60536-98-3

Usage

Uses

Used in Organic Synthesis:
2,2'-Dimethyl-1,1'-binaphthalene is used as a key intermediate in the synthesis of complex organic molecules for various applications. Its presence in the molecule allows for the formation of new chemical bonds and the creation of diverse structures, which can be further modified to achieve desired properties.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,2'-Dimethyl-1,1'-binaphthalene is used as a starting material for the development of new drugs. Its unique structure can be modified to create potential drug candidates with specific therapeutic properties, contributing to the discovery of novel treatments for various diseases.
Used in Chemical Research:
2,2'-Dimethyl-1,1'-binaphthalene is also utilized in chemical research to study the properties and reactivity of organic compounds. Its structure provides a platform for investigating various chemical reactions and mechanisms, furthering our understanding of organic chemistry and its applications.
Used in Material Science:
In the field of material science, 2,2'-Dimethyl-1,1'-binaphthalene can be employed as a component in the development of new materials with specific properties. Its incorporation into polymers or other materials can lead to the creation of materials with tailored characteristics, such as improved stability, solubility, or conductivity.

Upstream product

• 91-57-6 2-Methylnaphthalene 
• 36374-82-0 1-iodo-2-methylnaphthalene 
• 312303-50-7 2-(2-methyl-naphthalen-1-yl)-[1,3,2]dioxaborolane 
• 312303-48-3 4,4,5,5-tetramethyl-2-(2-methylnaphthalen-1-yl)-1,3,2-dioxaborolane 
• 1528-01-4 methyltributyltin 
• 86688-06-4 (R_a)-2,2'-diiodo-1,1'-binaphthyl 
• 21450-90-8 (2-methyl-1-naphthyl)magnesium bromide 
• 2586-62-1 1-bromo-2-methylnaphtalene 
• 103989-84-0 2-methyl-1-naphthylboronic acid 
• 5859-45-0 1-chloro-2-methylnaphthalene 
• 119906-95-5 4,5-dihydro-4,4-dimethyl-3H-dinaphtho<2,1-a:1',2'-e>stannepin 
• 75-16-1 methylmagnesium bromide 
• 141807-44-5 (+/-)-2,2'-bis(trifluoromethanesulfonyloxy)-1,1-binaphthyl 
• 1334420-88-0 C₁₆H₁₉BO₃ 

Downstream Products

• 155825-57-3 4-phenyl-4,5-dihydro-3H-dinaphtho<2,1-c;1',2'-e>phosphepine 
• 597579-92-5 rac-2,2'-bis[2,2-bis(4-dimethylaminophenyl)ethenyl]binaphthyl 
• 1312996-47-6 4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine-4-oxide 
• 96-76-4 2,4-di-tert-Butylphenol 
• 71031-40-8 2,2'-bis(diphenylphosphinylmethyl)-1,1'-binaphthyl 
• 865095-85-8 rac-2,2'-bis[2,2-bis(4-methoxyphenyl)ethenyl]binaphthyl 
• 515811-37-7 (S)-4-(4-methoxyphenyl)-4,5-dihydro-3H-dinaphtho[2,1-c;1',2'-e]phosphepine 
• 597579-95-8 rac-2,2'-bis[2,2-bis(4-dimethylaminophenyl)-2-hydroxyethyl]binaphthyl 

Relevant academic research and scientific papers

Application of a Ferrocene-Based Palladacycle Precatalyst to Enantioselective Aryl-Aryl Kumada Coupling

The palladium catalysed reaction of 1-iodo-2-methylnaphthalene and 2-methyl-1-naphthylmagnesium bromide gave quantitatively an (Sa)-configured cross-coupled product in 80 % e.e. using (R,Sp)-PPFA as a ligand. N,N-Dimethylaminomethylferrocene was cyclopalladated (Na2PdCl4, (S)?Ac?Phe?OH, 93 % e.e., as determined by 1H NMR as a result of self-induced non-equivalence), and the resulting (Sp)-configured dimeric palladacycle was employed as a precatalyst for this cross-coupling reaction (5 mol%). Addition to the palladacycle of diphenylphosphine and subsequent base-promoted bidentate ligand synthesis and palladium capture gave an in situ generated catalyst resulting in an (Sp)-configured product in up to 71 % e.e.

Supramolecular Polymerization of [5]Helicenes. Consequences of Self-Assembly on Configurational Stability

The supramolecular polymerization of [5]helicenes 1 and 2 is investigated. The self-assembly of these helicenes proceeds by the operation of H-bonding interactions with a negligible participation of π-stacking. The enantiopurity of the sample has a dramatic effect on the supramolecular polymerization mechanism since it reverts the isodesmic mechanism for the racemic mixture to a cooperative one for the enantioenriched sample. Noticeably, the formation of supramolecular polymers efficiently increases the configurational stability of 1,14-unsubstituted [5]helicenes.

NOVEL CHIRAL DIHYDROBENZOAZAPHOSPHOLE LIGANDS AND SYNTHESIS THEREOF

This invention relates to novel phosphorous ligands useful for organic transformations. Methods of making and using the ligands in organic synthesis are described. The invention also relates to processes for preparing the novel ligands.

