19634-89-0

Basic information

• Product Name: 2,2'-DIMETHYLBIPHENYL
• Synonyms: (S)-2,2'-DIMETHYL-1,1'-BINAPHTHYL;(R)-2,2'-DIMETHYL-1,1'-BINAPHTHYL;O,O'-BITOLUENE;O,O'-BITOLYL;2,2'-DIMETHYLBIPHENYL;2,2'-BITOLYL;R-2,2'-DiMethyl-1,1'-binaphthalene;(R)-2,2'-Dimethyl-1,1'-binaphthyl
• CAS NO: 19634-89-0
• Molecular Formula: C₂₂H₁₈
• Molecular Weight: 182.26
• Mol File: 19634-89-0.mol
• Article Data: 88

Chemical Properties

• Melting Point: 84 °C
• Boiling Point: 401.8±30.0 °C(Predicted)
• 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(19634-89-0)
• EPA Substance Registry System: 2,2'-DIMETHYLBIPHENYL(19634-89-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 19634-89-0(Hazardous Substances Data)

Usage

General Description

2,2'-DIMETHYLBIPHENYL, also known as 2,2'-Biphenyl, 2,2'-Biphenyl, 2',2''-Dimethyl-, is an aromatic hydrocarbon compound with the chemical formula C14H14. It is a white, crystalline solid with a melting point of 92-94°C. This chemical is commonly used as a high temperature heat transfer fluid in various industrial processes such as organic synthesis and plastic manufacturing. It is also utilized as a raw material in the production of dyes, pharmaceuticals, and as a stabilizer in some polymers. Due to its potential effects on human health and the environment, it is important to handle and dispose of 2,2'-DIMETHYLBIPHENYL in accordance with safety regulations and guidelines.

Upstream product

• 2586-62-1 1-bromo-2-methylnaphtalene 
• 21450-90-8 (2-methyl-1-naphthyl)magnesium bromide 
• 103989-84-0 2-methyl-1-naphthylboronic acid 
• 5859-45-0 1-chloro-2-methylnaphthalene 
• 36374-82-0 1-iodo-2-methylnaphthalene 
• 312303-50-7 2-(2-methyl-naphthalen-1-yl)-[1,3,2]dioxaborolane 
• 75-16-1 methylmagnesium bromide 
• 128544-05-8 (R)-(-)-1,1'-bi-2-naphthol triflate 
• 917-64-6 methyl magnesium iodide 
• 86688-06-4 (R_a)-2,2'-diiodo-1,1'-binaphthyl 
• 75-24-1 trimethylaluminum 
• 18815-73-1 methylzinc iodide 
• 74-88-4 methyl iodide 
• 18741-85-0 (R)-1,1'-binaphthyl-2,2'-diamine 

Relevant articles and documents

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

4,5-Dihydro-4,4-dimethyl-3H-dinaphthostannepin as a Precursor of 2,2'-Bis(lithiomethyl)-1,1'-binaphthyl

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An enantioselective artificial Suzukiase based on the biotin-streptavidin technology

Introduction of a biotinylated monophosphine palladium complex within streptavidin affords an enantioselective artificial Suzukiase. Site-directed mutagenesis allowed the optimization of the activity and the enantioselectivity of this artificial metalloenzyme. A variety of atropisomeric biaryls were produced in good yields and up to 90% ee. The hybrid catalyst described herein shows comparable TOF to the previous aqueous-asymmetric Suzuki catalysts, and excellent stability under the reaction conditions to realize higher TON through longer reaction time.

Synthesis of binaphthyl derivatives through radical cation formation

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Asymmetric Negishi reaction for sterically hindered couplings: synthesis of chiral binaphthalenes

A new synthetic approach affording, for the first time chiral binaphthalene derivatives via an asymmetric Negishi reaction, in good yields (55-95%) and good enantioselectivities (49-85% ee), is reported.

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

Large Scale Synthesis of Chiral (3 Z,5 Z)-2,7-Dihydro-1H-azepine-Derived Hamari Ligand for General Asymmetric Synthesis of Tailor-Made Amino Acids

An advanced process for large scale (500 g) preparation of a (3Z,5Z)-2,7-dihydro-1H-azepine-derived chiral tridentate ligand (Hamari ligand), widely used for asymmetric synthesis of tailor-made α-amino acids via the corresponding glycine Schiff base Ni(II