32587-64-7

Usage

Uses

Used in Chemical Production:
2,2'-DIMETHYLBIPHENYL is used as a key component in the production of polycarbonate and epoxy resins, which are essential materials in the manufacturing of a wide range of products, from plastics to protective coatings.
Used in Dye and Pigment Manufacturing:
2,2'-DIMETHYLBIPHENYL is utilized as a precursor in the creation of dyes and pigments, contributing to the coloration of various products in different industries.
Used in Household Product Formulation:
2,2'-DIMETHYLBIPHENYL is found in some household products, such as adhesives and sealants, where its adhesive properties are beneficial for bonding materials together.
Used in Rubber and Plastics Manufacturing:
As a solvent, 2,2'-DIMETHYLBIPHENYL is employed in the manufacturing process of rubber and plastics, aiding in the formation and shaping of these materials.
Safety Considerations:
When working with 2,2'-DIMETHYLBIPHENYL, it is crucial to adhere to safety precautions due to its flammability and the potential for releasing harmful vapors, ensuring a secure and healthy work environment.

Upstream product

• 2586-62-1 1-bromo-2-methylnaphtalene 
• 21450-90-8 (2-methyl-1-naphthyl)magnesium bromide 
• 91-57-6 2-Methylnaphthalene 
• 917-64-6 methyl magnesium iodide 
• 141807-44-5 (+/-)-2,2'-bis(trifluoromethanesulfonyloxy)-1,1-binaphthyl 
• 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 
• 823-96-1 Trimethylboroxine 
• 86688-06-4 (R_a)-2,2'-diiodo-1,1'-binaphthyl 
• 1528-01-4 methyltributyltin 
• 80991-26-0 (R)-(-)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]oxepine 
• 74-88-4 methyl iodide 
• 103989-84-0 2-methyl-1-naphthylboronic acid 

Downstream Products

• 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 
• 155825-57-3 4-phenyl-4,5-dihydro-3H-dinaphtho<2,1-c;1',2'-e>phosphepine 

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.

Enantioselective cross-coupling for axially chiral tetra-ortho-substituted biaryls and asymmetric synthesis of gossypol

The axially chiral tetra-ortho-substituted biaryl skeleton exists in numerous biologically important natural products, pharmaceutical molecules, chiral catalysts, and ligands. The efficient synthesis of chiral tetra-ortho-substituted biaryl structures rem

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

Synthesis and catalytic activity of chiral dicarbene dipalladium complexes incorporating the S-binaphthol unit

A series of chiral di-N-heterocyclic carbene (NHC) dipalladium complexes, [{PdPyCl2}2(di-NHC)], in which di-NHC represents a diimidazolylidene, featuring an (S)-3,3'-dimethyl-2,2'-dimethoxy-1,1'-binaphthalene spacer between the carbene units, have been prepared. The influence of ligand size on the catalytic activity of these complexes in the Suzuki reaction of phenylboronic acid with p-bromotoluene has been investigated. The most sterically hindered complex, bearing the di-isopropylphenyl group, showed the greatest catalytic activity, and it is active for various aryl halides with different electronic and steric properties.

Palladium-Catalyzed Asymmetric Suzuki-Miyaura Cross Coupling with Homochiral Phosphine Ligands Having Tetrahydro-1 H -imidazo[1,5-a ]indole Backbone

Amphiphilic polystyrene-poly(ethylene glycol) resin-supported chiral imidazoindole phosphines (PS-PEG-L?), (3R,9aS)-2-aryl-3-(2-dialkylphosphino)phenyltetrahydro-1H-imidazo[1,5-a]indol-1-one, bearing PPh2, P(t-Bu)2, and P(c-Hex)2 groups were designed and prepared with a view toward using them in aqueous heterogeneous asymmetric Suzuki-Miyaura biaryl coupling. The asymmetric coupling of 2-substituted 1-iodonaphthalenes and 2-substituted naphthalen-1-ylboronic acid took place in water under heterogeneous conditions in the presence of 10 mol% palladium of PS-PEG-L?-Pd complexes to give up to 94% ee of (S)-2,2′-disubstituted 1,1′-binaphthyls.

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.

Development of chiral bis-hydrazone ligands for the enantioselective cross-coupling reactions of aryldimethylsilanolates

A palladium-catalyzed, enantioselective, aryl-aryl cross-coupling reaction using 1-naphthyldimethylsilanolates and chiral bis-hydrazone ligands has been developed. A family of glyoxal bis-hydrazone ligands containing various 2,5-diarylpyrrolidine groups was prepared to evaluate the influence of ligand structure on the rate and enantioselectivity of the cross-coupling. New synthetic routes to the 1-amino-2,5-diarylpyrrolidines were developed to enable the structure/reactivity-selectivity studies. Role reversal experiments of aryldimethylsilanolates and aryl bromides result in biaryl products with the same configuration and similar enantioselectivities implying that reductive elimination is the stereodetermining step. The origin of stereoselectivity is rationalized through computational modeling of diarylpalldium(II) complex which occurs through a conrotatory motion for the two aryl groups undergoing C-C bond formation.