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Thermo Scientific Chemicals
(R)-(+)-1,1'-Bi(2-naphthol), 99%
CAS: 18531-94-7 | C20H14O2 | 286.33 g/mol
化学物質識別子
CAS18531-94-7
IUPAC Name[1,1'-binaphthalene]-2,2'-diol
Molecular FormulaC20H14O2
InChI KeyPPTXVXKCQZKFBN-UHFFFAOYSA-N
SMILESOC1=CC=C2C=CC=CC2=C1C1=C(O)C=CC2=CC=CC=C12
さらに表示
仕様
スペックシート
スペックシートAppearance (Color)White to cream or pale gray
FormCrystals or powder or crystalline powder
Melting Point (clear melt)205-212°C
Optical Rotation+35.5° ± 2° (c=1 in THF)
Assay (HPLC)≥98.5%
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.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
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.
Solubility
Insoluble in water. Solubility in THF within almost transparency). Soluble in dioxane 50 mg/mL.
Notes
Store away from oxidizing agents. Keep the container tightly closed and place it in a cool, dry and well ventilated condition.
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.
Solubility
Insoluble in water. Solubility in THF within almost transparency). Soluble in dioxane 50 mg/mL.
Notes
Store away from oxidizing agents. Keep the container tightly closed and place it in a cool, dry and well ventilated condition.
RUO – Research Use Only
General 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.