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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.

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  • 287111-93-7 Structure
  • Basic information

    1. Product Name: R-3,3'-diiodo-[1,1'-Binaphthalene]-2,2'-diol
    2. Synonyms: R-3,3'-diiodo-[1,1'-Binaphthalene]-2,2'-diol
    3. CAS NO:287111-93-7
    4. Molecular Formula: C20H12I2O2
    5. Molecular Weight: 538.11702
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 287111-93-7.mol
  • Chemical Properties

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

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 287111-93-7(Hazardous Substances Data)

287111-93-7 Usage

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.

Check Digit Verification of cas no

The CAS Registry Mumber 287111-93-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,8,7,1,1 and 1 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 287111-93:
(8*2)+(7*8)+(6*7)+(5*1)+(4*1)+(3*1)+(2*9)+(1*3)=147
147 % 10 = 7
So 287111-93-7 is a valid CAS Registry Number.

287111-93-7Relevant articles and documents

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

Wirth, Thomas,Zhang, Huaiyuan

, (2022/03/17)

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.

Aggregation-induced CPL response from chiral binaphthyl-based AIE-active polymers via supramolecular self-assembled helical nanowires

Ma, Jing,Wang, Yuxiang,Li, Xiaojing,Yang, Lan,Quan, Yiwu,Cheng, Yixiang

, p. 184 - 189 (2018/04/14)

In this paper chiral polymer R-P could be synthesized by click polymerization reaction of (R)-3,3′-diethynyl-2,2′-bis(octyloxy)-1,1′-binaphthalene (R-M-1) and 1,2-bis(4-azidophenyl)-1,2-diphenylethene (M-2), and S-P was obtained by click polymerization re

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

Meng, Fandian,Li, Fei,Yang, Lan,Wang, Yuxiang,Quan, Yiwu,Cheng, Yixiang

, p. 1282 - 1288 (2018/04/14)

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.

Doping-free circularly polarized electroluminescence of AIE-active chiral binaphthyl-based polymers

Yang, Lan,Zhang, Yu,Zhang, Xueyan,Li, Nengquan,Quan, Yiwu,Cheng, Yixiang

supporting information, p. 9663 - 9666 (2018/09/10)

AIE-active chiral polymer enantiomers (S-/R-P) can emit green circularly polarized electroluminescence (CP-EL) with gEL up to 0.024 without alignment layers and chiral dopants, which represents the first example of CP-OLEDs based on AIE-active

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

Meesala, Yedukondalu,Wu, Hsyueh-Liang,Koteswararao, Bommisetti,Kuo, Ting-Shen,Lee, Way-Zen

, p. 4385 - 4393 (2015/04/16)

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.

Enantioenriched synthesis of C 1-symmetric BINOLs: Iron-catalyzed cross-coupling of 2-naphthols and some mechanistic insight

Egami, Hiromichi,Matsumoto, Kenji,Oguma, Takuya,Kunisu, Takashi,Katsuki, Tsutomu

supporting information; experimental part, p. 13633 - 13635 (2010/11/17)

Highly enantioselective aerobic oxidative cross-coupling of 2-naphthols with broad substrate scope was achieved using an iron(salan) complex as the catalyst. Enantiomeric excesses of the products ranged from 87 to 95%. The scope of the cross-coupling reac

Chiral metallacyclophanes: Self-assembly, characterization, and application in asymmetric catalysis

Hua, Jiang,Lin, Wenbin

, p. 861 - 864 (2007/10/03)

(Equation presented) A family of chiral metallacyclophanes has been readily assembled based on robust Pt-acetylide linkage and characterized by a variety of spectroscopic techniques and X-ray crystallography. The steric congestion around the chiral dihydr

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