Skip to Content
Merck
All Photos(3)

Documents

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

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Linear Formula:
HOC10H6C10H6OH
CAS Number:
18531-99-2
Molecular Weight:
286.32
Beilstein:
4296068
MDL number:
MFCD00004068
UNSPSC Code:
12352005
PubChem Substance ID:
24854838
NACRES:
NA.22

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

Looking for similar products? Visit Product Comparison Guide

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Highly Enantioselective Phenylacetylene Additions to Ketones Catalyzed by (S)-BINOL- Ti Complex.
Zhou Y, et al.
Organic Letters, 6(23), 4147-4149 (2004)
Facile Enantioselective Ring-Opening Reaction of meso Epoxides with Anilines Using (S)-(-)-BINOL-Ti Complex as a Catalyst.
Kureshy RI, et al.
European Journal of Organic Chemistry, 2006(5), 1303-1309 (2006)
Catalytic asymmetric synthesis promoted by a chiral zirconate: Highly enantioselective allylation of aldehydes
Bedeschi P, et al.
Tetrahedron Letters, 36(43), 7897-7900 (1995)
Highly Enantioselective Aryl Additions of [AlAr3 (thf)] to Ketones Catalyzed by a Titanium (IV) Catalyst of (S)-Binol.
Chen C-A, et al.
Angewandte Chemie (Weinheim an der Bergstrasse, Germany), 119(28), 5469-5472 (2007)
Iridium-catalyzed synthesis of primary allylic amines from allylic alcohols: sulfamic acid as ammonia equivalent.
Christian Defieber et al.
Angewandte Chemie (International ed. in English), 46(17), 3139-3143 (2007-03-14)
View All Related Papers

Articles

BINOL and Derivatives

We present an article concerning BINOL and Derivatives.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service