246948

(R)-(+)-1,1′-Bi(2-naphthol)

99%

• Synonym(s): (+)-2,2′-Dihydroxy-1,1′-dinaphthyl, (R)-(+)-1,1′-Binaphthalene-2,2′-diol, (R)-BINOL
• Linear Formula: HOC₁₀H₆C₁₀H₆OH
• CAS Number: 18531-94-7
• Molecular Weight: 286.32
• Beilstein: 3616837
• MDL number: MFCD00004068
• UNSPSC Code: 12352104
• PubChem Substance ID: 24854837
• EC Index Number: 606-048-4
• NACRES: NA.22

Properties

• Quality Level: 100
• Assay: 99%
• form: solid
• optical activity: [α]21/D +34°, c = 1 in THF
• optical purity: ee: 99% (HPLC)
• mp: 208-210 °C (lit.)
• SMILES string: Oc1ccc2ccccc2c1-c3c(O)ccc4ccccc34
• InChI: 1S/C20H14O2/c21-17-11-9-13-5-1-3-7-15(13)19(17)20-16-8-4-2-6-14(16)10-12-18(20)22/h1-12,21-22H
• InChI key: PPTXVXKCQZKFBN-UHFFFAOYSA-N

Description

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 Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H315,H319
• Precautionary Statements: P264 - P280 - P302 + P352 - P305 + P351 + P338 - P332 + P313 - P337 + P313
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves