MilliporeSigma
All Photos(3)

246956

Sigma-Aldrich

(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:
Molecular Weight:
286.32
Beilstein:
4296068
MDL number:
PubChem Substance ID:

Quality Level

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

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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[1]
  • enantioselective ring-opening reaction of meso-stilbene oxide and cyclohexene oxide with anilines[2]
  • asymmetric aryl transfers from triaryl(tetrahydrofuran)aluminum reagents to a wide variety of ketones[3]
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.[4]
Precursor to phosphoramidite catalyst employed in a conversion of allylic alcohols to allylic amines.[5]

Packaging

1, 5, 25 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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