32587-64-7

Basic information

• Product Name: 2,2'-DIMETHYLBIPHENYL
• Synonyms: (S)-2,2'-DIMETHYL-1,1'-BINAPHTHYL;O,O'-BITOLUENE;O,O'-BITOLYL;(R)-2,2'-DIMETHYL-1,1'-BINAPHTHYL;2,2'-DIMETHYLBIPHENYL;2,2'-BITOLYL;S-2,2'-DiMethyl-1,1'-binaphthalene;(S)-2,2'-Dimethyl-1,1'-binaphthyl
• CAS NO: 32587-64-7
• Molecular Formula: C₂₂H₁₈
• Molecular Weight: 182.26
• Mol File: 32587-64-7.mol
• Article Data: 64

Chemical Properties

• Melting Point: 72-74℃ (methanol )
• Boiling Point: 401.8 °C at 760 mmHg
• Flash Point: >230 °F
• Appearance: /
• Density: 0.989 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.5745(lit.)
• CAS DataBase Reference: 2,2'-DIMETHYLBIPHENYL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-DIMETHYLBIPHENYL(32587-64-7)
• EPA Substance Registry System: 2,2'-DIMETHYLBIPHENYL(32587-64-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 32587-64-7(Hazardous Substances Data)

Usage

General Description

2,2'-DIMETHYLBIPHENYL, also known as ortho-xylene, is a chemical compound composed of two methyl groups attached to a biphenyl molecule. It is a colorless liquid with a sweet odor and is commonly used as a solvent and in the production of other chemicals. It is flammable and may release toxic fumes when heated. 2,2'-DIMETHYLBIPHENYL is primarily used as a component in the production of polycarbonate and epoxy resins, as well as in the manufacture of dyes and pigments. It is also found in some household products, such as adhesives and sealants, and is used as a solvent in the manufacturing of rubber and plastics. Safety precautions should be taken when working with 2,2'-DIMETHYLBIPHENYL due to its flammability and potential for releasing harmful vapors.

Upstream product

• 2586-62-1 1-bromo-2-methylnaphtalene 
• 75-16-1 methylmagnesium bromide 
• 141807-44-5 (+/-)-2,2'-bis(trifluoromethanesulfonyloxy)-1,1-binaphthyl 
• 119906-95-5 4,5-dihydro-4,4-dimethyl-3H-dinaphtho<2,1-a:1',2'-e>stannepin 
• 91-57-6 2-Methylnaphthalene 
• 21450-90-8 (2-methyl-1-naphthyl)magnesium bromide 
• 54130-90-4 2,2'-di(bromomethyl)-1,1'-binaphthalene 
• 917-64-6 methyl magnesium iodide 
• 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 
• 594-27-4 tetramethylstannane 

Downstream Products

• 155825-57-3 4-phenyl-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 
• 515811-37-7 (S)-4-(4-methoxyphenyl)-4,5-dihydro-3H-dinaphtho[2,1-c;1',2'-e]phosphepine 
• 865095-85-8 rac-2,2'-bis[2,2-bis(4-methoxyphenyl)ethenyl]binaphthyl 
• 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 

Relevant articles and documents

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.

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