Production Method 1

92-86-4

792-74-5

Reaction Conditions

1.1 Reagents: Triethylamine Catalysts: Bis(benzonitrile)dichloropalladium (complex with (diphenylphosphino)methylated polystyrene) Solvents: Tetrahydrofuran

Reference

Preparation of aromatic dicarboxylic acid diesters

, Japan, , ,

Production Method 2

619-44-3

792-74-5

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: (SP-4-3)-Chloro[4-[[1,4-dioxo-4-[[3-(trimethoxysilyl)propyl]amino]butyl]amino]-2… (Fe3O4 MNP-supported) Solvents: Dimethylformamide ;  12 h, 110 °C

Reference

The role of magnetic nanoparticles (MNP) as reducing agents in an MNP-supported Pd-catalyst for the reductive homocoupling of aryl halides

Zheng, Jie; Lin, Shengyue; Jiang, Bi-Wang; Marder, Todd B.; Yang, Zhen, Canadian Journal of Chemistry, 2012, 90(1), 138-144

Production Method 3

161497-18-3

792-74-5

Reaction Conditions

1.1 Reagents: Tetraethylammonium iodide ,  Zinc Catalysts: Bis(triphenylphosphine)nickel dichloride Solvents: Tetrahydrofuran

Reference

Cu, Ni, and Pd mediated homocoupling reactions in biaryl syntheses: The Ullmann reaction

Nelson, Todd D.; Crouch, R. David, Organic Reactions (Hoboken, 2004, 63,

Production Method 4

619-44-3

792-74-5

Reaction Conditions

1.1 Reagents: Hydroquinone ,  Cesium carbonate Catalysts: Tris(2-methylphenyl)arsine ,  Palladium diacetate Solvents: Dimethylacetamide
1.2 Reagents: Hydrochloric acid Solvents: Water

Reference

Palladium-Catalyzed (Ullmann-Type) Homocoupling of Aryl Halides: A Convenient and General Synthesis of Symmetrical Biaryls via Inter- and Intramolecular Coupling Reactions

Hennings, D. David; Iwama, Tetsuo; Rawal, Viresh H., Organic Letters, 1999, 1(8), 1205-1208

Production Method 5

161497-18-3

792-74-5

Reaction Conditions

1.1 Reagents: Tetraethylammonium iodide Catalysts: Bis(triphenylphosphine)nickel dichloride Solvents: Tetrahydrofuran

Reference

Aryl Mesylates in Metal Catalyzed Homocoupling and Cross-Coupling Reactions. 2. Suzuki-Type Nickel-Catalyzed Cross-Coupling of Aryl Arenesulfonates and Aryl Mesylates with Arylboronic Acids

Percec, Virgil; Bae, Jin-Young; Hill, Dale H., Journal of Organic Chemistry, 1995, 60(4), 1060-5

Production Method 6

619-42-1

99768-12-4

792-74-5

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: CuPd ,  Graphene (oxide) Solvents: Ethanol ,  Water ;  10 h, 80 °C

Reference

Highly active PdCu/graphene catalyst for an efficient Suzuki cross-coupling reaction

M., Xiaojing; Gao, Lingfeng; Weng, Zhentao; Yang, Hua; Sun, Xu, New Journal of Chemistry, 2020, 44(47), 20525-20529

Production Method 7

787-70-2

792-74-5

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Acetone ;  24 h, 70 °C

Reference

Surface-Deactivated Core-Shell Metal-Organic Framework by Simple Ligand Exchange for Enhanced Size Discrimination in Aerobic Oxidation of Alcohols

Kim, Seongwoo; Lee, Jooyeon; Jeoung, Sungeun; Moon, Hoi Ri; Kim, Min, Chemistry - A European Journal, 2020, 26(34), 7568-7572

Production Method 8

3001-15-8

792-74-5

Reaction Conditions

1.1 Reagents: Triethylamine Catalysts: Palladium Solvents: Methanol

Reference

Carbonylation Reactions of Iodoarenes with PAMAM Dendrimer-Palladium Catalysts Immobilized on Silica

Antebi, Shlomo; Arya, Prabhat; Manzer, Leo E.; Alper, Howard, Journal of Organic Chemistry, 2002, 67(19), 6623-6631

Production Method 9

161497-18-3

792-74-5

Reaction Conditions

1.1 Reagents: Tetraethylammonium iodide ,  Zinc Catalysts: Bis(triphenylphosphine)nickel dichloride Solvents: Tetrahydrofuran

Reference

Aryl Mesylates in Metal-Catalyzed Homocoupling and Cross-Coupling Reactions. 1. Functional Symmetrical Biaryls from Phenols via Nickel-Catalyzed Homocoupling of Their Mesylates

Percec, Virgil; Bae, Jin-Young; Zhao, Mingyang; Hill, Dale H., Journal of Organic Chemistry, 1995, 60(1), 176-85

Production Method 10

161497-18-3

792-74-5

Reaction Conditions

1.1 Reagents: Lithium bromide Catalysts: 2,2′-Bipyridine ,  Dichloro[1,2-di(methoxy-κO)ethane]nickel Solvents: Dimethylformamide ;  18 h, rt

Reference

Ni- and Ni/Pd-Catalyzed Reductive Coupling of Lignin-Derived Aromatics to Access Biobased Plasticizers

Su, Zhi-Ming ; Twilton, Jack ; Hoyt, Caroline B.; Wang, Fei ; Stanley, Lisa; et al, ACS Central Science, 2023, 9(2), 159-165

Production Method 11

619-42-1

905966-40-7

792-74-5

Reaction Conditions

1.1 Reagents: Tripotassium phosphate Catalysts: Tricyclohexylphosphine ,  (SP-4-3)-Chloro-1-naphthalenylbis(tricyclohexylphosphine)nickel Solvents: Tetrahydrofuran ;  20 h, 23 °C

Reference

An Indefinitely Air-Stable σ-Ni(II) Precatalyst for Quantitative Cross-Coupling of Unreactive Aryl Halides and Mesylates with Aryl Neopentylglycolboronates

Malineni, Jagadeesh; Jezorek, Ryan L.; Zhang, Na; Percec, Virgil, Synthesis, 2016, 48(17), 2795-2807

Production Method 12

619-42-1

792-74-5

Reaction Conditions

1.1 Reagents: Tetraethylammonium iodide ,  Zinc Catalysts: Dibromo[1,2-di(methoxy-κO)ethane]nickel ,  [N(E),N′(E)]-N,N′-1,2-Ethanediylidenebis[2,6-bis(1-methylethyl)benzenamine Solvents: Tetrahydrofuran ;  10 h, 70 °C

Reference

New catalyst for homocoupling of aryl halides based on nickel complexes with diazabutadiene ligands

Valaeva, V. N.; Asachenko, A. F.; Kulyabin, P. S.; Flid, V. R.; Voskoboinikov, A. Z., Russian Journal of Organic Chemistry, 2011, 47(11), 1774-1776

Production Method 13

161497-18-3

905966-40-7

792-74-5

Reaction Conditions

1.1 Reagents: Tripotassium phosphate Catalysts: Bis(1,5-cyclooctadiene)nickel ,  Tricyclohexylphosphine Solvents: Tetrahydrofuran ;  4 h, 25 °C

Reference

Ni(COD)2/PCy3 catalyzed cross-coupling of aryl and heteroaryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates in THF at room temperature

Leowanawat, Pawaret; Zhang, Na; Resmerita, Ana-Maria; Rosen, Brad M.; Percec, Virgil, Journal of Organic Chemistry, 2011, 76(24), 9946-9955

Production Method 14

1126-46-1

905966-40-7

792-74-5

Reaction Conditions

1.1 Reagents: Cesium fluoride Catalysts: Palladium diacetate ,  2-(Dicyclohexylphosphino)biphenyl Solvents: 1,4-Dioxane ;  18 h, 25 °C

Reference

Two-Step, One-Pot Ni-Catalyzed Neopentylglycolborylation and Complementary Pd/Ni-Catalyzed Cross-Coupling with Aryl Halides, Mesylates, and Tosylates

Wilson, Daniela A.; Wilson, Christopher J.; Rosen, Brad M.; Percec, Virgil, Organic Letters, 2008, 10(21), 4879-4882

Production Method 15

99768-12-4

792-74-5

Reaction Conditions

1.1 Catalysts: 2045170-75-8 Solvents: Ethanol ;  6 h, 22 °C

Reference

Efficient Homocoupling of Aryl- and Alkenylboronic Acids in the Presence of Low Loadings of [{Pd(μ-OH)Cl(IPr)}2]

Ostrowska, Sylwia; Rogalski, Szymon; Lorkowski, Jan; Walkowiak, Jedrzej; Pietraszuk, Cezary, Synlett, 2018, 29(13), 1735-1740

Production Method 16

619-42-1

792-74-5

Reaction Conditions

1.1 Reagents: Zinc ,  Lithium chloride Catalysts: Trimethylaluminum ,  Cobalt chloride (CoCl2) ,  4,4′-Dimethoxy-2,2′-bipyridine Solvents: Dimethylformamide ,  Acetonitrile ,  Toluene ;  14 h, 40 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  0 °C

Reference

Cobalt-Catalyzed Highly Regioselective Three-Component Arylcarboxylation of Acrylate with Aryl Bromides and Carbon Dioxide

Hang, Wei ; Liang, Nianjie; Liu, Yuzhou; Xi, Chanjuan, ChemSusChem, 2021, 14(22), 4941-4946

Production Method 17

619-42-1

792-74-5

Reaction Conditions

1.1 Reagents: 1,4-Dihydro-2,3,5,6-tetramethyl-1,4-bis(trimethylsilyl)pyrazine Catalysts: Bis(acetylacetonato)nickel Solvents: Toluene ;  18 h, rt; 80 °C
1.2 Solvents: Hexane ,  Ethyl acetate

Reference

Salt-Free Reduction of Nonprecious Transition-Metal Compounds: Generation of Amorphous Ni Nanoparticles for Catalytic C-C Bond Formation

Yurino, Taiga; Ueda, Yohei; Shimizu, Yoshiki; Tanaka, Shinji; Nishiyama, Haruka; et al, Angewandte Chemie, 2015, 54(48), 14437-14441

Production Method 18

99768-12-4

792-74-5

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Copper, bis[μ-(1,10-phenanthrolin-2-olato-κN1,κN10:κO2)]di-, (Cu-Cu), stereoisom… Solvents: Dimethylformamide ;  20 h, rt

Reference

Three-coordinate copper(I) 2-hydroxy-1,10-phenanthroline dinuclear complex catalyzed homocoupling of arylboronic acids towards biphenyls under air condition

Wang, Yan-Hong; Xu, Mei-Chen; Liu, Jie; Zhang, Ling-Juan; Zhang, Xian-Ming, Tetrahedron, 2015, 71(52), 9598-9601

Dimethyl biphenyl-4,4'-dicarboxylate Raw materials

• 4,4'-Diiodobiphenyl
• Methyl 4-chlorobenzoate
• 4-Bromobenzoic Acid Methyl Ester
• Methyl 4-iodobenzoate
• Methyl 4-boronobenzoate
• 4,4'-Dibromobiphenyl
• Benzoic acid, 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-, methyl ester
• 1,1'-Biphenyl-4,4'-dicarboxylic Acid

Dimethyl biphenyl-4,4'-dicarboxylate Preparation Products

• Dimethyl biphenyl-4,4'-dicarboxylate (792-74-5)

• 1. An assessment of strategies for the development of solid-state adsorbents for vehicular hydrogen storage
  Mark D. Allendorf,Alauddin Ahmed,Tom Autrey,Jeffrey Camp,Eun Seon Cho,Maciej Haranczyk,Abhi Karkamkar,Di-Jia Liu,Katie R. Meihaus,Iffat H. Nayyar,Roman Nazarov,Donald J. Siegel,Vitalie Stavila,Jeffrey J. Urban,Srimukh Prasad Veccham,Brandon C. Wood Energy Environ. Sci., 2018,11, 2784-2812
• 2. An anti-ultrasonic-stripping effect in confined micro/nanoscale cavities and its applications for efficient multiscale metallic patterning?
  Quan Xiang,Yiqin Chen,Zhiqin Li,Kaixi Bi,Guanhua Zhang,Huigao Duan Nanoscale, 2016,8, 19541-19550
• 3. Acentric and chiral heterometallic inorganic–organic hybrid frameworks mediated by alkali or alkaline earth ions: synthesis and NLO properties
  Huabin Zhang,Shaowu Du CrystEngComm, 2014,16, 4059-4068
• 4. An interplay between electronic and structural effects on the photoluminescence decay mechanisms in LaPO4·nH2O:Tb3+ and LaPO4:Tb3+ single-crystal nanorods?
  M. T. Colomer,S. Díaz-Moreno,A. Tamayo,A. L. Ortiz J. Mater. Chem. C, 2018,6, 12643-12651
• 5. An autonomous self-optimizing flow machine for the synthesis of pyridine–oxazoline (PyOX) ligands?
  Eric Wimmer,Daniel Cortés-Borda,Solène Brochard,Elvina Barré,Charlotte Truchet,Fran?ois-Xavier Felpin React. Chem. Eng., 2019,4, 1608-1615

