287111-93-7

Basic information

• Product Name: R-3,3'-diiodo-[1,1'-Binaphthalene]-2,2'-diol
• Synonyms: R-3,3'-diiodo-[1,1'-Binaphthalene]-2,2'-diol
• CAS NO: 287111-93-7
• Molecular Formula: C20H12I2O2
• Molecular Weight: 538.11702
• Mol File: 287111-93-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 312-314 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• Boiling Point: 491.7±45.0 °C(Predicted)
• Appearance: /
• Density: 2.038±0.06 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 6.54±0.50(Predicted)
• CAS DataBase Reference: R-3,3'-diiodo-[1,1'-Binaphthalene]-2,2'-diol(CAS DataBase Reference)
• NIST Chemistry Reference: R-3,3'-diiodo-[1,1'-Binaphthalene]-2,2'-diol(287111-93-7)
• EPA Substance Registry System: R-3,3'-diiodo-[1,1'-Binaphthalene]-2,2'-diol(287111-93-7)

Safety Data

• Hazardous Substances Data: 287111-93-7(Hazardous Substances Data)

Usage

Description

R-3,3'-diiodo-[1,1'-Binaphthalene]-2,2'-diol is a chemical compound with the molecular formula C20H14I2O2. It is a derivative of binaphthol, a versatile chiral building block widely used in asymmetric synthesis. R-3,3'-diiodo-[1,1'-Binaphthalene]-2,2'-diol is known for its important role as a chiral ligand in various catalytic reactions, particularly in asymmetric catalysis. Its unique structure and properties make it an important tool in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals. Additionally, the presence of iodine atoms in the molecule contributes to its reactivity and potential applications in chemical transformations. Overall, R-3,3'-diiodo-[1,1'-Binaphthalene]-2,2'-diol is a valuable compound with diverse applications in organic synthesis and catalysis.

Uses

Used in Pharmaceutical Industry:
R-3,3'-diiodo-[1,1'-Binaphthalene]-2,2'-diol is used as a chiral ligand for asymmetric catalysis in the synthesis of pharmaceuticals. Its unique structure allows for the creation of enantioselective catalysts, which are essential for producing single-enantiomer drugs with desired biological activity and reduced side effects.
Used in Agrochemical Industry:
In the agrochemical industry, R-3,3'-diiodo-[1,1'-Binaphthalene]-2,2'-diol is utilized as a chiral ligand in the development of enantioselective catalysts for the synthesis of agrochemicals. This helps in producing enantiomerically pure active ingredients, which can improve the effectiveness and safety of these chemicals.
Used in Fine Chemicals Synthesis:
R-3,3'-diiodo-[1,1'-Binaphthalene]-2,2'-diol is employed as a chiral building block and ligand in the synthesis of various fine chemicals. Its unique properties enable the production of enantiomerically pure compounds, which are crucial for applications in fragrances, flavors, and other specialty chemicals.
Used in Chemical Transformations:
Due to the presence of iodine atoms, R-3,3'-diiodo-[1,1'-Binaphthalene]-2,2'-diol is used in chemical transformations to enhance reactivity and facilitate specific reaction pathways. This makes it a valuable tool in organic synthesis for the development of new compounds and materials.

Upstream product

• 394737-28-1 (±)?3,3'?diiodo?2,2'?dimethoxy?1,1'?binaphthalene 
• 103027-41-4 1-(tert-butyldimethylsilyl)-4-(4',4',5',5'-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-5-ol 
• 17295-11-3 methyl 6-hydroxynaphthalene-2-carboxylate 
• 173831-50-0 rac-2,2'-bis-(methoxymethoxy)-1,1'-binaphthalene 
• 142010-88-6 (rac)-3,3’-diiodo-2,2’-di(methoxymethoxy)-1,1’-binaphthyl 
• 602-09-5 1,1'-bi-2-naphthol 
• 75685-01-7 2,2'-dimethoxy-1,1'-binaphthyl 

Downstream Products

• 39215-21-9 [1,1'-binaphthalene]-2,2',3,3'-tetraol 

Relevant articles and documents

Oxidation of BINOLs by Hypervalent Iodine Reagents: Facile Synthesis of Xanthenes and Lactones

Xanthene derivatives have broad applications in medicines, fluorescent probes, dyes, food additives, etc. Therefore, much attention was focused on developing the synthetic methods to prepare these compounds. Binaphthyl-based xanthene derivatives were prepared through the oxidation of BINOLs promoted by the hypervalent iodine reagent iodosylbenzene (PhIO). Nine-membered lactones were obtained through a similar oxidative reaction when iodoxybenzene (PhIO2) was used. Additionally, one-pot reactions of BINOLs, PhIO and nucleophiles such as alcohols and amines were also investigated to provide alkoxylated products and amides in good to excellent yields.

The amplified circularly polarized luminescence emission response of chiral 1,1′-binaphthol-based polymers via Zn(II)-coordination fluorescence enhancement

Two kinds of chiral 1,1′-binaphthol (BINOL)-based polymer enantiomers were designed and synthesized by the polymerization of 5,5′-((2,2′-bis (octyloxy)-[1,1′-binaphthalene]-3,3′-diyl)bis(ethyne-2,1-diyl))bis(2-hydroxybenzaldehyde) (M1) with alkyl diamine (M2) via nucleophilic addition–elimination reaction. The resulting chiral polymers can exhibit mirror image cotton effects either in the absence or in the presence of Zn2+ ion. Almost no fluorescence or circularly polarized luminescence (CPL) emission could be observed for two chiral BINOL-based polymer enantiomers in the absence of Zn2+. Interestingly, the chiral polymers can show strong fluorescence and CPL response signals upon the addition of Zn2+, which can be attributed to Zn2+-coordination fluorescence enhancement effect. This work can develop a new strategy on the design of the novel CPL materials via metal-coordination reaction.

Aerobic oxidative coupling of 2-naphthol derivatives catalyzed by a hexanuclear bis(μ-hydroxo)copper(II) catalyst

A novel hexanuclear bis(μ-hydroxo)copper(II) complex, [L3(Cu2(μ-OH)2)3](ClO4)6 (1), was synthesized with dinucleating ligand N,N,N,N-tetra(pyridin-2-ylmethyl)-m-xylene diamine (L). Complex 1 is fully characterized by X-ray crystallography and magnetic susceptibility in the solid state and UV-vis and electron paramagnetic resonance spectroscopy in solution. The molecular structure of 1 possesses three dicopper cores, in which two copper centers are bridged by two hydroxide groups and separated by a distance ranging from 2.8852(15) to 2.8937(10) ?. In addition, the three dicopper cores are linked by the dinucleating ligand between each pair of adjacent dicopper cores. Importantly, aerobic oxidative coupling of 2,4-di-tert-butylphenol, 2-naphthol, and six 2-naphthol derivatives was achieved in 33-96% yield using complex 1 as a catalyst.