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

Description

CAS: 18531-94-7 | C20H14O2 | 286.33 g/mol

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.

Specifications

Chemical Identifiers

• CAS: 18531-94-7
• Molecular Formula: C20H14O2
• Molecular Weight (g/mol): 286.33
• MDL Number: MFCD00004068
• InChI Key: PPTXVXKCQZKFBN-UHFFFAOYSA-N
• Synonym: 1,1'-bi-2-naphthol, s---1,1'-bi-2-naphthol, r-+-1,1'-bi-2-naphthol, 1,1'-binaphthalene-2,2'-diol, binol, 1,1'-binaphthyl-2,2'-diol, 2,2'-dinaphthol, beta-binaphthol, r-1,1'-bi-2-naphthol, s-1,1'-binaphthalene-2,2'-diol
• PubChem CID: 11762
• IUPAC Name: 1-(2-hydroxynaphthalen-1-yl)naphthalen-2-ol
• SMILES: C1=CC=C2C(=C1)C=CC(=C2C3=C(C=CC4=CC=CC=C43)O)O

• Melting Point: 206°C to 211°C
• Density: 1.301
• Odor: Characteristic
• Quantity: 1 g
• UN Number: UN2811
• Beilstein: 3616837
• Merck Index: 14,1226
• Solubility Information: Insoluble in water. Solubility in THF within almost transparency). Soluble in dioxane 50mg/mL.
• Optical Rotation: +34.5 (c=1 in THF)
• Formula Weight: 286.33
• Percent Purity: 99%
• Chemical Name or Material: (R)-(+)-1,1'-Bi(2-naphthol)

Safety and Handling

Hazard Category	H301-H315-H319-H335
Hazard Statement	GHS H Statement H301-H315-H319-H335 Toxic if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statement	P261-P264b-P270-P271-P280-P301+P310-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P362-P501c
DOTInformation	Transport Hazard Class: 6.1; Packing Group: III; Proper Shipping Name: TOXIC SOLIDS, ORGANIC, N.O.S.
RTECSNumber	DU3106100
TSCA	No
Recommended Storage	Ambient temperatures

SDS

RUO – Research Use Only