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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%

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

Dimensions Prix ($) Quantité Disponibilité
1g 32,96
5g 93,32
25g 294,30
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(R)-(+)-1,1'-Bi(2-naphthol), 99%

MDL
MFCD00004068

Propriétés chimiques

Formule
C20H14O2
Poids formulaire
286.33
Point de fusion
206-211°
Densité
1.301
Pouvoir rotatoire
+34.5 (c=1 in THF)
Solubilité
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.

Références bibliographiques

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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H301-H315-H319-H335

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

Mentions de prudence: 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.

Autres références

Merck
14,1226
Beilstein
3616837
Classe de danger
6.1
Groupe d'emballage
III
Code tarifaire harmonisé
2907.29
TSCA
No
RTECS
DU3106100

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