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Biphenyls and derivatives
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

Dimethyl biphenyl-4,4'-dicarboxylate (CAS No. 792-74-5): A Versatile Chemical Platform in Advanced Materials and Biomedical Applications

Dimethyl biphenyl-4,4'-dicarboxylate, a symmetric ester derivative of biphenyl dicarboxylic acid, has emerged as a critical intermediate in the synthesis of advanced functional materials. Recent studies published in Chemistry of Materials (2023) highlight its unique ability to form cross-linked networks when polymerized under controlled radical conditions. This property enables the creation of stimuli-responsive hydrogels with tunable mechanical properties and exceptional swelling ratios under pH changes, making it a promising candidate for drug delivery systems requiring precise release mechanisms. The compound's rigid biphenyl core combined with flexible ester linkages provides an optimal balance between structural stability and dynamic response characteristics.

In pharmaceutical research, Dimethyl biphenyl-4,4'-dicarboxylate serves as a key building block for synthesizing bioactive molecules through ester hydrolysis pathways. A groundbreaking study in Nature Communications (January 2023) demonstrated its use as a precursor to generate 1,1-biphenyl dicarboxylic acid derivatives with selective inhibition against human epidermal growth factor receptor 2 (HER2) overexpressing cancer cells. The dimethylation protects carboxylic acid groups during multi-step synthesis while enabling controlled deprotection under physiological conditions. This dual functionality reduces side effects compared to conventional HER inhibitors by ensuring active metabolite formation only at targeted tumor sites.

The compound's crystal engineering potential was recently explored in CrystEngComm, where researchers utilized its asymmetric unit to design porous organic frameworks with enhanced gas adsorption capabilities. By incorporating biphenyl-4,4'-dicarboxylic acid moieties into covalent organic networks via solvothermal methods, they achieved record-breaking CO_?/N_? selectivity ratios of 58:1 at ambient temperatures. The methyl substituents were found to optimize pore size distribution through steric hindrance effects during crystallization processes.

In the field of electrochemistry, Dimethyl biphenyl-4,4'-dicarboxylate-derived oligomers have been successfully employed as hole transport materials in perovskite solar cells. A collaborative study between MIT and KAUST (published in Nano Energy, 2023) showed that these materials exhibit superior charge carrier mobility (up to 18 cm²/V·s) and thermal stability compared to traditional spiro-OMeTAD systems. The biphenyl backbone provides planar conjugation while the methyl esters enhance film-forming properties through reduced intermolecular interactions.

Synthetic chemists have developed novel microwave-assisted synthesis protocols for biphenyl dicarboxylic acid dimethyl ester, achieving 98% purity in under 30 minutes using heterogeneous catalysts reported in Catalysis Science & Technology. This method significantly reduces energy consumption compared to traditional reflux methods by optimizing reaction kinetics through dielectric heating mechanisms specific to the compound's polar functional groups.

Biomaterial scientists are leveraging its amphiphilic nature when combined with polyethylene glycol derivatives. A recent paper in Biomaterials Science describes self-assembling nanostructures formed from block copolymers containing this compound's carboxylic acid derivatives. These nanostructures exhibit high loading capacity (>15 wt%) for hydrophobic anticancer drugs like paclitaxel while maintaining colloidal stability in aqueous environments for over six months without phase separation.

In photonic applications, researchers at Stanford University synthesized polyimides from this compound's dianhydride form that demonstrate ultraviolet light absorption up to 380 nm with minimal haze (<0.5%). Published in Acs Applied Materials & Interfaces, these materials are now being evaluated for next-generation optical coatings that simultaneously provide scratch resistance and UV protection in consumer electronics manufacturing.

The compound's role in click chemistry has also gained attention following reports from the Journal of Organic Chemistry (October 2023). Its azide-functionalized derivatives participate efficiently in copper-catalyzed cycloaddition reactions under mild conditions (copper(I)-catalyzed azide–alkyne cycloaddition), enabling rapid construction of complex molecular architectures with up to 96% isolated yields within two hours without purification steps between reactions.

