246956

(S)-(−)-1,1′-Bi(2-naphthol)

99%

• Synonym(s): (−)-2,2′-Dihydroxy-1,1′-dinaphthyl, (S)-(−)-1,1′-Binaphthalene-2,2′-diol, (S)-BINOL
• Linear Formula: HOC₁₀H₆C₁₀H₆OH
• CAS Number: 18531-99-2
• Molecular Weight: 286.32
• Beilstein/REAXYS Number: 4296068
• MDL number: MFCD00004068
• UNSPSC Code: 12352005
• PubChem Substance ID: 24854838
• NACRES: NA.22

Properties

• assay: 99%
• optical activity: [α]22/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

(S)-BINOL ligand in combination with titanium(IV) isopropoxide, forms (S)-(-)-BINOL-Ti complex, which is an effective chiral catalyst for:

• asymmetric addition of alkynylzinc to unactivated ketones
• enantioselective ring-opening reaction of meso-stilbene oxide and cyclohexene oxide with anilines
• asymmetric aryl transfers from triaryl(tetrahydrofuran)aluminum reagents to a wide variety of ketones

It can also react with zirconium(IV) isopropoxide isopropanol complex to form a chiral Lewis acid catalyst for the facile enantioselective allylation of aldehydes by allyltributyltin.

Precursor to phosphoramidite catalyst employed in a conversion of allylic alcohols to allylic amines.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319
• pcodes: P264 - P280 - P302 + P352 - P305 + P351 + P338 - P332 + P313 - P337 + P313
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• ppe: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges