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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%

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

Dimensioni Prezzo ($) Quantità Disponibilità
1g 31,70
5g 89,70
25g 324,00
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(R)-(+)-1,1'-Bi(2-naphthol), 99%

MDL
MFCD00004068

Proprietà chimiche

Formula
C20H14O2
Peso formula
286.33
Punto di fusione
206-211°
Densità
1.301
Rotazione ottica
+34.5 (c=1 in THF)
Solubilità
Insoluble in water. Solubility in THF within almost transparency). Soluble in dioxane 50 mg/mL.

Applicazioni

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.

Note

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

Letteratura

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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H301-H315-H319-H335

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

Dichiarazioni precauzionali: P280h-P305+P351+P338-P309-P310a

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/doctor

Altri riferimenti

Merck
14,1226
Beilstein
3616837
Classe di rischio
6.1
Gruppo di imballaggio
III
Codice tariffe armonizzato
2907.29
TSCA
No
RTECS
DU3106100

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