605-39-0

Usage

Uses

Used in Heat Transfer Fluids:
2,2'-Dimethylbiphenyl is used as a high-temperature heat transfer medium for its thermal stability and low vapor pressure, making it suitable for applications in heat transfer fluids, lubricants, and as a precursor in the synthesis of other organic compounds.
Used in Electronics Industry:
In the electronics industry, 2,2'-Dimethylbiphenyl is utilized as a component of heat transfer fluids in immersion cooling systems for electronic devices, providing efficient cooling solutions for high-performance systems.
Used in Chemical Synthesis:
2,2'-Dimethylbiphenyl serves as a precursor in the synthesis of various organic compounds, contributing to the development of new materials and chemical products.
Safety Considerations:

InChI:InChI=1/C14H14/c1-11-7-3-5-9-13(11)14-10-6-4-8-12(14)2/h3-10H,1-2H3

Upstream product

• 932-31-0 ortho-tolylmagnesium bromide 
• 615-37-2 ortho-methylphenyl iodide 
• 38274-14-5 2,2'-bis-(bromomethyl)-1,1'-biphenyl 
• 22077-56-1 di-2-tolyl selenide 
• 95-53-4 o-toluidine 
• 78-88-6 2,3-Dichloroprop-1-ene 
• 917-64-6 methyl magnesium iodide 
• 132-65-0 dibenzothiophene 
• 74-88-4 methyl iodide 
• 201230-82-2 carbon monoxide 
• 104089-17-0 ethyl 4-(iodozincio)butanoate 
• 95-49-8 2-methylchlorobenzene 
• 30930-49-5 bis(2-thiophenecarbonyl) peroxide 
• 108-88-3 toluene 

Downstream Products

• 85-01-8 phenanthrene 
• 1556-99-6 4-methylfluorene 
• 38274-14-5 2,2'-bis-(bromomethyl)-1,1'-biphenyl 
• 90732-71-1 2-bromomethyl-2'-methyl-biphenyl 
• 776-35-2 9,10-dihydrophenanthrene 
• 117713-05-0 Tricyclo[13.4.0.0^2,7]nonadeca-1⁽¹⁵⁾,2⁽⁷⁾,3,5,16,18-hexaene 
• 1015-80-1 6,7-dihydro-5H-dibenzo[a,c][7]annulene 
• 117713-21-0 2'-Methyl-2-vinyl-biphenyl 
• 90732-77-7 6,7-dihydro-6,6-dimethyl-5H-dibenzo-silepine 
• 117713-20-9 2-Isobutyl-2'-methyl-biphenyl 
• 117712-96-6 2,2'-di(s-butyl)biphenyl 
• 51744-98-0 [2.2]Metacyclophan 
• 117773-79-2 <2>(1,3)Benzeno<2>(2,2')biphenylophan 
• 597579-88-9 2,2'-bis[2,2-bis(4-dimethylaminophenyl)ethenyl]biphenyl 

Relevant academic research and scientific papers

Photochemistry of Singlet and Upper Triplet States of Dibenzocycloheptadienone

Dibenzocycloheptadienone (1) undergoes Norrish type I α-cleavage from both its first excited singlet state and an upper triplet state with quantum yields of 0.02 and 0.04, respectively.The major product in both cases in dihydrophenanthrene formed by loss of carbon monoxide from the initial biradical, followed by ring closure.The triplet state of ketone 1 has been characterized by laser flash photolysis.Photolysis of the triplet leads to irreversible bleaching and the generation of a short-lived (ca. 350 ns) transient at 325 nm, which is tentatively assigned to biradical 3.

Suzuki reactions catalyzed by palladium complexes bearing the bulky (2,6-dimesitylphenyl)dimethylphosphine

Good yields for coupling of aryl halides with arylboronic acids are achieved utilizing a (m-terphenyl)dialkylphosphine palladium complex. A new bulky and stable phosphine (2,6-dimesitylphenyl)dimethylphosphine, and representative palladium complexes have been prepared and structurally characterized; some of these complexes prove efficient for coupling of aryl chlorides with arylboronic acids.

Water Soluble Benzimidazole Containing Ionic Palladium(II) Complex for Rapid Microwave-Assisted Suzuki Reaction of Aryl Chlorides

In this paper a water soluble benzimidazole – Pd complex used for Suzuki reaction under conventional heating and microwave heating. To increase the activity of complex, ionic group change with bulky TBA+ and Bmim+ groups. To determine whether the reaction is homogeneous or heterogeneous, Hg(0) poisoning tests, hot filtration tests and CS2 poisoning tests were performed.

