117745-41-2

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General Description

1,1'-Binaphthalene, 6,6'-dibromo-2,2'-dimethoxy-, (1S)-, also known as (S)-(-)-6,6'-dibromo-2,2'-dimethoxy-1,1'-binaphthyl, is an organic compound with the chemical formula C24H18Br2O2. It is a chiral compound, meaning it has a non-superimposable mirror image, and it is commonly used as a chiral ligand in asymmetric synthesis and catalysis. 1,1'-Binaphthalene, 6,6'-dibromo-2,2'-dimethoxy-, (1S)- is often used in the field of organic chemistry to promote highly enantioselective reactions. It has been used as a precursor for the synthesis of other chiral compounds and for the development of new catalytic processes. Overall, 1,1'-Binaphthalene, 6,6'-dibromo-2,2'-dimethoxy-, (1S)- is a valuable chemical in the advancement of asymmetric synthesis and catalysis in organic chemistry.

Upstream product

• 79082-80-7 (S)-6,6'-dibromo-1,1'-binaphthalene-2,2'-diol 
• 77-78-1 dimethyl sulfate 
• 5111-65-9 2-Bromo-6-methoxynaphthalene 
• 15231-91-1 6-bromo-naphthalen-2-ol 
• 602-09-5 1,1'-bi-2-naphthol 
• 75685-01-7 2,2'-dimethoxy-1,1'-binaphthyl 
• 74-88-4 methyl iodide 

Relevant academic research and scientific papers

Chromophoric binaphthyl derivatives

(Chemical Equation Presented) A short synthetic route is outlined, starting from bromo-BN derivatives, via halogen lithium exchange, subsequent Michael reaction with dimethylaminoacrolein, hydrolysis to the corresponding aldehyde, and final condensation with a benzothiazolium unit to produce a BN-pentamethinium system, which absorbs in the visible range around 450 nm. Enantiopure ligands show a decent Cotton effect in the CD spectrum. Preliminary data show potential of these compounds in the area of supramolecular chemistry (enantioselective recognition) and also for medicinal application (induction of apoptosis).

Novel π-expanded chrysene-based axially chiral molecules: 1,1′-bichrysene-2,2′-diols and thiophene analogs

1,1′-Bichrysene-2,2′-diol and its thiophene analogs, 6,6′-biphenanthro-[1,2-b]thiophene-7,7′-diols, as a series of novel π-expanded chrysene-/phenanthro[1,2-b]thiophene-based axially chiral molecules are synthesized from 1,1′-bi-2-naphthols with key steps

Molecular design to enhance binaphthyl-based chiroptics using organoboron chemistry in isomeric chiral scaffolds

Access to high-performance circularly polarized luminescence is highly desired in materials science but it hitherto remains a considerable challenge. We herein present a conceptually universal design strategy to improve the chiral luminescent properties of a series of binaphthyl-based compounds (MeBTT, MeBTB, p-BTT, p-BTB, m-BTT and m-BTB). The binaphthyl skeleton in all cases was π-functionalized either by an electron donor (Ar3N) or acceptor (Ar3B), and correlations of the molecular structures to their photophysical characters were systematically investigated. They all exhibited strong photoluminescence both in solution with quantum efficiency (ΦPL,DCM) up to 100% and as solids (ΦPL,solid = 21-59%). The optical resolution into enantiomers via chiral HPLC was achieved for p-BTT, p-BTB, m-BTT and m-BTB with helically ring-structured binaphthyls. We further unveiled that the sterically more constrained m-BTT and m-BTB exhibit superior chiroptical properties in circularly polarized luminescence (CPL) relative to the isomers p-BTT and p-BTB, evident from the order of magnitude of luminescence dissymmetry factor (|glum|) increasing from 10-4 to 10-3 in solution. Moreover, the double functionalization of the binaphthyl moiety with an electron donor-acceptor charge-transfer system resulted also in an experimentally improved CPL activity, as rationalized by TD-DFT calculations of a key angle (θμ,m) between vectors of the electric and magnetic transition dipole moments in the excited states. The three organoboranes (MeBTB, p-BTB and m-BTB) displayed dual emissions in polar solvents and the low-energy charge transfer bands were demonstrated to be air-sensitive and thermally responsive at elevated temperature. This journal is

New compound and a manufacturing method thereof and a like annular crown ether binaphthayl group having the structure

PROBLEM TO BE SOLVED: To provide a novel compound including a crown ether-like structure and an optically active binaphthyl group which is expected in the application as an asymmetry recognizing agent and in various applications as various functional materials and to provide a manufacturing method thereof. SOLUTION: The novel compound having a crown ether-like structure and a binaphthyl structure is provided by further derivatizing a binaphthyl derivative in which the 6,6'-positions are replaced with bromines and the 3,3'-positions are replaced with specific substituents, by a specific reaction. COPYRIGHT: (C)2013,JPOandINPIT

Efficient oxidative biaryl coupling reaction of phenol ether derivatives using hypervalent iodine(III) reagents

Oxidative biaryl coupling reaction of phenol ether derivatives with the hypervalent iodine reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA), in the presence of BF3·Et2O gave a variety of substituted biphenyl and binaphthyl compounds in high yields. Replacement of PIFA with a more practical polymer-supported hypervalent iodine reagent has also been achieved.

Thallium in Organic Synthesis. 58. Regiospecific Intermolecular Oxidative Dehydrodimerization of Aromatic Compounds to Biaryls Using Thallium (III) Trifluoroacetate

Treatment of a variety of aromatic substrates with thallium(III) trifluoroacetate (TTFA) in trifluoroacetic acid (TFA), or in carbon tetrachloride or acetonitrile containing boron trifluoride etherate, results in smooth, rapid, and direct regiospecific oxidative dehydrodimerization to give symmetrical biaryls in good to excellent yield.The method is particularly useful when applied to substrates in which the ring substituents are either electron donating or mildly electron withdrawing.Aromatic substrates which contain powerful electron-withdrawing groups (CN, COOR, NO2) fail to react.The reaction is postulated to proceed via (a) reaction of TTFA with the aromatic substrate and generation of the radical cation Ar+; (b) reaction of this electrophile with the aromatic substrate; (c) oxidative aromatization of the intermediate thus produced by TTFA.Biaryls can be obtained similarly by oxidation of the same substrates with either mercury(II) trifluoroacetate in TFA containing boron trifluoride, lead(IV) acetate in acetonitrile containing boron trifluoride, iron(III) chloride in methylene chloride, or cobalt(III) fluoride in TFA.Yields in the Hg(II) and Fe(III) reactions are generally inferior to those obtained with TTFA, but those obtained in the Pb(IV) and Co(III) oxidations are in many instances comparable to, or even better than, the TTFA results.The oxidations with Hg(II), Pb(IV), Fe(III), and CO(III) are also postulated to proceed via a radical cation mechanism.