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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/REAXYS Number:
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

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2

Storage Class

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

wgk_germany

WGK 3

ppe

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

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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

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
Bixia Yao et al.
Journal of chromatography. A, 1216(28), 5429-5435 (2009-06-09)
In this work, the enantioseparations of 1,1'-bi-2-naphthol (BINOL) and its three derivatives were performed on an immobilized polysaccharide-based chiral stationary phase, Chiralpak IA, under normal-phase mode. The effects of the content of polar modifier in the mobile phase and the
Fengping Zhan et al.
Journal of chromatography. A, 1217(26), 4278-4284 (2010-05-15)
Enantioseparation of 1,1'-bi-2-naphthol (BINOL) was performed on a polysaccharide-based chiral stationary phase, Chiralcel OD-H, under normal-phase mode. The effects of polar modifier in the mobile phase on the retention, enantioseparation and elution order were investigated in detail. Solvent-induced reversal of
Na Ji et al.
Journal of the American Chemical Society, 128(27), 8845-8848 (2006-07-06)
Chiral sum-frequency (SF) spectroscopy that measures both the real and the imaginary components of the SF spectral response was demonstrated for the first time. It was based on interference of the SF signal with a dispersionless SF reference. Solutions of
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