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104655

Sigma-Aldrich

1,1′-Bi-2-naphthol

99%

Synonym(s):

(±)-1,1′-Binaphthalene-2,2′-diol, (±)-2,2′-Dihydroxy-1,1′-dinaphthyl, 2,2′-Dihydroxybinaphthalene, 2,2′-Dihydroxydinaphthyl, 2,2′-Dinaphthol, BINOL

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About This Item

Linear Formula:
HOC10H6C10H6OH
CAS Number:
602-09-5
Molecular Weight:
286.32
Beilstein:
997518
EC Number:
210-014-0
MDL number:
MFCD00004068
UNSPSC Code:
12161600
PubChem Substance ID:
24846670
NACRES:
NA.22

Quality Level

200

Assay

99%

reaction suitability

reagent type: ligand

mp

214-217 °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

Application

Chiral ligand and auxiliary for asymmetric Michael addition reaction; enantioselective Diels-Alder reaction; alkynylation.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H315,H319

Hazard Classifications

Acute Tox. 3 Oral - 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

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Certificates of Analysis (COA)

Lot/Batch Number
WXBD2034V
WXBD4813V
WXBD3075V
WXBD2396V
WXBC9636V

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2,2′-Dibromo-1,1′-binaphthyl 96%

Sigma-Aldrich

676438

2,2′-Dibromo-1,1′-binaphthyl

Yifeng Zhou et al.
Organic letters, 6(23), 4147-4149 (2004-11-05)
The readily available and inexpensive (S)-BINOL ligand in combination with Ti(O(i)Pr)(4) is an effective chiral catalyst for the catalytic asymmetric addition of alkynylzinc to unactivated simple ketones. Good to excellent enantioselectivities were achieved. No previous case has been reported successfully
BINOL: a versatile chiral reagent.
Jean Michel Brunel
Chemical reviews, 105(3), 857-897 (2005-03-10)
Sang-Mi Jeong et al.
Journal of the American Chemical Society, 130(11), 3497-3501 (2008-02-22)
Monolayers of 1,1'-bi-2-naphthol (BN) derivatives, of which the two naphthalene rings are twisted along the carbon(1)-carbon(1') single bond, were studied for their conformational effect on the growth of pentacene crystals on their monolayer surface. BN monolayers with H and Br
Lei Shi et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 15(38), 9855-9867 (2009-08-18)
Well-designed, self-assembled, metal-organic frameworks were constructed by simple mixing of multitopic MonoPhos-based ligands (3; MonoPhos=chiral, monodentate phosphoramidites based on the 1,1'-bi-2-naphthol platform) and [Rh(cod)(2)]BF(4) (cod=cycloocta-1,5-diene). This self-supporting strategy allowed for simple and efficient catalyst immobilization without the use of extra
Liheng Feng et al.
Organic & biomolecular chemistry, 9(8), 2938-2942 (2011-03-08)
A glucose sensing switch is formed by water soluble conjugated polymer (PP-S-BINOL) and boronic acid-functionalized benzyl viologen (o-BBV). The two-component system shows a high sensitivity for glucose sensing with a 17-fold increase in the fluorescence intensity in the presence of
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