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Merck
CN

246948

(R)-(+)-1,1′-Bi(2-naphthol)

99%

Synonym(s):

(+)-2,2′-Dihydroxy-1,1′-dinaphthyl, (R)-(+)-1,1′-Binaphthalene-2,2′-diol, (R)-BINOL

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About This Item

Linear Formula:
HOC10H6C10H6OH
CAS Number:
18531-94-7
Molecular Weight:
286.32
PubChem Substance ID:
24854837
UNSPSC Code:
12352104
NACRES:
NA.22
EC Index Number:
606-048-4
Beilstein/REAXYS Number:
3616837
MDL number:
MFCD00004068

Key Documents

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Product Name

(R)-(+)-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%

form

solid

optical activity

[α]21/D +34°, c = 1 in THF

optical purity

ee: 99% (HPLC)

mp

208-210 °C (lit.)

Quality Level

100

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Application

A chiral auxiliary used in the catalytic asymmetric oxidation of sulfides to sulfoxides. Chiral lanthanide triflates formed from binaphthol serve as catalysts for asymmetric Diels-Alder reactions. Derivatives of binaphthol have recently found use in asymmetric Claisen rearrangements and asymmetric epoxidations. The lithium aluminum hydride derivative of these diols (BINAP-H) has been used extensively for the reduction of ketones.
Chiral binapthol imminium salt precursor. Salts were used for an asymmetric epoxidation of olefins.

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

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ8772
MKCW3516
MKCT1737
MKCR8797
MKCQ1892

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Catalytic asymmetric epoxidation with (Salen) manganese (III) complex bearing binaphthyl groups of axial chirality.
Sasaki, H. et al.
Synlett, 1993(04), 300-300 (1993)
Asymmetric Diels-Alder reactions catalyzed by chiral lanthanide (III) trifluoromethanesulfonates. Unique structure of the triflate and stereoselective synthesis of both enantiomers using a single chiral source and a choice of achiral ligands.
S. Kobayashi et al.
Tetrahedron, 50(40), 11623-11623 (1994)
Philip C Bulman Page et al.
The Journal of organic chemistry, 72(12), 4424-4430 (2007-05-18)
A series of binaphthalene-fused azepinium salts has been generated and used as organocatalysts in the asymmetric epoxidation of unfunctionalized alkenes, giving rise to ees of up to 84%.
Asymmetric aza-Diels-Alder reaction catalyzed by boron reagent: Effect of biphenol and binaphthol ligand.
Hattori, K. Yamamoto, H.
Synlett, 1993(02), 129-129 (1993)
Catalytic asymmetric oxidation of sulfides to sulfoxides with tert-butyl hydroperoxide using binaphthol as a chiral auxiliary.
Komatsu N, et al.
The Journal of Organic Chemistry, 58, 4529-4529 (1993)
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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。

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