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

Description

BIPHENYL-2,3,3',4'-TETRACARBOXYLIC ACID TETRAMETHYL ESTER is a chemical compound that serves as a building block for the synthesis of various organic compounds. It is a biphenyl derivative, an aromatic hydrocarbon, featuring four carboxylic acid groups. The tetramethyl ester group attached to it enhances its stability and reactivity, making it a crucial intermediate in the production of pharmaceuticals, agrochemicals, and materials. Its unique structure and properties contribute to its value in developing new chemical products and materials.

Uses

Used in Organic Synthesis:
BIPHENYL-2,3,3',4'-TETRACARBOXYLIC ACID TETRAMETHYL ESTER is used as a building block for the creation of complex organic molecules due to its carboxylic acid groups and tetramethyl ester functionality.
Used in Pharmaceutical Production:
In the pharmaceutical industry, BIPHENYL-2,3,3',4'-TETRACARBOXYLIC ACID TETRAMETHYL ESTER is used as an intermediate for the synthesis of various drugs, leveraging its reactivity and stability to form medicinal compounds.
Used in Agrochemical Development:
BIPHENYL-2,3,3',4'-TETRACARBOXYLIC ACID TETRAMETHYL ESTER is utilized as a key component in the development of agrochemicals, contributing to the creation of effective pesticides and other agricultural products.
Used in Material Science:
In the field of material science, BIPHENYL-2,3,3',4'-TETRACARBOXYLIC ACID TETRAMETHYL ESTER is employed for the development of new materials, taking advantage of its structural properties to enhance material performance.
Used in Research:
BIPHENYL-2,3,3',4'-TETRACARBOXYLIC ACID TETRAMETHYL ESTER is also used in research settings to explore its potential applications and to understand its chemical behavior, further expanding its utility in various scientific and industrial applications.

Upstream product

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

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.