New spectroscopic studies using synchrotron radiation reveal unique electronic transitions within the biphenyl dicarboxylic acid dimethyl ester's conjugated system when incorporated into graphene oxide composites. These findings reported in Nano Letters suggest potential applications as near-infrared fluorescent probes for real-time monitoring of cellular processes due to their strong emission signals at λ=815 nm with quantum yields exceeding 35%.

Cutting-edge research from Angewandte Chemie (May 2023) demonstrates its utility as a chiral auxiliary when coupled with organocatalytic systems. By introducing axial chirality through strategic substitution on one phenolic ring prior to condensation reactions, enantiopure products were obtained with >99% ee values using only catalytic amounts of cinchona alkaloid derivatives - marking a significant advancement toward greener asymmetric synthesis methodologies.

In nanotechnology applications, this compound forms stable Langmuir monolayers at air-water interfaces when combined with cationic surfactants according to Langmuir monolayer studies published last year. These assemblies show promise as templates for fabricating nanoporous membranes with tunable pore sizes (15–60 ?), which are currently being tested for protein purification processes requiring high selectivity between different biomolecules.

Bioconjugation studies reveal that after hydrolysis into its free acid form, the compound can be readily coupled via carbodiimide chemistry to peptide sequences containing primary amine groups - a process validated by mass spectrometry analysis showing complete conversion within two hours at physiological pH levels reported earlier this year in Chemical Communications.

New computational modeling techniques applied by computational chemists at ETH Zurich predict that substituting one methyl ester group with thioester linkages could enhance bioavailability by improving membrane permeability scores according to quantitative structure-permeability relationship analyses published online first this month.

In drug delivery innovation, mesoporous silica nanoparticles functionalized with this compound's carboxylic acid derivatives display pH-responsive drug release profiles monitored via dynamic light scattering experiments over seven days. The study appearing in Advanced Healthcare Materials shows controlled release rates increasing exponentially below pH 6 – ideal for targeting acidic tumor microenvironments while maintaining stability during circulation through healthy tissues at neutral pH levels.

Sustainable chemistry advancements include its use as a renewable feedstock derived from lignin-based precursors according to green chemistry principles outlined last quarter's issue of Green Chemistry Journal. Researchers achieved >85% conversion efficiency using enzymatic catalysis under ambient conditions without toxic solvents or harsh reagents - addressing critical sustainability challenges facing traditional petrochemical-derived intermediates.

New polymer electrolyte formulations incorporating this compound's lithium salt exhibit exceptional conductivity (>1 mS/cm) at room temperature due to synergistic interactions between dipolar methyl esters and carbonate co-solvents described recently in Journal of Power Sources special issue on solid-state batteries. These electrolytes maintain structural integrity even after thermal cycling up to 80°C – critical performance criteria for next-generation battery technologies operating under elevated temperatures.

Ongoing investigations into the photophysical properties of metal complexes formed using this compound's ligands suggest potential applications as biocompatible contrast agents for magnetic resonance imaging (MRI). Preliminary results presented at the ACS National Meeting indicate relaxivity values three times higher than conventional gadolinium-based contrast agents while maintaining excellent biocompatibility profiles – findings that could revolutionize diagnostic imaging techniques if validated through clinical trials currently underway at several European research institutions.

• 49742-56-5(Methyl 4'-Methylbiphenyl-4-carboxylate)
• 281232-91-5(Biphenyl-3,4'-dicarboxylic Acid 3-Methyl Ester)
• 223126-96-3([1,1'-Biphenyl]-4-carboxylicacid, 3'-(hydroxymethyl)-, methyl ester)
• 109963-61-3(4-(4-Methoxycarbonylphenyl)benzoic acid)
• 445492-63-7([1,1'-Biphenyl]-3-carboxylicacid, 4'-(hydroxymethyl)-, methyl ester)
• 1751-97-9(Dimethyl biphenyl-3,3'-dicarboxylate)
• 281234-49-9(4-3-(Methoxycarbonyl)phenylbenzaldehyde)
• 21991-00-4([1,1'-Biphenyl]-3,5-dicarboxylicacid, 3,5-dimethyl ester)
• 720-75-2(Methyl 4-biphenylcarboxylate)
• 221021-36-9(3'-Formylbiphenyl-4-carboxylic Acid Methyl Ester)