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

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

Uses

Used in Organic Synthesis:
2,2'-DIMETHYLBIPHENYL is used as a high temperature heat transfer fluid for its ability to withstand high temperatures without decomposing, which is crucial in various organic synthesis processes.
Used in Plastic Manufacturing:
In the plastic industry, 2,2'-DIMETHYLBIPHENYL serves as a heat transfer medium, ensuring efficient and uniform heating during the manufacturing process, which is essential for the production of high-quality plastics.
Used in Dye Production:
2,2'-DIMETHYLBIPHENYL is used as a raw material in the production of dyes, contributing to the creation of a wide range of colorants for various applications.
Used in Pharmaceutical Industry:
As a raw material, 2,2'-DIMETHYLBIPHENYL is utilized in the synthesis of pharmaceutical compounds, playing a role in the development of new drugs.
Used as a Polymer Stabilizer:
2,2'-DIMETHYLBIPHENYL is used to enhance the stability of certain polymers, acting as a stabilizer to prevent degradation and extend the polymer's lifespan.

Upstream product

• 2586-62-1 1-bromo-2-methylnaphtalene 
• 91-57-6 2-Methylnaphthalene 
• 21450-90-8 (2-methyl-1-naphthyl)magnesium bromide 
• 1528-01-4 methyltributyltin 
• 86688-06-4 (R_a)-2,2'-diiodo-1,1'-binaphthyl 
• 103989-84-0 2-methyl-1-naphthylboronic acid 
• 14221-01-3 tetrakis(triphenylphosphine) palladium⁽⁰⁾ 
• 54130-90-4 2,2'-di(bromomethyl)-1,1'-binaphthalene 
• 753-73-1 dimethyltin dichloride 
• 7439-95-4 magnesium 
• 70595-34-5 1,1'-bis(trimethylstannyl)ferrocene 
• 76905-80-1 (S)-2,2'-diiodo-1,1'-binaphthyl 
• 36374-82-0 1-iodo-2-methylnaphthalene 
• 1072849-07-0 C₁₄H₁₈OSi 

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 
• 515811-37-7 (S)-4-(4-methoxyphenyl)-4,5-dihydro-3H-dinaphtho[2,1-c;1',2'-e]phosphepine 

Relevant articles and documents

Asymmetric Synthesis Catalyzed by Chiral Ferrocenylphosphine-Transition-Metal Complexes. 6. Practical Asymmetric Synthesis of 1,1'-Binaphthyls via Asymmetric Cross-Coupling with a Chiral monophosphine/Nickel Catalyst.

Cross-coupling of (2-methyl-1-naphthyl)magnesium bromide (1a) with 2-methyl-1-naphthyl bromide (2a) at -15 or 0 deg C in the presence of nickel catalyst prepared in situ from nickel bromide and (S)-1-ethyl methyl ether (3a) gave high yield of (R)-(-)-2,2'-dimethyl-1,1'-binaphthyl (4a) in up to 95percent ee.Ferrocenylphosphine 3a was also effective for the reaction of 1a with 1-naphthyl bromide (2b) and that of (2-ethyl-1-naphthyl)magnesium bromide (1c) with 2b to give corresponding cross-coupling products in 83 and 77percent ee, respectively.

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

The X-ray Structures of (R)-2,2′-Dimethyl-1,1′-binaphthyl and (±)-2-Bromomethyl-2′-dibromomethyl-1,1′-binaphthyl

Molecular structures of (R)-2,2′-dimethyl-1,1′-binaphthyl [monoclinic, a = 11.24420 (11), b = 10.56190 (9), c = 13.27180 (13) ?, β = 90.7041 (9)°, space group P21] and (±)-2-bromomethyl-2′-dibromomethyl-1,1′-binaphthyl [triclinic, a = 9.4637 (14), b = 9.9721 (18), c = 9.9922 (19) ?, α = 100.093 (5), β = 97.141 (5), γ = 92.585 (4)°, space group P-1] are reported and compared with those of other simple 2,2′-disubstituted-1,1′-binaphthyls. Graphic Abstract: Inter-ring bond length and torsion angles are compared with other simple 2,2′-disubstututed-1,1′-binaphthyls.[Figure not available: see fulltext.]

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 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.

Reductive opening of 2,7-dihydrodinaphthoxepine and thiepine: Easy regioselective preparation of 2,2′-difunctionalised binaphthyls

The lithiation of 2,7-dihydrodinaphthoheteroepines (5) with 2.2 equiv of lithium naphthalenide in THF at -78°C gives dianionic intermediates 8, which by reaction with different electrophiles [H2O, D2O, tBuCHO, Me2CO, Et2CO, (CH2) 4CO, (CH2)5CO] at the same temperature, followed by hydrolysis, leads to unsymmetrically 2,2′-disubstituted binaphthyls 6. When the lithiation is performed with an excess of lithium in the presence of a catalytic amount of 4,4′-di-tert-butylbiphenyl (DTBB, 10 mol %), a double reductive cleavage takes place to give dianionic intermediate 9, which by reaction with different electrophiles [H2O, Me 2CO, Et2CO, (CH2)4CO, (CH 2)5CO], followed by hydrolysis with water, yields symmetrically 2,2′-disubstituted binaphthyls 7. In the case of starting from (R)-5a, the reductive opening by treatment with 2.2 equiv of lithium naphthalenide followed by reaction with H2O or (CH2) 5CO as electrophiles and final hydrolysis, leads to enantiomerically pure compounds (R)-6aa and (R)-6af, respectively.

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.

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

Design of Phosphinic Acid Catalysts with the Closest Stereogenicity at the α-Position: Synthesis and Application of α-Stereogenic Perfluoroalkyl Phosphinic Acid Catalysts

Chiral C2-symmetric phosphinic acids were designed based on sterically demanding and helical chiral perfluoroalkyl groups at the closest α-position advancing asymmetric reaction environment and catalytic activity. The perfluoroalkyl catalysts,