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246948 Aldrich

(R)-(+)-1,1′-Bi(2-naphthol)

99%

Synonym: (+)-2,2′-Dihydroxy-1,1′-dinaphthyl, (R)-(+)-1,1′-Binaphthalene-2,2′-diol, (R)-BINOL

  • CAS Number 18531-94-7

  • Linear Formula HOC10H6C10H6OH

  • Molecular Weight 286.32

  •  Beilstein Registry Number 3616837

  •  MDL number MFCD00004068

  •  PubChem Substance ID 24854837

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Properties

Related Categories Asymmetric Synthesis, BINOLs, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Privileged Ligands and Complexes More...
InChI Key   PPTXVXKCQZKFBN-UHFFFAOYSA-N
assay   99%
optical activity   [α]21/D +34°, c = 1 in THF
optical purity   ee: 99% (HPLC)
mp   208-210 °C(lit.)

Description

Packaging

1, 5 g in glass bottle

10 g in poly bottle

Application

A chiral auxiliary used in the catalytic asymmetric oxidation of sulfides to sulfoxides. Chiral lanthanide triflates formed from binaphthol serve as catalysts for asymmetric Diels-Alder reactions. Derivatives of binaphthol have recently found use in asymmetric Claisen rearrangements and asymmetric epoxidations. The lithium aluminum hydride derivative of these diols (BINAP-H) has been used extensively for the reduction of ketones.

Chiral binapthol imminium salt precursor. Salts were used for an asymmetric epoxidation of olefins.

Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
3
RTECS 
DU3106100

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Protocols & Articles

Articles

Indanols

These chiral imine-ligands have recently been used in the vanadium-catalyzed oxidation of sulfides in conjunction with hydrogen peroxide. Optically active sulfoxides are obtained in high yields and e...
Aldrich ChemFiles 2005, 5.4, 7.
Keywords: Asymmetric synthesis, Catalysis, Chemfiles, Ligands, Oxidations

Peer-Reviewed Papers
15

References

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