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18531-94-7 - (R)-(+)-1,1'-Bi(2-naphthol), 99% - (R)-(+)-1,1'-Binaphthalene-2,2'-diol - (R)-(+)-BINOL - L08305 - Alfa Aesar

L08305 (R)-(+)-1,1'-Bi(2-naphthol), 99%

CAS Number
18531-94-7
Synonyms
(R)-(+)-1,1'-Binaphthalene-2,2'-diol
(R)-(+)-BINOL

Size Price ($) Quantity Availability
1g 32.96
5g 93.32
25g 294.30
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(R)-(+)-1,1'-Bi(2-naphthol), 99%

MDL
MFCD00004068

Chemical Properties

Formula
C20H14O2
Formula Weight
286.33
Melting point
206-211°
Density
1.301
Optical Rotation
+34.5 (c=1 in THF)
Solubility
Insoluble in water. Solubility in THF within almost transparency). Soluble in dioxane 50 mg/mL.

Applications

It is used in biosynthetic preparation for enantioselective oxidation of naphthols to binaphthyldiols with horseradish peroxidase catalyst. 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.5 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.

Notes

Store away from oxidizing agents. Keep the container tightly closed and place it in a cool, dry and well ventilated condition.

Literature References

Lilia Kurz, et al. Stereospecific functionalization of (R)-(-)-1,1?-bi-2-naphthol triflate.Tetrahedron Lett.,1990,31(44), 6321-6324.

Taisuke Hamada, et al. A novel photocatalytic asymmetric synthesis of (R)-(+)-1,1?-bi-2-naphthol derivatives by oxidative coupling of 3-substituted-2-naphthol with Δ-[Ru(menbpy)3]2+[menbpy = 4,4?-di(1R,2S,5R)-(-)-menthoxycarbonyl-2,2?-bipyridine], which posseses molecular helicity.J. Chem. Soc., Chem. Commun.,1993,11909-911.

GHS Hazard and Precautionary Statements

Hazard Statements: H301-H315-H319-H335

Toxic if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P280h-P305+P351+P338-P309-P310

Wear protective gloves/clothing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF exposed or if you feel unwell: Immediately call a POISON CENTER or doctor/physician.

Other References

Merck
14,1226
Beilstein
3616837
Hazard Class
6.1
Packing Group
III
Harmonized Tariff Code
2907.29
TSCA
No
RTECS
DU3106100

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