(S)-(−)-1,1′-Bi(2-naphthol)

Name: (<I>S</I>)-(−)-1,1′-Bi(2-naphthol)
Brand: ALDRICH

99%

Synonym(s):

(−)-2,2′-Dihydroxy-1,1′-dinaphthyl, (S)-(−)-1,1′-Binaphthalene-2,2′-diol, (S)-BINOL

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About This Item

Linear Formula:

HOC₁₀H₆C₁₀H₆OH

CAS Number:

18531-99-2

Molecular Weight:

286.32

UNSPSC Code:

12352005

NACRES:

NA.22

PubChem Substance ID:

24854838

MDL number:

MFCD00004068

Beilstein/REAXYS Number:

4296068

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Properties

Quality Level

100

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.