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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

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

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’.

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2,2′-Dibromo-1,1′-binaphthyl 96%

Sigma-Aldrich

676438

2,2′-Dibromo-1,1′-binaphthyl

BINOL: a versatile chiral reagent.
Jean Michel Brunel
Chemical reviews, 105(3), 857-897 (2005-03-10)
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
Wen Weng et al.
Journal of chromatography. A, 1210(2), 178-184 (2008-10-07)
Seven binaphthyl compounds were enantioseparated by HPLC with an immobilized polysaccharide-based chiral stationary phase, Chiralpak IA. The experiments were performed under normal-phase conditions. Effects of polar modifier and column temperature on the retention time and separation factor were evaluated. All
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
Andrew C Meng et al.
Journal of molecular recognition : JMR, 22(2), 121-128 (2009-02-06)
One monomer molecularly imprinted polymers (OMNiMIPs) have enhanced binding and selectivity properties versus traditionally formulated ethylene glycol dimethacrylate (EGDMA)/methacrylic acid (MAA) imprinted polymers. Further comparison was investigated toward multi-analyte imprinting capability of these two imprinted materials. Two templates, (R)-(+)-1,1'-bi-2-naphthol and
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