55676-77-2

Basic information

• Product Name: dimethyl [1,1'-biphenyl]-2,4'-dicarboxylate
• Synonyms: dimethyl [1,1'-biphenyl]-2,4'-dicarboxylate;2,4'-Biphenyldicarboxylic acid dimethyl ester;Biphenyl-2,4'-dicarboxylic acid dimethyl ester;(1,1'-Biphenyl)-2,4'-dicarboxylic acid, 2,4'-dimethyl ester;(1,1'-Biphenyl)-2,4'-dicarboxylic acid, dimethyl ester;Einecs 259-749-9;2,4'-Biphenyl-dicarboxylic acid
• CAS NO: 55676-77-2
• Molecular Formula: C₁₆H₁₄O₄
• Molecular Weight: 270.27996
• EINECS: 259-749-9
• Mol File: 55676-77-2.mol

Chemical Properties

• Boiling Point: 416.2 °C at 760 mmHg
• Flash Point: 210.4 °C
• Appearance: /
• Density: 1.172 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: dimethyl [1,1'-biphenyl]-2,4'-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl [1,1'-biphenyl]-2,4'-dicarboxylate(55676-77-2)
• EPA Substance Registry System: dimethyl [1,1'-biphenyl]-2,4'-dicarboxylate(55676-77-2)

Safety Data

• Hazardous Substances Data: 55676-77-2(Hazardous Substances Data)

Usage

Uses

Used in Polymer Production:
Dimethyl [1,1'-biphenyl]-2,4'-dicarboxylate is used as a monomer in the synthesis of various polymeric materials with high heat resistance, chemical stability, and electrical properties. It contributes to the development of advanced materials with excellent thermal and mechanical properties.
Used in Electronic Devices:
Dimethyl [1,1'-biphenyl]-2,4'-dicarboxylate is used as a key component in the production of electronic devices, such as liquid crystal displays and optical films, due to its high heat resistance and electrical properties. It enhances the performance and reliability of these devices.
Used in Fiber Optic Cables:
In the telecommunications industry, dimethyl [1,1'-biphenyl]-2,4'-dicarboxylate is used in the manufacturing of fiber optic cables. Its high heat resistance and chemical stability make it suitable for use in cables that require high-performance characteristics.
Used in High-Temperature Engineering Applications:
Dimethyl [1,1'-biphenyl]-2,4'-dicarboxylate is used in high-temperature engineering applications, where materials with excellent thermal and mechanical properties are required. It contributes to the development of advanced materials that can withstand extreme temperatures and harsh environments.

Upstream product

• 610-97-9 o-iodo-methyl-benzoic acid 
• 619-44-3 methyl 4-iodobenzoate 
• 67-56-1 methanol 
• 93-58-3 benzoic acid methyl ester 
• 905966-40-7 methyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoate 
• 95667-98-4 methyl 2-((methylsulfonyl)oxy)benzoate 
• 119-36-8 methyl salicylate 
• 338396-06-8 methyl 4-((N, N-dimethylsulfamoyl)oxy)benzoate 
• 161497-18-3 methyl 4-(methanesulfonyloxy)benzoate 
• 68061-82-5 methyl 2-(methyl(nitroso)amino)benzoate 
• 610-96-8 methyl chlorobenzoate 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 99768-12-4 4-methoxycarbonylphenylboronic acid 

Relevant articles and documents

Iodobenzene-Catalyzed Synthesis of Phenanthridinones via Oxidative C-H Amidation

We report a novel synthesis of phenanthridinones from N-methoxybenzamides using an oxidative C-H amidation reaction at room temperature in open air with modest to excellent yields. This method demonstrated unprecedented substrate scope. In particular, it solved the long-standing challenge in the synthesis of phenanthridinones with sterically demanding substitutions.

