246948

Sigma-Aldrich

(R)-(+)-1,1′-Bi(2-naphthol)

99%

Synonym(s):
(R)-BINOL, (+)-2,2′-Dihydroxy-1,1′-dinaphthyl, (R)-(+)-1,1′-Binaphthalene-2,2′-diol
Linear Formula:
HOC10H6C10H6OH
CAS Number:
Molecular Weight:
286.32
Beilstein/REAXYS Number:
3616837
MDL number:
PubChem Substance ID:
EC Index Number:
606-048-4
NACRES:
NA.22

Quality Level

assay

99%

optical activity

[α]21/D +34°, c = 1 in THF

optical purity

ee: 99% (HPLC)

mp

208-210 °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

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Related Categories

Application

Chiral binapthol imminium salt precursor. Salts were used for an asymmetric epoxidation of olefins.
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.

Packaging

1, 5 g in glass bottle
10 g in poly bottle

pictograms

Skull and crossbones

signalword

Danger

hazcat

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 Germany

WGK 3

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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)
Molecular design of a chiral Lewis acid for the asymmetric Claisen rearrangement.
Maruoka, K. et al.
Journal of the American Chemical Society, 117(3), 1165-1165 (1995)
Noyori, R. et al.
Journal of the American Chemical Society, 106(22), 6709-6709 (1984)
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)
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)

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