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Usage

Uses

Used in Liquid Crystal Material Production:
BIPHENYL-3,3'-DICARBOXYLIC ACID DIMETHYL ESTER is used as a key intermediate for the production of liquid crystal materials, which are essential components in electronic display screens. Its unique molecular structure contributes to the formation of liquid crystals with specific properties, enhancing the performance of electronic devices.
Used in Polyester Resin Manufacturing:
In the polyester resin industry, BIPHENYL-3,3'-DICARBOXYLIC ACID DIMETHYL ESTER is utilized as a chemical intermediate to produce high-quality resins. These resins are known for their excellent mechanical, thermal, and chemical resistance properties, making them suitable for various applications, such as coatings, adhesives, and composite materials.
Used in Electronic Display Screen Manufacturing:
BIPHENYL-3,3'-DICARBOXYLIC ACID DIMETHYL ESTER is used as a critical component in the manufacturing of electronic display screens. Its role in liquid crystal material production directly impacts the quality and performance of these screens, contributing to the advancement of electronic devices and displays.
Used in Film and Fiber Production:
BIPHENYL-3,3'-DICARBOXYLIC ACID DIMETHYL ESTER is also used in the production of films and fibers, where its properties contribute to the development of materials with specific characteristics. These films and fibers find applications in various industries, such as packaging, textiles, and automotive, due to their unique properties.
Used as a Chemical Intermediate in Pharmaceutical Synthesis:
BIPHENYL-3,3'-DICARBOXYLIC ACID DIMETHYL ESTER plays a significant role as a chemical intermediate in the synthesis of pharmaceuticals. Its versatile properties allow for the development of new drugs and medications, contributing to advancements in healthcare and medicine.
Used in Dye and Pesticide Synthesis:
Furthermore, BIPHENYL-3,3'-DICARBOXYLIC ACID DIMETHYL ESTER is utilized as a chemical intermediate in the synthesis of dyes and pesticides. Its involvement in these industries enables the creation of new and improved products, enhancing their performance and effectiveness.

Upstream product

• 67-56-1 methanol 
• 612-87-3 biphenyl-3,3'-dicarboxylic acid 
• 618-91-7 methyl 3-iodo-benzoate 
• 618-89-3 methyl 3-bromobenzoate 
• 148651-38-1 3-methoxycarbonylphenylzinc iodide 
• 2905-65-9 methyl 3-chlorobenzoate 
• 19438-10-9 methyl 3-hydroxybenzoate 
• 99769-19-4 [3-(methoxycarbonyl)phenyl]boronic acid 
• 108-86-1 bromobenzene 
• 13531-48-1 methyl 3-cyanobenzoate 
• 168085-14-1 C₉H₇O₄^(1-)*Na⁽¹⁺⁾ 
• 107658-28-6 methyl 3-(trifluoromethylsulfonyloxy)benzoate 
• 480425-35-2 methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate 
• 1722-10-7 3-chloro-6-methoxypyridazine 

Downstream Products

• 53074-63-8 3,3'-Bis-di(biphenyl-4-yl)hydroxymethyl-biphenyl 
• 146364-76-3 3,3'-bis(diphenylhydroxymethyl)biphenyl 
• 53074-65-0 3,3'-Bis-di-(biphenyl-4-yl)-chlormethyl-biphenyl 

Relevant academic research and scientific papers

Palladium-catalyzed benzoin-mediated redox process leading to biaryls from aryl halides

An expedient synthetic procedure of biaryl derivatives was developed using a palladium-catalyzed, benzoin-mediated redox process from aryl halides. Various biaryls were synthesized in good yields in short time.

The Oxidative Coupling of Methyl Benzoate

The reaction of methyl benzoate (MBA) with pressurized (50 atm) artificial air (50 mol% O2-N2 mixture) at 150-200°C over a soluble palladium catalyst [PdLL2′] (L=phen, bipy, dppe; L′=OAc, TFA) afforded isomeric dimethyl bibenzoic acid esters (DMBBA). Different factors affect the reactivity and regioselectivity of the process. The reactivity is enhanced by trifluoromethanesulfonic acid, arguably by activating the C-H bond of the aromatic ring by its protonation. The increase of temperature not only increases the reaction rate (EA=5.5 kcal/mol) but also favors a formation of an ortho-coupled product. Ligands with strong trans influence (L=phen, bipy, or dppe) direct the oxidative coupling away from 2,X′-isomers (X=2, 3, or 4). Overall, electronic properties of a palladium catalyst are more important than steric restriction of the same catalyst for altering the activity and regioselectivity for MBA coupling.

The coupling of aryl halides in the ionic liquid [bmim]PF6

Several aryl halides have been coupled using the zero valent nickel catalyst [(PPh3)(n)Ni(0)], to give the biaryl in moderate to good yield, employing the ionic liquid [bmim]PF6. The ionic liquid and catalyst were recycled after extraction of the biaryl. (C) 2000 Elsevier Science Ltd.