Catalytic desulfurization of dibenzothiophene using nickel supported on cross-linked polystyrene-PPh3 catalysts

Nickel catalysts supported on a cross-linked polystyrene-PPh3 resin were easily prepared in different oxidation states (0 and II) and used (0.1 mol% Ni) in conjunction with MeMgBr to achieve the desulfurization of dibenzothiophene (DBT), result

Synthesis and use of trans-dichlorido-tetrakis-(N-R-imidazole)nickel(II) complexes in Kumada-Tamao-Corriu cross-coupling reactions

Two dichlorido-tetrakis-(N-R-imidazole)nickel(II) complexes (R = 2,6-diisopropylphenyl (1); methyl (2)) have been synthesised. A single crystal X-ray diffraction study was carried out for 1, which revealed a centrosymmetric complex with the nickel centre placed in an octahedral coordination environment. Both complexes showed high activities (TOFs up to 60200 mol(ArBr) mol(Ni) -1 h-1) in Kumada-Tamao-Corriu cross-coupling of arylhalides with arylgrignards. No significant differences in activity were observed between the two complexes.

A New Assisted Reaction in the Photodecomposition Reaction of Dibenzoyl Peroxide

2,2'-, 2,3'-, and 3,3'-Dimethylbiphenyls were found in the photodecomposition reaction of dibenzoyl peroxide using toluene as solvent.We carried out the experiments to study the external magnetic field, oxygen scavenging, and excitation light intensity effects on their yields.It is concluded that they are produced through the dimerization of (benzoyloxy)methylcyclohexadienyl radicals.This is a new case of the assisted reaction by benzoyloxyl radical.The yields of dimethylbiphenyls were found to be affected remarkably by the small variation of the concentration of benzoyloxyl radical through the three experiments.

A Re-examination of the Sonochemical Coupling of Bromoaryls.

The sonochemical coupling of bromotoluenes leads to a mixture of isomeric bitolyls suggesting a radical mechanism, confirmed using radical scavengers which inhibit the reaction.

Synthesis of a C3-symmetric ferrocenylphosphine and its application to the Suzuki reaction of aryl chlorides

(pS,pS,pS)-Tris(2-methylferrocenyl)phosphine 1 was synthesised in 62% yield from (S)-2-ferrocenyl-4-(1-methylethyl)oxazoline. In combination with Pd2dba3 this novel C3-symmetric ligand generates a catalyst for the Suzuki reaction of aryl chloride substrates, these reactions proceed readily at 60°C in dioxane.

TEMPO-mediated homocoupling of aryl Grignard reagents: Mechanistic studies

The mechanism of the TEMPO mediated oxidative homo-coupling of aryl Grignard reagents is investigated in detail by experimental and computational studies. Experimental data reveal that the nitroxide-mediated homocoupling reaction of aryl Grignard reagents does not occur via free aryl radicals. Evidence for the presence of biaryl radical anions as intermediates in the coupling reaction is provided. It is also shown that PhMgPh under bromide free conditions in the presence of TEMPO does not undergo homocoupling. However, upon addition of MgBr2, C-C bond formation smoothly proceeds documenting the important role of the bromide anions in the oxidative homocoupling. DFT calculations show that an intramolecular electron transfer to a Mg-complexed TEMPO ligand with subsequent biaryl formation in a dimeric complex is viable and in agreement with experimental reaction conditions. This journal is

Synthesis of monodentate ferrocenylphosphines and their application to the palladium-catalyzed Suzuki reaction of aryl chlorides

Racemic and enantiopure (pS)-1-bromo-2-methylferrocene 6 were synthesized in 4 steps from 2-(4,4-dimethyloxazolinyl)ferrocene and (S)-2-(4-methylethyloxazolinyl)ferrocene, respectively (46 and 81% overall yield). Bromolithium exchange and addition of ClPR2 gave the corresponding racemic or enantiopure 2-methylferrocenyl phosphine ligands 2-MeFcPR2 11 (R = Ph), 12 (R = Cy), and 13 (R = tBu) in 28-93% yield. Use of PCl3 gave the C3-symmetric phosphine (2-MeFc)3P 5 from (pS)-6 (72% yield) but racemic 6 did not lead to the formation of triferrocenyl phosphines. Combination of 5 and Pd2(dba)3 gave an active catalyst for the Suzuki reaction of aryl chlorides, for example, 4-chlorotoluene and phenylboronic acid reacted at only 60 °C in dioxane (86% yield). Other examples are reported together with the use of 12 in this same protocol. From the X-ray crystal structure of 5 the cone angle was determined as 211°. With this, and the electronic character of 11, 12, and other phosphines (derived from vco of trans-[(R3P)2Rh(CO)Cl]), an analysis is made of the steric and electronic influences on ligand activity in the Suzuki reaction.