605-39-0

Basic information

• Product Name: 2,2'-DIMETHYLBIPHENYL
• Synonyms: 2,2'-DIMETHYLBIPHENYL;2,2'-BITOLYL;O,O'-BITOLUENE;O,O'-BITOLYL;(R)-2,2'-DIMETHYL-1,1'-BINAPHTHYL;(S)-2,2'-DIMETHYL-1,1'-BINAPHTHYL;1,1'-Biphenyl, 2,2'-dimethyl-;1-Methyl-2-(2'-methylphenyl)benzene
• CAS NO: 605-39-0
• Molecular Formula: C₁₄H₁₄
• Molecular Weight: 182.26
• Product Categories: Biphenyls (for High-Performance Polymer Research);Functional Materials;Reagent for High-Performance Polymer Research;OLED
• Mol File: 605-39-0.mol
• Article Data: 369

Chemical Properties

• Melting Point: 18°C
• Boiling Point: 259 °C
• Flash Point: >230 °F
• Appearance: /
• Density: 0.989 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0253mmHg at 25°C
• Refractive Index: n20/D 1.5745(lit.)
• CAS DataBase Reference: 2,2'-DIMETHYLBIPHENYL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-DIMETHYLBIPHENYL(605-39-0)
• EPA Substance Registry System: 2,2'-DIMETHYLBIPHENYL(605-39-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 605-39-0(Hazardous Substances Data)

Usage

General Description

2,2'-Dimethylbiphenyl is a chemical compound consisting of a biphenyl molecule with two methyl groups attached to the 2nd carbon atoms on each phenyl ring. It is a colorless liquid at room temperature with a melting point of 84-86 degrees Celsius and a boiling point of 271-273 degrees Celsius. 2,2'-Dimethylbiphenyl is used as a high-temperature heat transfer medium in various applications such as heat transfer fluids, lubricants, and as a precursor for the synthesis of other organic compounds. It is also used in the electronics industry as a component of heat transfer fluids in immersion cooling systems for electronic devices. However, 2,2'-dimethylbiphenyl may be harmful if inhaled, swallowed, or absorbed through the skin, and it is considered a possible human carcinogen. Therefore, proper safety measures should be taken when handling and using this chemical.

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

• 615-37-2 ortho-methylphenyl iodide 
• 38274-14-5 2,2'-bis-(bromomethyl)-1,1'-biphenyl 
• 5060-10-6 2-Methyl-1-o-tolyl-cyclohexanol 
• 84-67-3 2,2'-dimethylbenzidine 
• 6699-93-0 (2-methylphenyl)lithium 
• 932-31-0 ortho-tolylmagnesium bromide 
• 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

• 776-35-2 9,10-dihydrophenanthrene 
• 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 
• 85-01-8 phenanthrene 
• 1556-99-6 4-methylfluorene 
• 167547-47-9 2,2'-bis-[2,2-bis-(4-methoxy-phenyl)-vinyl]-biphenyl 
• 1392203-19-8 3,3′-diiodo-6,6′-dimethylbiphenyl 
• 1429868-89-2 C₅₆H₆₂O₄ 
• 1429868-99-4 C₅₆H₆₆O₆ 
• 1429868-87-0 C₇₂H₉₄O₄ 
• 1429868-93-8 C₇₂H₉₄O₄ 
• 1429869-01-1 C₇₂H₉₈O₆ 
• 1429868-98-3 C₇₂H₉₈O₆ 

Relevant articles and documents

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.

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.

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.

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.

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.

Mechanistic insights into the C-S bond breaking in dibenzothiophene sulfones

The reactivity of Grignard reagents in the presence of nickel catalysts is known to be highly efficient in the deoxydesulfurization of dibenzothiophene sulfone (DBTO2), 4-methyldibenzothiophene (4-MeDBTO2), and 4,6-dimethyldibenzothiophene (4,6-Me2DBTO2), to yield sulfur-free biphenyls via cross-coupling reactions. However, the mechanistic details involved in the process remained unknown. In this report the reactivity of [(dippe)Pt(μ-H)]2 with DBTO2 turned out to be catalytically less efficient compared with [(dippe)Ni(μ-H)]2, but the first allowed the isolation and full characterization of several reaction intermediates, such as [(dippe)Pt(κ2-C,S-DBTO2)]. It was demonstrated that this is a key intermediate in all the deoxydesulfurization reactions of the above-mentioned aromatic sulfones (DBTsO2).

Silk?Fibroin-Supported Palladium Catalyst for Suzuki-Miyaura and Ullmann Coupling Reactions of Aryl Chlorides

Recently, we have reported the preparation of a silk fibroin-supported Palladium catalyst (Pd/SF) and its use in the Suzuki-Miyaura cross-coupling of aryl iodides. Since its synthetic applicability and structural features are still far from being fully ex

Identification of a Nitrenoid Reductive Elimination Pathway in Nickel-Catalyzed C-N Cross-Coupling

Whereas the (bisphosphine)Ni-catalyzed C-N cross-coupling of (hetero)aryl (pseudo)halides with NH nucleophiles represents a useful method for the synthesis of (hetero)anilines, our mechanistic understanding of such cross-couplings is incomplete, especially regarding key C-N reductive elimination steps that are often invoked as turnover-limiting. In this combined experimental and computational study, we provide evidence of a bifurcated C-N reductive elimination pathway for cross-couplings of tBuNH2 and (aryl′)SO2NH2 employing (L1)Ni(aryl)Cl as the precatalyst (L1 = PhPAd-DalPhos). In contrast with direct C-N reductive elimination that proceeds from the nickel alkylamido complex (L1)Ni(aryl)(NHtBu), we provide evidence of a previously undocumented base-promoted pathway involving deprotonation of the nickel sulfonamido complex (L1)Ni(aryl)(NHSO2(aryl′)) to give the anionic nickel nitrenoid species [(L1)Ni(aryl)(NSO2(aryl′))]-, from which C-N reductive elimination occurs preferentially.