaction

Chiral ligand used in catalytic asymmetric aziridination. Chiral ligand used in catalytic asymmetric aminoallylation of aldehydes.

Uses

VANOL has proven to be an excellent ligand in catalytic asymmetric Diels-Alder, imine aldol, and aziridination reactions.

InChI:InChI=1/C32H22O2/c33-31-25-17-9-7-15-23(25)19-27(21-11-3-1-4-12-21)29(31)30-28(22-13-5-2-6-14-22)20-24-16-8-10-18-26(24)32(30)34/h1-20,33-34H

Upstream product

• 30069-65-9 3-phenylnaphthalen-1-ol 
• 536-74-3 phenylacetylene 
• 103-80-0 phenylacetyl chloride 
• 604-44-4 4-chloronaphthalen-1-ol 

Downstream Products

• 586952-27-4 (dppe)Pt(S-VANOL) 

Relevant articles and documents

Enantiodivergent Kinetic Resolution of 1,1′-Biaryl-2,2′-Diols and Amino Alcohols by Dipeptide-Phosphonium Salt Catalysis Inspired by the Atherton–Todd Reaction

A highly enantiodivergent organocatalytic method is disclosed for the synthesis of atropisomeric biaryls via kinetic resolution inspired by a dipeptide-phosphonium salt-catalyzed Atherton–Todd (A-T) reaction. This flexible approach led to both R- and S-enantiomers by fine-tuning of bifunctional phosphonium with excellent selectivity factors (s) of up to 1057 and 525, respectively. The potential of newly synthesized O-phosphorylated biaryl diols was illustrated by the synthesis of axially chiral organophosphorus compounds. Mechanistic investigations suggest that the bifunctional phosphonium halide catalyst differentiates between the in-situ-generated P-species in the A-T process, mainly involving phosphoryl chloride and phosphoric anhydride, thus leading to highly enantiodivergent O-phosphorylation reactions. Furthermore hydrogen bonding interactions between the catalysts and phosphorus molecules were crucial in asymmetric induction.