An Indefinitely Air-Stable σ-NiII Precatalyst for Quantitative Cross-Coupling of Unreactive Aryl Halides and Mesylates with Aryl Neopentylglycolboronates

Three classes of Ni precatalysts based on π-NiII, π-Ni0 and σ-NiII complexes have been elaborated and employed in different laboratories for the functionalization and cross-coupling of otherwise inert aryl C-O, C-Cl, and C-F electrophiles. Various Ni precatalysts, ligands, boron sources, and reaction conditions that were developed in various research groups, necessitated the selection of the most suitable conditions for desired cross-coupling partners. Here a universal, bench-stable, easily prepared NiIICl(1-naphthyl)(PCy3)2/PCy3 σ-complex, for efficient and quantitative cross-coupling of aryl chlorides, bromides, iodides, mesylates, and fluorides with aryl neopentylglycolboronates is reported. This precatalyst will most probably help to advance the applications of Ni catalysis in organic, supramolecular, and macromolecular synthesis and will provide an easier access to the selection of reaction conditions for various transformations.

Structural elucidation of thermolysis products of methyl N-methyl-N-nitrosoanthranilate

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Trans -chloro(1-naphthyl)bis(triphenylphosphine)nickel(II)/PCy3 catalyzed cross-coupling of aryl and heteroaryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates at room temperature

trans-Chloro(1-naphthyl)bis(triphenylphosphine)nickel(II) complex/PCy 3 system has been successfully applied as catalyst for the Suzuki-Miyaura cross-coupling of aryl and heteroaryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates in THF at room temperature. This cross-coupling reaction tolerates various functional groups, including keto, imino, ester, ether, and cyano. Together with the nickel-catalyzed, one-pot, two-step neopentylglycolborylation, this bench stable and inexpensive Ni(II)-based catalyst can be utilized as an alternative to Ni(COD) 2/PCy3 to provide an inexpensive, robust, and convenient synthesis of biaryl and heterobiaryl compounds.

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

Reaction conditions for the Ni(COD)2/PCy3 catalyzed cross-coupling of aryl neopentylglycolboronates with aryl mesylates were developed. By using optimized reaction conditions, Ni(COD)2/PCy 3 was shown to be a versatile catalyst for the cross-coupling of a diversity of aryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates containing both electron-donating and electron-withdrawing substituents in their para, ortho, and meta positions in THF at room temperature. This Ni-catalyzed cross-coupling of aryl neopentylglycolboronates is also effective for the synthesis of heterobiaryls and biaryls containing electrophilic functionalities sensitive to organolithium and organomagnesium derivatives. In combination with the recently developed Nicatalyzed neopentylglycolborylation, all Ni-catalyzed routes to functional biaryls and heterobiaryls are now easily accessible (Figure presented).

Palladium-catalyzed reactions of arylindium reagents prepared directly from aryl iodides and indium metal

(Chemical Equation Presented) Treatment of aryl iodides with indium metal in the presence of lithium chloride leads to the formation of an organoindium reagent capable of participating in cross-coupling reactions under transition-metal catalysis. Combination with aryl halides in the presence of 5 mol % Cl2Pd(dppf) furnishes biaryl compounds in good yields; similarly, reaction with acyl halides or allylic acetates/carbonates in the presence of 5-10 mol % palladium catalyst leads to arylketones and allylic substitution products, respectively, in moderate yields. The reactions are tolerant of the presence of protic solvents, and ～85% of the indium metal employed can be recovered by reduction of the residual indium salts with zinc(0).

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.

Ultrasound-Promoted Synthesis of Arylzinc Compounds Using Zinc Powder and Their Application to Palladium(0)-Catalyzed Synthesis of Multifunctional Biaryls

Arylzinc compounds containing electron-withdrawing groups such as CO2CH3, CON(CH3)2, CN, Br, Cl, or CF3 at ortho position were prepared readily by the ultrasound-promoted reaction of aryl iodides with zinc powder, which were applied to palladium(0)-catalyzed cross-coupling with aryl halides to afford unsymmetrical and multifunctional biaryls in good yields.