5006-39-3

Usage

Uses

Used in Chemical Synthesis:
1,1'-Biphenyl, 2,3,3',4'-tetramethylis used as a building block in the synthesis of various organic compounds due to its stability and reactivity. It serves as a key intermediate in the production of a wide range of chemical products.
Used in Polymer Production:
In the polymer industry, 1,1'-Biphenyl, 2,3,3',4'-tetramethylis used as a component in the synthesis of certain types of polymers. Its stability and chemical properties contribute to the development of polymers with specific characteristics, such as improved durability or resistance to environmental factors.
Used in Dye Manufacturing:
1,1'-Biphenyl, 2,3,3',4'-tetramethylis utilized in the production of dyes, where its chemical structure allows for the creation of dyes with unique color properties and stability. This makes it valuable in various applications, including textiles, printing, and other industries that require colorants.
Used in Pharmaceutical Development:
In the pharmaceutical sector, 1,1'-Biphenyl, 2,3,3',4'-tetramethylis employed in the development of new drugs. Its chemical properties make it a promising candidate for the synthesis of pharmaceutical compounds with potential therapeutic applications.
However, it is important to note that despite its widespread use, 1,1'-Biphenyl, 2,3,3',4'-tetramethylhas been subject to restrictions and regulations due to potential environmental and health concerns. This highlights the need for responsible handling and disposal of 1,1'-Biphenyl, 2,3,3',4'-tetramethyl- to minimize any adverse effects.

Upstream product

• 95-47-6 o-xylene 
• 615-60-1 4-chloro-1,2-dimethylbenzene 
• 608-23-1 3-chloro-o-xylene 
• 583-71-1 4-bromo-o-xylene 
• 31599-60-7 1-iodo-2,3-dimethylbenzene 
• 31599-61-8 3,4-dimethyliodobenzene 

Relevant academic research and scientific papers

Discovery and mechanistic investigation of Pt-catalyzed oxidative homocoupling of benzene with PhI(OAc)2

We present a Pt-catalyzed direct coupling of benzene to biphenyl. This catalytic reaction employs a cyclometalated platinum(ii) complex [PtMe(bhq)(SMe2)] (bhq = benzo[h]quinolate) with PhI(OAc)2 as an oxidant and does not require an acid, a co-catalyst or a solvent. The reaction kinetics and characterization of potential catalytic species are reported. The reaction is first-order in Pt and second-order in benzene, which implicates the second C-H activation step as rate-determining. A Pt(ii)/Pt(iv) catalytic cycle is suggested. The reaction commences by oxidation of the Pt(ii) complex to give the platinum(iv) species [Pt(bhq)(SMe2)(OAc)2](OAc) followed by C-H activation of benzene to afford the intermediate [PtPh(bhq)(SMe2)(OAc)](OAc) concurrently with the release of HOAc. A second benzene molecule reacts similarly to give the diphenyl intermediate [PtPh2(bhq)(SMe2)](OAc). C-C bond forming reductive elimination ensues to regenerate Pt(ii) and complete the catalytic cycle. The proposed mechanism has been examined by DFT computations, which provide support to experimental findings.

Single-site metal-organic framework catalysts for the oxidative coupling of arenes: Via C-H/C-H activation

C-H activation reactions are generally associated with relatively low turnover numbers (TONs) and high catalyst concentrations due to a combination of low catalyst stability and activity, highlighting the need for recyclable heterogeneous catalysts with stable single-atom active sites. In this work, several palladium loaded metal-organic frameworks (MOFs) were tested as single-site catalysts for the oxidative coupling of arenes (e.g. o-xylene) via C-H/C-H activation. Isolation of the palladium active sites on the MOF supports reduced Pd(0) aggregate formation and thus catalyst deactivation, resulting in higher turnover numbers (TONs) compared to the homogeneous benchmark reaction. Notably, a threefold higher TON could be achieved for palladium loaded MOF-808 due to increased catalyst stability and the heterogeneous catalyst could efficiently be reused, resulting in a cumulative TON of 1218 after three runs. Additionally, the palladium single-atom active sites on MOF-808 were successfully identified by Fourier transform infrared (FTIR) and extended X-ray absorption fine structure (EXAFS) spectroscopy.

Palladium-Catalyzed Cross-Dehydrogenative Coupling of o-Xylene: Evidence of a New Rate-Limiting Step in the Search for Industrially Relevant Conditions

An efficient cross-dehydrogenative coupling of o-xylene under neat conditions, which brings important industrial benefits towards the synthesis of a monomer used in polyimide resins, is reported. The catalyst based on the combination of Pd/N ligand/carboxylate=1:1:2 does not require a Cu cocatalyst and proceeds at 11 bar of O2 pressure. Evaluation of the deuterium kinetic isotope effect (KIE) provides evidence for three different rate-determining steps, which depend on the reaction conditions (medium, temperature). Under the reported neat conditions, the dissociation of a carboxylate-bridged dimer to generate a more reactive monometallic Pd species is proposed to be the rate-limiting step.

