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:
Molecular Weight:
286.32
PubChem Substance ID:
UNSPSC Code:
12352104
NACRES:
NA.22
EC Index Number:
606-048-4
Beilstein/REAXYS Number:
3616837
MDL number:
Quality Level
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
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.
signalword
Warning
hcodes
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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Articles
We present an article concerning BINOL and Derivatives.
我们展示了一篇有关BINOL及其衍生物的文章。
Noyori, R. et al.
Journal of the American Chemical Society, 106(22), 6709-6709 (1984)
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)
New chiral binaphthalene-derived iminium salt organocatalysts for asymmetric epoxidation of alkenes.
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%.
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 246948-10G | 04061825883700 |
| 246948-1G | 04061825883717 |
| 246948-5G | 04061825883724 |