265116-85-6

Basic information

• Product Name: 3,3''-[OXYBIS(METHYLENE)]BIS-(1R,1''R)-1,1''-BI-2-NAPHTHOL
• Synonyms: 3,3''-[OXYBIS(METHYLENE)]BIS-(1R,1''R)-1,1''-BI-2-NAPHTHOL;(1R,1''R)-3,3''-[oxybis(methylene)]bis-[1,1'-Binaphthalene]-2,2'-diol;3,3'-[Oxybis(methylene)]bis(1,1'-binaphthalene-2,2'-diol);(1R,1''R)-3,3''-[Oxybis(methylene)]bis-[1,1'-binaphthalene] -2,2'-diol, 99%e.e.
• CAS NO: 265116-85-6
• Molecular Formula: C42H30O5
• Molecular Weight: 614.68
• Mol File: 265116-85-6.mol

Chemical Properties

• Boiling Point: 766.8±55.0 °C(Predicted)
• Appearance: /
• Density: 1.365±0.06 g/cm3(Predicted)
• PKA: 8.19±0.50(Predicted)
• CAS DataBase Reference: 3,3''-[OXYBIS(METHYLENE)]BIS-(1R,1''R)-1,1''-BI-2-NAPHTHOL(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3''-[OXYBIS(METHYLENE)]BIS-(1R,1''R)-1,1''-BI-2-NAPHTHOL(265116-85-6)
• EPA Substance Registry System: 3,3''-[OXYBIS(METHYLENE)]BIS-(1R,1''R)-1,1''-BI-2-NAPHTHOL(265116-85-6)

Safety Data

• Hazardous Substances Data: 265116-85-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
3,3''-[Oxybis(methylene)]bis-(1R,1''R)-1,1''-bi-2-naphthol is used as a chiral ligand in the pharmaceutical industry for its ability to enhance enantioselectivity in catalytic asymmetric epoxidation reactions. This property is crucial for the production of enantiomerically pure compounds, which are essential in the development of effective and safe medications.
Used in Photonic Materials:
In the field of photonic materials, 3,3''-[Oxybis(methylene)]bis-(1R,1''R)-1,1''-bi-2-naphthol is utilized for its potential to contribute to the development of advanced optical devices. Its unique molecular structure allows for specific interactions and properties that can be harnessed in the creation of materials with tailored optical characteristics.
Used in Polymer Science:
3,3''-[Oxybis(methylene)]bis-(1R,1''R)-1,1''-bi-2-naphthol is employed as a component in polymer science to explore its role in the synthesis of new polymeric materials. Its chiral nature and structural features may lead to the development of polymers with specific properties, such as improved mechanical strength, thermal stability, or responsiveness to external stimuli.

Upstream product

• 265116-89-0 C₅₀H₄₆O₉ 
• 173831-50-0 rac-2,2'-bis-(methoxymethoxy)-1,1'-binaphthalene 
• 173961-76-7 3-hydroxymethyl-2,2'-bis(methoxymethyloxy)-1,1'-binaphthalene 
• 349149-07-1 (S)/(R)-1,1'-binaphthalene-2,2-bis(methoxymethyloxy)-3-carbaldehyde 
• 503588-40-7 3-bromomethyl-2,2'-bis(methoxymethyloxy)-1,1'-binaphthalene 
• 865444-97-9 methanesulfonic acid 2,2'-bis-methoxymethoxy-[1,1']binaphthalenyl-3-ylmethyl ester 
• 602-09-5 1,1'-bi-2-naphthol 
• 265116-89-0 C₅₀H₄₆O₉ 

Downstream Products

• 321837-08-5 La(C₁₀H₅OC₁₀H₆O)(C₁₀H₅OC₁₀H₆OH)(CH₂)2O 

Relevant articles and documents

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Catalytic enantioselective meso-epoxide ring opening reaction with phenolic oxygen nucleophile promoted by gallium heterobimetallic multifunctional complexes

The catalytic enantioselective meso-epoxide ring opening reaction with phenolic oxygen nucleophile (4-methoxyphenol) is described for the first time herein. This reaction was first found to be promoted by (R)-GaLB (Ga = gallium, L = lithium, B = (R)-BINOL), giving a variety of epoxide opening products in good to high ee (67-93% ee). However, chemical yield was only modest (yield 31-75%), despite the use of more than 20 mol % GaLB. This was due to the undesired ligand exchange between BINOL and 4-methoxyphenol, which resulted in the decomplexation of GaLB. Application of various known chiral ligands such as 6,6'-bis((triethylsilyl)ethynyl)-BINOL and H8-BINOL were examined, but satisfactory results were not obtained. To overcome this problem a novel linked-BINOL containing coordinative oxygen atom in the linker has been developed. By linking two BINOL units in GaLB, the stability of the Ga-complex was greatly improved. Using 3-10 mol % (R,R)-Ga-Li-linked- BINOL complex, a variety of epoxide opening reactions were found to proceed smoothly, affording products in analogous ee (66-96% ee) and in much higher yield (yield 67-94%) compared to (R)-GaLB. The structure of the LiCl free Ga- Li-linked-BINOL complex was elucidated by X-ray analysis. This is the first X-ray data for an asymmetric catalyst containing gallium. The possible mechanism of the entitled reaction is also discussed, based on the X-ray structure of the Ga-complex.