New Role of CO2 as a Selective Agent in Palladium-Catalyzed Reductive Ullmann Coupling with Zinc in Water

Carbon dioxide was found to promote the palladium-catalyzed zinc-mediated reductive Ullmann coupling of aryl halides. In the presence of carbon dioxide, Pd/C, and zinc, various aromatic halides including less reactive aromatic chlorides were coupled to give the corresponding homocoupling products in good yields.

Pd-Catalyzed desulfitative arylation of olefins by: N -methoxysulfonamide

A novel Pd-catalyzed protocol for the desulfitative Heck-type reaction of N-methoxy aryl sulfonamides with alkenes was reported. The cross-coupling reaction was performed successfully with a variety of olefins to obtain aryl alkenes. Different substituents on the aromatic ring of N-methoxysulfonamides were also found to be compatible with the reaction conditions. Expectedly, the reaction proceeds through CuCl2-promoted generation of the nitrogen radical and subsequent desulfonylation under thermal conditions to afford the aryl radical for the Pd-catalyzed coupling reaction. N-Methoxysulfonamide was further exploited for the synthesis of symmetrical biaryls in the presence of CuCl2. This journal is

Visible Light Induced Aerobic Coupling of Arylboronic Acids Promoted by Hydrazone

A visible-light-induced oxidative coupling of arylboronic acids has been developed for the synthesis of biaryls. The reaction that employs polydentate hydrazones as the bifunctional catalyst works smoothly under room temperature. It is compatible with a w

Reductive Coupling of Aryl Halides via C—H Activation of Indene

This paper describes the first case of a reductive coupling reaction with indene, a non-heteroatom olefin used as a reducing agent. The scope of the substrate is wide. The homo-coupling, cross-coupling, and synthesis of 12 and 14-membered rings were realized. The control experiment, indene-product curve and density functional theory calculations showed that the η3-palladium indene intermediate was formed by C—H activation in the presence of cesium carbonate. We speculate that the final product was obtained through a Pd (IV) intermediate or aryl ligand exchange. In addition, we excluded the formation of palladium anion (Pd(0)?) intermediates.

Pd-catalyzed oxidative homocoupling of arylboronic acids in WEPA: A sustainable access to symmetrical biaryls under added base and ligand-free ambient conditions

Symmetrical and unsymmetrical biaryls comprises a diverse class of biologically eloquent organic compounds. We herein report, a quick and eco-friendly protocol for the synthesis of biaryls by an oxidative (aerobic) homocoupling of arylboronic acids (ABAs) using Pd(OAc)2 in water extract of pomogranate ash (WEPA) as an efficient agro-waste(bio)-derived aqueous (basic) media. The reactions were executed at ambient aerobic conditions in the absence of external base and ligand to result symmetrical biaryls in excellent yields. The use of renewable media with an effective exploitation of waste, short reaction times, excellent yields of products, easy separation of the products, unnecessating the external base, oxidant, ligand or volatile organic solvents and ambient reaction conditions are the vital insights of the present protocol.

Cobalt-catalyzed C(sp2)?CN bond activation: Cross-electrophile coupling for biaryl formation and mechanistic insight

Herein, we report a cross-electrophile coupling of benzonitrile derivatives and aryl halides with a simple cobalt-based catalytic system under mild conditions to form biaryl compounds. Even though the cobalt catalyst is able to activate the C(sp2)?CN bond alone, the use of the AlMe3 Lewis acid enhances the reactivity of benzonitriles and improves the cross-selectivity with barely any influence on the functional group compatibility. X-ray structure determination of an original low-valent cobalt species combined with catalytic and stoichiometric reactions reveals a catalytically active cobalt(I) species toward the aryl halide partner. On the other hand, experimental insights, including cyclic voltammetry experiments, suggest the involvement of a cobalt complex of a lower oxidation state to activate the benzonitrile derivative. Finally, density functional theory calculations support the proposed mechanistic cycle involving two low-valent cobalt species of different oxidation states to perform the reaction.

A Bio-Inspired Magnetically Recoverable Palladium Nanocatalyst for the Ullmann Coupling reaction of Aryl halides and Arylboronic acids In Aqueous Media

Palladium nanoparticles supported on polydopamine-coated iron oxide nanoparticles (Pd/Fe3O4@PDA) were found to catalyze the Ullmann homocoupling of a wide variety of aryl halides, arylboronic acids and aryldiazonium salts in aqueous media in the presence of randomly methylated β-cyclodextrin (RM-β-CD). The synthesized nanoparticles were characterized by techniques such as TEM, SEM, EDX, XPS, ICP-AES and XRD. The synthesized catalyst can be easily recovered magnetically and reused up to five cycles without any significant loss of activity. This is the first report demonstrating the use of magnetically recoverable catalyst for Ullmann homocoupling reactions of aryl halides, arylboronic acids and aryldiazonium salts in water.