A four methyl biphenyl isomer preparation method

The invention discloses a preparation method of tetramethylbiphenyl isomers. By adopting an alkyl-substituted tetrahydrofuran with a boiling point of above 80 DEG C, low toxicity and non water solubility as a solvent system, halogenated o-xylene as a raw material, magnetism as a reducing agent, and a complex formed by salts of transition metals such as nickel, copper, iron, magnesium or cobalt, or additives such as organophosphorus and organic amine as a catalyst, 3,3'4,4'-tetramethylbiphenyl, 2,3'3,4'-tetramethylbiphenyl and 2,2'3,3'-tetramethylbiphenyl isomers are prepared by adopting a coupled reaction. According to the preparation method, the cyclic utilization rate of the solvent reaches above 90 percent, and the yield of compounds of the tetramethylbiphenyl isomers reaches 85-95 percent.

A method for preparing four methyl biphenyl

The invention provides a preparation method of tetramethyl biphenyl, which comprises the following steps: mixing halogenated o-xylene, magnesium metal, iodine, ether and transition metal catalyst, and reacting to obtain the tetramethyl biphenyl, wherein the mol ratio of ether to magnesium metal is (0.5-3):1. Compared with the prior art of synthesizing tetramethyl biphenyl from halogenated o-xylene, the invention has the following advantages: by using the raw material halogenated o-xylene as the solvent, the preparation of the format reagent and the coupling reaction are carried out in the initial raw material, so that the addition of abundant anhydrous solvent as the reaction medium is not needed, thereby lowering the reaction cost and simplifying the production technique; the magnesium metal is directly added into the halogenated o-xylene to obtain the format reagent, so the process is simple and the conditions are mild and controllable; and the raw material, the concentration of which in the reaction system is high, is used as the solvent and participates in the oxidation-reduction process in the coupling reaction, no oxidizer is needed, so the reaction conditions are mild and controllable.

A method for preparing four methyl biphenyl

The invention provides a preparation method of tetramethyl biphenyl, which comprises the following steps: mixing o-xylene, oxidizer, additive and metal catalyst, and reacting to obtain the tetramethyl biphenyl, wherein the additive is organic acid and/or organic acid anhydride, and the oxidizer is inorganic oxidizer and/or organic oxidizer containing metal cation. Compared with the prior art of synthesizing tetramethyl biphenyl from halogenated o-xylene, the invention uses the o-xylene for direct coupling to obtain the tetramethyl biphenyl. The raw material o-xylene is cheap and accessible, and the preparation of the halogenated o-xylene is not needed, so the invention lowers the production cost, is simple to operate and has the advantages of mild reaction conditions and low facility request; and under the action of the catalyst, the o-xylene is directly coupled to prepare the tetramethyl biphenyl, and all the carbon atom frameworks of the o-xylene enter the product, so the invention also has the advantage of high economical efficiency of atoms.

A 2, 3, 3 ', the 4 [...] -tetramethyl-biphenyl preparation method

The invention provides a preparation method of 2,3,3'4'-tetramethyl biphenyl. The preparation method comprises the following steps of: mixing a compound in the structure shown in formula (I) and a compound in the structure shown in formula (II), and carrying out cross coupling reaction on the mixture with the existence of a catalyst to obtain 2,3,3'4'-tetramethyl biphenyl; or, mixing a compound in the structure shown in formula (III) and a compound in the structure shown in formula (IV), and carrying out cross coupling reaction on the mixture with the existence of a catalyst to obtain 2,3,3'4'-tetramethyl biphenyl, wherein X1 is fluorine, chlorine, bromine or iodine; X2 is fluorine, chlorine, bromine or iodine; X3 is fluorine, chlorine, bromine or iodine; X4 is fluorine, chlorine, bromine or iodine; the catalyst is iron, nickel, copper, cobalt, a compound of iron, a compound of nickel, a compound of copper, a compound of cobalt, or a catalysis system formed from a ligand with a compound of iron, nickel, copper and cobalt, the compound of iron, the compound of nickel, the compound of copper, or the compound of cobalt.

PROCESS FOR THE PRODUCTION OF BIARYL COMPOUNDS

Process for producing biaryl compounds by aerobic cross dehydrogenative coupling (CDC) of two arene groups comprising at least one aryl carbon-hydrogen bond, in the presence of a catalyst system comprising a palladium salt comprising at least one non-cyclopalladatable carboxylate anion and one or more non-beta-eliminatable, non-cyclopalladatable ligands comprising at least one N-donor atom, the one or more ligands having a 0.5/1 - 1.5/1 molar ratio of N-donor atoms relative to the Pd atoms.

Aerobic oxidative coupling of o-xylene: Discovery of 2-fluoropyridine as a ligand to support selective Pd-catalyzed C-H functionalization

An improved method for the direct oxidative coupling of o-xylene could provide streamlined access to an important monomer used in polyimide resins. The use of 2-fluoropyridine as a ligand has been found to enable unprecedented levels of chemo- and regioselectivity in this palladium-catalyzed aerobic oxidative coupling reaction. Preliminary insights have been obtained into the origin of the effectiveness of 2-fluoropyridine as a ligand. Copyright

The Reductive Coupling of Organic Halide Using Hydrazine and a Palladium Amalgam Catalyst. I. The Preparation of Biaryls

Iodoarenes could be converted to the corresponding biaryls in high yields by use of a catalytic amount of a palladium amalgam in place of a palladium-calcium carbonate catalyst in Busch's reaction.The 2,3'-isomer content in the bitolyls obtained by the homo-coupling of o-iodotoluene was 15percent when palladium was used, while it was 1percent when a palladium amalgam was used, and the latter was re-usable.The present method is further applicable to some iodoalkanes.