Skip to Content
Merck
CN

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

Sign In to View Organizational & Contract Pricing.

Select a Size

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

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Product Name

(S)-(−)-1,1′-Bi(2-naphthol), 99%

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

SMILES string

Oc1ccc2ccccc2c1-c3c(O)ccc4ccccc34

InChI key

PPTXVXKCQZKFBN-UHFFFAOYSA-N

assay

99%

optical activity

[α]22/D −34°, c = 1 in THF

optical purity

ee: 99% (HPLC)

mp

208-210 °C (lit.)

Quality Level

100

Looking for similar products? Visit Product Comparison Guide

Related Categories

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

signalword

Warning

hcodes

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCZ9788
MKCX7823
MKCT2124
MKCT7861
MKCS4168

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

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

Visit the Document Library

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)
Highly Enantioselective Phenylacetylene Additions to Ketones Catalyzed by (S)-BINOL- Ti Complex.
Zhou Y, et al.
Organic Letters, 6(23), 4147-4149 (2004)
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)
Catalytic asymmetric synthesis promoted by a chiral zirconate: Highly enantioselective allylation of aldehydes
Bedeschi P, et al.
Tetrahedron Letters, 36(43), 7897-7900 (1995)
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.

BINOL及其衍生物

我们展示了一篇有关BINOL及其衍生物的文章。

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