36978-36-6

Basic information

• Product Name: BIPHENYL-2,3,3',4'-TETRACARBOXYLIC ACID TETRAMETHYL ESTER
• Synonyms: BIPHENYL-2,3,3',4'-TETRACARBOXYLIC ACID TETRAMETHYL ESTER;2,3,3',4'-Biphenyltetracarboxylic acid tetramethyl ester
• CAS NO: 36978-36-6
• Molecular Formula: C₂₀H₁₈O₈
• Molecular Weight: 386.35212
• Mol File: 36978-36-6.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 504.1±50.0 °C(Predicted)
• Appearance: /
• Density: 1.261±0.06 g/cm3(Predicted)
• CAS DataBase Reference: BIPHENYL-2,3,3',4'-TETRACARBOXYLIC ACID TETRAMETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: BIPHENYL-2,3,3',4'-TETRACARBOXYLIC ACID TETRAMETHYL ESTER(36978-36-6)
• EPA Substance Registry System: BIPHENYL-2,3,3',4'-TETRACARBOXYLIC ACID TETRAMETHYL ESTER(36978-36-6)

Safety Data

• Hazardous Substances Data: 36978-36-6(Hazardous Substances Data)

Usage

General Description

Biphenyl-2,3,3',4'-tetracarboxylic acid tetramethyl ester is a chemical compound commonly used as a building block for the synthesis of various organic compounds. It is a derivative of biphenyl, a type of aromatic hydrocarbon, and contains four carboxylic acid groups, which make it useful for the formation of complex organic molecules. The tetramethyl ester group further enhances its stability and reactivity, making it an important intermediate in the production of pharmaceuticals, agrochemicals, and materials. BIPHENYL-2,3,3',4'-TETRACARBOXYLIC ACID TETRAMETHYL ESTER is primarily used in organic synthesis and research, and its unique structure and properties make it valuable in the development of new chemical products and materials.

Upstream product

• 131-11-3 phthalic acid dimethyl ester 
• 87639-57-4 4-bromophthalic Acid Dimethyl Ester 
• 102928-38-1 dimethyl 3-iodophthalate 
• 67-56-1 methanol 
• 88-99-3 benzene-1,2-dicarboxylic acid 

Downstream Products

• 36978-40-2 2,3,3′,4′-biphenyl tetracarboxylic dianhydride 

Relevant articles and documents

Pd/Cu-Catalyzed Dehydrogenative Coupling of Dimethyl Phthalate: Synchrotron Radiation Sheds Light on the Cu Cycle Mechanism

Pd/Cu-catalyzed dehydrogenative coupling of dimethyl phthalate is an important industrial process for the production of aromatic polyimide precursors. Nonetheless, the detailed mechanism of the Cu cycle has remained unclear. The present study describes the detailed mechanism of the Cu cycle in the [Pd(OAc)2]/Cu(OAc)2/1,10-phenanthroline (phen) system. The solution-phase X-ray absorption fine structure analysis of the catalyst solutions and the FEFF fitting as well as the evaluation of the catalytic and stoichiometric reactions reveal the following observations: (i) the major intermediate in the catalytic cycle is a mononuclear divalent [Cu(OAc)2]·2H2O species, (ii) coordination of the phen ligand to the Cu catalyst significantly inhibits the catalytic activity, (iii) 2 equiv of Cu(OAc)2·H2O oxidizes the zerovalent "Pd(phen)" species to divalent [Pd(OAc)2(phen)], and (iv) the divalent [Cu(OAc)2]2·2AcOH species is regenerated by the treatment of monovalent Cu(OAc) with AcOH in air.

Mechanistic Insights on Pd/Cu-Catalyzed Dehydrogenative Coupling of Dimethyl Phthalate

Despite its industrial importance, very limited mechanistic information on the dehydrogenative coupling of dimethyl phthalate has been reported. Herein we report the detailed mechanism for dehydrogenative coupling of dimethyl phthalate catalyzed by [Pd(OAc)2]/[Cu(OAc)2]/1,10-phenanthroline·H2O (phen·H2O). The solution-phase analysis of the catalytic system by XANES shows the active species to be Pd(II), and EXAFS supports the formation of an (acetato)(dimethyl phthalyl)(phen)palladium(II) complex from [Pd(OAc)2]. A formation pathway of tetramethyl 3,3′,4,4′-biphenyltetracarboxylate via disproportionation of independently prepared [Pd(OAc){C6H3(CO2Me)2-3,4}(phen)] is observed with regeneration of [Pd(OAc)2(phen)].

Preparation method for biphenyltetracarboxylic dianhydride mixture

The invention relates to a preparation method for a biphenyltetracarboxylic dianhydride mixture. The preparation method comprises the following steps: with phthalic acid as a starting raw material, carrying out an electrophilic substitution reaction so as to produce a phthalic acid derivative; then subjecting the derivative to esterification so as to produce phthalate; further catalyzing phthalate and carrying out a coupling reaction so as to produce a biphenyl tetraformate mixture; and finally, successively carrying out saponification and acidification so as to produce the product biphenyltetracarboxylic dianhydride mixture. The method provided by the invention uses cheap and easily phthalic acid as the starting raw material and is a novel low-cost easily-operatable environment-friendly production method for biphenyltetracarboxylic dianhydride; moreover, isomeric compounds of all the biphenyltetracarboxylic dianhydride are synthesized at one time in the invention, so efficiency is improved and the cost is reduced.