652-36-8

Basic information

• Product Name: Tetrafluoroterephthalic acid
• Synonyms: 1,4-Benzenedicarboxylic acid, 2,3,5,6-tetrafluoro-;RARECHEM AL BO 0018;TETRAFLUOROBENZENE-1,4-DICARBOXYLIC ACID;TETRAFLUOROTEREPHTHALIC ACID;2,3,5,6-TETRAFLUOROTEREPHTHALIC ACID;2,3,5,6-TETRAFLUORO-1,4-BENZENEDICARBOXYLIC ACID;2,3,5,6-Tetrafluoroterephthlonic Acid;Tetrafluoroterephthalic acid 97%
• CAS NO: 652-36-8
• Molecular Formula: C₈H₂F₄O₄
• Molecular Weight: 238.09
• EINECS: 211-489-7
• Mol File: 652-36-8.mol
• Article Data: 8

Chemical Properties

• Melting Point: 275-277 °C (dec.)(lit.)
• Boiling Point: 337.9 °C at 760 mmHg
• Flash Point: 158.1 °C
• Appearance: white crystals
• Density: 1.812 g/cm³
• Vapor Pressure: 3.98E-05mmHg at 25°C
• Refractive Index: 1.522
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 0.95±0.10(Predicted)
• Water Solubility: very faint turbidity in hot Water
• CAS DataBase Reference: Tetrafluoroterephthalic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Tetrafluoroterephthalic acid(652-36-8)
• EPA Substance Registry System: Tetrafluoroterephthalic acid(652-36-8)

Safety Data

• Hazard Codes: Xi,C
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: CORROSIVE
• Hazardous Substances Data: 652-36-8(Hazardous Substances Data)

Usage

Uses

Used in Chemical Industry:
Tetrafluoroterephthalic acid is used as a key compound for the preparation of zinc/nickel/copper imidazolylpyridinone tetrafluoroterephthalate. Its chemical properties, including its white powder form, contribute to the effectiveness and stability of the final product in this application.
Used in Material Science:
Tetrafluoroterephthalic acid is utilized as a building block in the synthesis of advanced materials, such as polymers and composites, due to its unique chemical structure and properties. This application takes advantage of its ability to form stable and functional materials with desirable characteristics.
Used in Electronics:
In the electronics industry, Tetrafluoroterephthalic acid is employed as a component in the development of high-performance electronic devices and components. Its properties make it suitable for use in the creation of materials with specific electrical and thermal properties, enhancing the performance and reliability of electronic systems.
Used in Pharmaceutical Industry:
Tetrafluoroterephthalic acid serves as an intermediate in the synthesis of various pharmaceutical compounds, including drugs and drug delivery systems. Its unique chemical properties allow for the development of novel therapeutic agents with improved efficacy and reduced side effects.
Used in Environmental Applications:
Tetrafluoroterephthalic acid is also used in environmental applications, such as the treatment of wastewater and the removal of pollutants. Its chemical properties enable it to effectively bind and remove contaminants, contributing to a cleaner and safer environment.

InChI:InChI=1/C8H2F4O4/c9-3-1(7(13)14)4(10)6(12)2(5(3)11)8(15)16/h(H,13,14)(H,15,16)

Upstream product

• 392-56-3 Hexafluorobenzene 
• 536-74-3 phenylacetylene 
• 140455-18-1 heptafluoro-p-toluyl chloride 
• 5216-22-8 perfluoro-4-methylbenzoic acid 
• 950-71-0 1,4-(CONH₂)2-C₆F₄ 
• 776-40-9 α,α’-dibromo-m-tetrafluoroxylene 
• 16252-45-2 ((perfluoro-1,4-phenylene)bis(ethyne-2,1-diyl))dibenzene 
• 117338-23-5 2,3,5,6-tetrafluoro-4-trifluoromethyl-benzoyl fluoride 
• 651-89-8 1,2,4,5-tetrafluoro-3,6-bis-trifluoromethyl-benzene 
• 1554-48-9 1,2,4,5-tetrafluoro-3,6-bis[(E)-prop-1-en-1-yl]benzene 
• 1554-48-9 1,2,4,5-Tetrafluor-3--6--benzol 
• 1554-48-9 1,2,4,5-Tetrafluor-3.6-bis--benzol 
• 727-55-9 dimethyl 2,3,5,6-tetrafluoroterephthalate 
• 1897-41-2 2,3,5,6-tetrachloroterephthalonitrile 

Downstream Products

• 652-18-6 2,3,5,6-tetrafluorobenzoic acid 
• 963-46-2 diethoxy 2,3,5,6-tetrafluoroterephthalate 
• 54431-83-3 N,N,N'N'-tetraethyl-2,3,5,6-tetrafluorobenzene-1,4-dicarboxamide 
• 954-15-4 2,3,5,6-tetrafluoro-4-(methoxycarbonyl)benzoic acid 
• 107900-84-5 2,3,5,6-tetrafluoro-4-(hydroxymethyl)benzoic acid 
• 92339-07-6 2,3,5,6-tetrafluoro-1,4-benzenedimethanol 

Relevant articles and documents

Extending the series of p-substituted tetrafluorobenzoic acids: synthesis, properties and structure

The synthesis of the derivatives of p-aminotetrafluorobenzoic acid, p-H2NC6F4CO2H (2b), by hydrolysis, acylation or interaction with aldehydes was developed giving H2NC6F4CO2K (2a), C6F5C(O)N(H)C6F4CO2Et (3) and (E)-ArCH[dbnd]NC6F4CO2Et (4–11). The chemical derivatization of tetrafluoroterephthalic acid, p-HO2CC6F4CO2H (12), by hydrolysis, etherification and reduction was performed giving a number of symmetrical X(O)CC6F4C(O)X (13–15; X?=?Cl, NEt2, OMe) or unsymmetrical YC6F4CO2Me (15a–b, 16, 18–21; Y?=?CO2K, CO2H, CH2OH, C(O)Cl, C(O)C6H3(i-Pr)2, CO2CH2C6F4CO2Me, CO2C6H4Bu-t), HOCH2C6F4CO2H (17), [MeO2CC6F4]2Y (22, 23; Y?=?OCH2CH2O, N(H)C6H4N(H)) compounds. All substances were thoroughly investigated by spectroscopic methods (multinuclear NMR and IR spectroscopy, mass-spectrometry). The molecular structures of p-H2NC6F4CO2Et (2) and p-HO2CC6F4CO2Me (15b) have been determined by X-ray diffraction analysis.

CARBOXYLATION CATALYSTS

The use of a complex of the form Z—M—OR in the carboxylation of a substrate is described. The group Z is a two-electron donor ligand, M is a metal and OR is selected from the group consisting of OH, alkoxy and aryloxy. The substrate may be carboxylated at a C—H or N—H bond. The metal M may be copper, silver or gold. The two-electron donor ligand may be a phosphine, a carbene or a phosphite ligand. Also described are methods of manufacture of the complexes and methods for preparing isotopically labelled caboxylic acids and carboxylic acid derivatives.

Optimized synthesis of tetrafluoroterephthalic acid: A versatile linking ligand for the construction of new coordination polymers and metal-organic frameworks

Pure 2,3,5,6-tetrafluoroterephthalic acid (H2tfBDC) is obtained in high yields (95%) by reacting 1,2,4,5-tetrafluorobenzene with a surplus (>2 equiv) of n-butyllithium in tetrahydrofuran (THF) and subsequent carbonation with CO2 without any extensive purification procedure. A single crystal X-ray structure analysis of H2tfBDC (1) confirms former data obtained for a deuterated sample (P1, Z= 1). Recrystallization from water/acetone leads to single crystals of H2tfBDC · 2H2O (2, P21/c, Z= 2), where an extensive hydrogen bonding network is found. By reacting H2tfBDC with an aqueous ammonia solution, single crystals of (NH4)2tfBDC (3, C2/m, Z= 2) are obtained. 3 is thermally stable up to 250 °C and shows an enhanced solubility in water compared to H2tfBDC. Monosubstituted 2,3,5,6-tetrafluorobenzoic acid (H2tfBC, 4) is obtained by reacting 1,2,4,5-tetrafluorobenzene with stoichiometric amounts (1 equiv) of n-butyllithium in THF. Its crystal structure (Fdd2, Z= 16) shows dimeric units as characteristic structural feature.

Carboxylation of C-H bonds using N -heterocyclic carbene gold(I) complexes

A highly efficient [(NHC)AuI]-based (NHC = N-heterocyclic carbene) catalytic system for the carboxylation of aromatic and heteroaromatic C-H bonds was developed. The significant base strength of the Au-OH species is at the origin of the activation process and permits the facile functionalization of C-H bonds without the use of other organometallic reagents.

Carboxylation of N-H/C-H bonds using n-heterocyclic carbene copper(I) complexes

Greenhouse gas makes good: A simple copper-mediated protocol has been developed where N-H or C-H bonds can be directly functionalized using an easily prepared catalyst. The novel [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene] copper(I) hydroxide, [Cu(IPr)(OH)], permits the facile activation and carboxylation of N-H and C-H bonds with pKavalues of less than 27.7 (see scheme).

METHOD FOR PRODUCING 4-METHYL-2,3,5,6-TETRAFLUOROBENZYL ALCOHOL

A process for producing 4-methyl-2,3,5,6-tetrafluorobenzyl alcohol comprising the following steps (A) to (D): Step (A): a step for fluorinating 2,3,5,6-tetrachloroterephthaloyl dichloride, Step (B): a step for reducing the product obtained in step (A), Step (C): a step for chlorinating the product obtained in step (B), Step (D): a step for hydrogenating the product obtained in step (C).

Aryl or heteroaryl amides of tetrahydronaphthalene, chroman, thichroman and 1,2,3,4-tetrahydroquinolinecarboxlic acids, having an electron withdrawing substituent in the aromatic or heteroaromatic moiety, having retinoid-like biological activity

Compounds of the formula wherein the symbols have the meaning defined in the specification have retinoid-like biological activity.

REACTION OF PERFLUORINATED METHYL- AND ALKENYLBENZENES WITH INORGANIC OXIDES IN THE PRESENCE OF ANTIMONY PENTAFLUORIDE

A study was carried out on the reaction of perfluorinated toluene, m-xylene, p-xylene, mesitylene, and m-(1-propenyl)toluene with inorganic oxides in the presence of antimony pentafluoride.Depending on the reaction conditions, polyfluorinated acids resulting from the consecutive conversion of trifluoromethyl groups into carboxylic acid groups are obtained after hydrolysis of the reaction mixtures.