55676-76-1

Basic information

• Product Name: dimethyl [1,1'-biphenyl]-3,4'-dicarboxylate
• Synonyms: dimethyl [1,1'-biphenyl]-3,4'-dicarboxylate;3,4'-Biphenyldicarboxylic acid dimethyl ester;Biphenyl-3,4'-dicarboxylic acid dimethyl ester;(1,1'-Biphenyl)-3,4'-dicarboxylic acid, 3,4'-dimethyl ester;(1,1'-Biphenyl)-3,4'-dicarboxylic acid, dimethyl ester;Einecs 259-748-3;DiMethyl biphenyl-3,4'-dicarboxylate;methyl 3-(4-methoxycarbonylphenyl)benzoate
• CAS NO: 55676-76-1
• Molecular Formula: C₁₆H₁₄O₄
• Molecular Weight: 270.27996
• EINECS: 259-748-3
• Mol File: 55676-76-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: 95 °C
• Boiling Point: 416.8°Cat760mmHg
• Flash Point: 210.8°C
• Appearance: /
• Density: 1.172g/cm³
• CAS DataBase Reference: dimethyl [1,1'-biphenyl]-3,4'-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl [1,1'-biphenyl]-3,4'-dicarboxylate(55676-76-1)
• EPA Substance Registry System: dimethyl [1,1'-biphenyl]-3,4'-dicarboxylate(55676-76-1)

Safety Data

• Hazardous Substances Data: 55676-76-1(Hazardous Substances Data)

Usage

Uses

Dimethyl biphenyl-3,4''-dicarboxylate

Upstream product

• 905966-40-7 methyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoate 
• 618-91-7 methyl 3-iodo-benzoate 
• 618-89-3 methyl 3-bromobenzoate 
• 2905-65-9 methyl 3-chlorobenzoate 
• 19438-10-9 methyl 3-hydroxybenzoate 
• 161912-35-2 methyl 3-((methylsulfonyl)oxy)benzoate 
• 338396-38-6 methyl 3-((N,N-dimethylsulfamoyl)oxy)benzoate 

Relevant articles and documents

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.

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).