246956

(S)-(−)-1,1′-Bi(2-naphthol)

99%

• Synonym(e): (S)-(−)-1,1′-Binaphthalin-2,2′-diol, (S)-(−)-2,2′-Dihydroxy-1,1′-binaphthalin, (S)-BINOL
• Lineare Formel: HOC₁₀H₆C₁₀H₆OH
• CAS-Nummer: 18531-99-2
• Molekulargewicht: 286.32
• Beilstein: 4296068
• MDL-Nummer: MFCD00004068
• UNSPSC-Code: 12352005
• PubChem Substanz-ID: 24854838
• NACRES: NA.22

Eigenschaften

• Qualitätsniveau: 100
• Assay: 99%
• Optische Aktivität: [α]22/D −34°, c = 1 in THF
• Optische Reinheit: ee: 99% (HPLC)
• mp (Schmelzpunkt): 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
• InChIKey: PPTXVXKCQZKFBN-UHFFFAOYSA-N

Beschreibung

Anwendung

(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.

Sicherheitshinweise

• Piktogramme: GHS07
• Signalwort: Warning
• H-Sätze: H315,H319
• P-Sätze: P264 - P280 - P302 + P352 - P305 + P351 + P338 - P332 + P313 - P337 + P313
• Gefahreneinstufungen: Eye Irrit. 2 - Skin Irrit. 2
• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 3
• Persönliche Schutzausrüstung: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges