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

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

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

• 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 
• 131-11-3 phthalic 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.

METHOD FOR PRODUCING BIPHENYLTETRACARBOXYLIC ACID TETRAESTER AND PALLADIUM METAL COMPLEX FOR USE THEREIN

PROBLEM TO BE SOLVED: To provide a method for producing biphenyltetracarboxylic acid tetraester that has a high reaction rate of dimethylphthalate, and has a high selection rate of 3,3',4,4'-biphenyltetracarboxylic acid ester and a high catalyst turnover number (TON), and a catalyst used for the same. SOLUTION: The present invention provides a method using the following formula (2) or an isomeric compound thereof as a catalyst. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

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)].

METHOD FOR PRODUCING MULTISUBSTITUTED BIPHENYL COMPOUND AND SOLID CATALYST USED FOR THE SAME

PROBLEM TO BE SOLVED: To provide a method for producing a multisubstituted biphenyl compound in a high yield which easily recovers a catalyst, enables a high catalyst turnover number, a high catalyst turnover frequency and a high regioselectivity and can be applied to an intermolecular reaction without passing through a complicated step; and a solid catalyst to be used. SOLUTION: There is provided a method for producing a multisubstituted biphenyl compound represented by the formula (2), which comprises a step of coupling a substituted benzene compound represented by the formula (1) in the presence of a solid catalyst with a metal containing palladium immobilized on a carrier and a basic ligand. In addition, there is provided a solid catalyst for producing a multisubstituted biphenyl compound represented by the formula (2) which comprises a carrier, a metal containing palladium immobilized by the carrier and a basic ligand. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

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.

METHOD FOR PRODUCING BIPHENYLTETRACARBOXYLIC ACID TETRAESTER

Disclosed is a method for producing a biphenyltetracarboxylic acid ester by oxidative coupling a phthalic acid ester by using a catalyst comprising at least a palladium salt, a copper salt and a β-dicarbonyl compound in the presence of a molecular oxygen, wherein the β-dicarbonyl compound is supplied into a reaction mixture liquid intermittently at an interval of less than 30 minutes, or continuously. This method allows, in particular, the selective and economical production of an asymmetric biphenyltetracarboxylic acid tetraester such as 2,3,3′,4′-biphenyltetracarboxylic acid tetraester.

Process for production of 2, 3, 3', 4'-biphenyltetracarboxylic dianhydride

A process for producing 2,3,3′,4′-biphenyltetracarboxylic dianhydride (a-BPDA), comprising dehydrating 2,3,3′,4′-biphenyltetracarboxylic acid in an inert gas atmosphere under heating at 180 to 195° C is disclosed. This process produces high-purity a-BPDA which is suitable for production of a polyimide.

Preparation of 2,3,3',4' -biphenyltetracarboxylic acid tetraester

2,3,3′,4′-Biphenyltetracarboxylic acid tetraester is predominantly produced by a process in which a phthalic acid diester is subjected to oxidative-coupling reaction in the presence of molecular oxygen and a catalyst comprising a rhodium-containing compound,.

Process for production of biphenyltetracarboxylic acid tetraesters

A production process, especially a continuous production process, for a biphenyltetracarboxylic acid tetraester characterized by carrying out, in parallel, a step of preliminarily mixing a phthalic acid diester and a palladium compound-containing catalyst to prepare a starting mixture, a step of continuously or intermittently supplying the starting mixture to a reactor, a step of conducting oxidative dimerization reaction of the phthalic acid diester in a temperature range of from 140° C. and lower than 250° C. while supplying molecular oxygen to the reactor to form a reaction mixture in the reactor, and a step of continuously or intermittently removing a portion of the reaction mixture from the reactor. Preferably, the palladium compound-containing catalyst in the starting mixture is dissolved in the phthalic acid diester, the palladium compound-containing catalyst comprises a palladium compound, a bidentate ligand and a copper compound, the reactor consists of a plurality of serially connected reactors and a carboxylic acid is also continuously or intermittently supplied to the reactor.