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246948

Sigma-Aldrich

(R)-(+)-1,1′-Bi(2-naphthol)

99%

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

Assay

99%

form

solid

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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1 of 4

This Item
1046553824268.14774
1,1′-Bi-2-naphthol 99%

Sigma-Aldrich

104655

1,1′-Bi-2-naphthol

form

solid

form

-

form

-

form

powder

optical activity

[α]21/D +34°, c = 1 in THF

optical activity

-

optical activity

[α]20/D +157°, c = 1 in pyridine

optical activity

-

mp

208-210 °C (lit.)

mp

214-217 °C (lit.)

mp

242-244 °C (lit.)

mp

203-207 °C

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

200

optical purity

ee: 99% (HPLC)

optical purity

-

optical purity

ee: 99% (HPLC)

optical purity

-

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

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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)
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%.
Catalytic asymmetric epoxidation with (Salen) manganese (III) complex bearing binaphthyl groups of axial chirality.
Sasaki, H. et al.
Synlett, 1993(04), 300-300 (1993)
Noyori, R. et al.
Journal of the American Chemical Society, 106(22), 6709-6709 (1984)

Articles

BINOL and Derivatives

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