Computationally Assisted Mechanistic Investigation and Development of Pd-Catalyzed Asymmetric Suzuki-Miyaura and Negishi Cross-Coupling Reactions for Tetra- ortho-Substituted Biaryl Synthesis

Metal-catalyzed cross-coupling reactions are extensively employed in both academia and industry for the synthesis of biaryl derivatives for applications to both medicine and material science. Application of these methods to prepare tetra-ortho-substituted

A Binaphthyl-Based Scaffold for a Chiral Dirhodium(II) Biscarboxylate Ligand with α-Quaternary Carbon Centers

A chiral dirhodium(II) paddlewheel complex has been synthesized from biscarboxylate ligands derived from BINOL, and the resulting complex has been used in enantioselective carbene/alkyne cascade reactions. The ligand design was guided by requirements of α

Readily available catalysts for demanding Suzuki–Miyaura couplings under mild conditions

A straightforward synthesis of a sterically hindered and electron rich bidentate monophosphine biaryl ligand Sym-Phos of C,P-type of complexation was realised in a high yield starting from simple substrates in easily affordable conditions. In combination with a palladium source, the obtained ligand formed a highly active catalyst mediating sterically demanding Suzuki–Miyaura coupling reactions in aqueous media even at 60 °C and with no need to protect the reaction mixture by an inert gas.

Dimerization of Aryl Sulfonates by in situ Generated Nickel(0)

A mild and user-friendly nickel-catalyzed method for the reductive homocoupling of aromatic tosylates is presented. The reaction proceeds between room temperature and 60 °C, with stable substrates (ArOTs) easily prepared from inexpensive and commercially available phenols or naphthols. It relies on a catalytic amount (10 mol%) of a robust catalyst (NiBr2bipy) that does not require the preparation of sensitive organometallic intermediates. Yields are good to excellent.

2: A highly hindered pre-catalyst for the synthesis of tetra-ortho-substituted biaryls via Grignard reagent cross-coupling

The new well-defined catalyst [Pd(μ-Cl)Cl(IPr*)]2 enables the efficient Grignard reagent cross-coupling for the synthesis of tetra-ortho-substituted biaryls. The high reactivity of the complex is associated with the important bulkiness of the I

Synthesis of axially chiral 1,1′-binaphthalenes by palladium-catalysed cross-coupling reactions of triorganoindium reagents

1,1′-Binaphthalenes and heterocyclic analogues can be efficiently prepared by palladium-catalysed cross-coupling reactions between tri(1-naphthyl)indium reagents and 1-halonaphthalenes and haloisoquinolines. The reactions were usually carried out in THF at 80 °C with a slight excess of the indium reagent (40 mol-%) and a low catalyst loading (4 mol-% Pd) to afford the cross-coupling products in good yields (45-99 %). The method allows the synthesis of sterically hindered 2-substituted and 2,2′-disubstituted 1,1′-binaphthalenes and naphthylisoquinolines. In addition, the coupling reactions can be performed enantioselectively and the best enantiomeric excesses were obtained by using the chiral amino-phosphane ferrocenyl ligand (R,S)-PPFA. 1,1′-Binaphthalenes and heterocyclic derivatives have been synthesized by palladium-catalysed cross-coupling reactions between tri(1-naphthyl)indium reagents and 1-halonaphthalenes and haloisoquinolines, including 2-substituted and 2,2′-disubstituted 1,1′-binaphthyls. The coupling reactions can be performed enantioselectively in the presence of the chiral ligand (R,S)-PPFA. Copyright

Large yet flexible N-heterocyclic carbene ligands for palladium catalysis

A straightforward and scalable eight-step synthesis of new N-heterocyclic carbenes (NHCs) has been developed from inexpensive and readily available 2-nitro-m-xylene. This process allows for the preparation of a novel class of NHCs coined ITent ("Tent" for "tentacular") of which the well-known IMes (N,N′-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene), IPr (N,N′-bis(2,6-di(2-propyl)phenyl)imidazol-2-ylidene) and IPent (N,N′-bis(2,6-di(3-pentyl)phenyl)imidazol-2-ylidene) NHCs are the simplest and already known congeners. The synthetic route was successfully used for the preparation of three members of the ITent family: IPent (N,N′-bis(2,6- di(3-pentyl)phenyl)imidazol-2-ylidene), IHept (N,N′-bis(2,6-di(4-heptyl) phenyl)imidazol-2-ylidene) and INon (N,N′-bis(2,6-di(5-nonyl)phenyl) imidazol-2-ylidene). The electronic and steric properties of each NHC were studied through the preparation of both nickel and palladium complexes. Finally the effect of these new ITent ligands in Pd-catalyzed Suzuki-Miyaura and Buchwald-Hartwig cross-couplings was investigated. Tentacular NHCs: A straightforward, scalable eight-step synthesis of N-heterocyclic carbenes (NHCs) has been developed using inexpensive and readily available 2-nitro-m-xylene, allowing the preparation of a class of NHCs designated ITent ("Tent" for "tentacular"). The electronic and steric properties of each NHC were studied through the preparation of both nickel and palladium complexes, and the effect of these new ITent ligands in Pd-catalyzed Suzuki-Miyaura and Buchwald-Hartwig cross-couplings was investigated.