3217-47-8

Basic information

• Product Name: 2,3,5,6-TETRAFLUOROTEREPHTHALALDEHYDE
• Synonyms: 2,3,5,6-TETRAFLUOROTEREPHTHALALDEHYDE;Tetrafluoro-p-phthalaldehyde;Tetrafluoroterephthaldehyde;2,3,5,6-TETRAFLUOROTEREPHTHALALDEHY;2,3,5,6-Tetrafluorotelephtal aldehyde;1,4-Benzenedicarboxaldehyde, 2,3,5,6-tetrafluoro-
• CAS NO: 3217-47-8
• Molecular Formula: C₈H₂F₄O₂
• Molecular Weight: 206.0938928
• Mol File: 3217-47-8.mol

Chemical Properties

• Melting Point: 130-132℃
• Boiling Point: 252.566 °C at 760 mmHg
• Flash Point: 96.169 °C
• Appearance: /
• Density: 1.59 g/cm³
• Vapor Pressure: 0.019mmHg at 25°C
• Refractive Index: 1.525
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 2,3,5,6-TETRAFLUOROTEREPHTHALALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,5,6-TETRAFLUOROTEREPHTHALALDEHYDE(3217-47-8)
• EPA Substance Registry System: 2,3,5,6-TETRAFLUOROTEREPHTHALALDEHYDE(3217-47-8)

Safety Data

• Hazardous Substances Data: 3217-47-8(Hazardous Substances Data)

Usage

Uses

Used in the Synthesis of Covalent Organic Frameworks (COFs):
2,3,5,6-Tetrafluoroterephthalaldehyde is used as a building block for the synthesis of highly fluoro-substituted covalent organic frameworks (COFs). These COFs exhibit enhanced properties such as increased stability, chemical resistance, and thermal conductivity, which make them suitable for various applications in gas storage, separation, and catalysis.
Used in the Chemical Industry:
In the chemical industry, 2,3,5,6-tetrafluoroterephthalaldehyde is used as a precursor for the production of fluorinated polymers and other fluorinated materials. These materials are known for their exceptional performance characteristics, such as high durability, resistance to extreme temperatures, and low friction, making them ideal for use in various applications, including aerospace, automotive, and electronics.
Used in the Pharmaceutical Industry:
2,3,5,6-Tetrafluoroterephthalaldehyde can also be utilized in the pharmaceutical industry as a starting material for the synthesis of novel fluorinated drugs. The introduction of fluorine atoms into drug molecules can significantly improve their pharmacokinetic and pharmacodynamic properties, leading to enhanced drug efficacy and reduced side effects.
Used in the Electronics Industry:
In the electronics industry, 2,3,5,6-tetrafluoroterephthalaldehyde can be employed in the development of advanced materials for semiconductor devices, display technologies, and other electronic components. The fluorination of these materials can result in improved electrical properties, such as increased carrier mobility and reduced power consumption, which are crucial for the performance of modern electronic devices.

InChI:InChI=1/C8H2F4O2/c9-5-3(1-13)6(10)8(12)4(2-14)7(5)11/h1-2H

Upstream product

• 528869-11-6 1,2,4,5-tetrafluoro-3-(1,3-dioxol-2-yl)-6-formylbenzene 
• 528869-14-9 1,2,4,5-tetrafluoro-3-(5,5-dimethyl-1,3-dioxan-2-yl)-6-formylbenzene 
• 713144-57-1 1,4-bis(dichloromethyl)-2,3,5,6-tetrafluorobenzene 
• 306739-72-0 2,3,5,6-tetrafluoroterephthalaldehyde dimethylacetal 
• 719-32-4 tetrachloroterephthaloyl dichloride 
• 1835-49-0 tetrafluoroterephthalonitrile 
• 1897-41-2 2,3,5,6-tetrachloroterephthalonitrile 
• 1786-85-2 2,3,5,6-tetrachloro-1,4-benzenecarboxamide 
• 100-20-9 terephthaloyl chloride 
• 327-54-8 1,2,4,5-Tetrafluorobenzene 
• 19842-76-3 2,3,5,6-tetrafluorobenzaldehyde 
• 528869-06-9 1,2,4,5-tetrafluoro-3-(1,3-dioxol-2-yl)benzene 
• 528869-08-1 1,2,4,5-tetrafluoro-3-(5,5-dimethyl-1,3-dioxan-2-yl)benzene 
• 67-56-1 methanol 

Downstream Products

• 92339-07-6 2,3,5,6-tetrafluoro-1,4-benzenedimethanol 
• 713144-58-2 1,4-bis(4,5-diphenylimidazolyl-2-yl)tetrafluorobenzene 
• 713144-61-7 3,6-bis(4,5-diphenyl-2H-imidazolyl-2-ylidene)-1,2,4,5-tetrafluorocyclohexa-1,4-diene 
• 776-40-9 α,α’-dibromo-m-tetrafluoroxylene 
• 288627-04-3 [4-((diethoxyphosphoryl)methyl)-2,3,5,6-tetrafluorobenzyl]phosphonic acid diethyl ester 
• 327-54-8 1,2,4,5-Tetrafluorobenzene 
• 114649-17-1 1,4-bis(difluoromethyl)-2,3,5,6-tetrafluorobenzene 
• 713144-57-1 1,4-bis(dichloromethyl)-2,3,5,6-tetrafluorobenzene 
• 79538-03-7 2,3,5,6-tetrafluoro-4-methylbenzyl alcohol 
• 703-87-7 1,4-dimethyl-2,3,5,6-tetrafluorobenzene 
• 1311284-40-8 C₁₄H₂F₄N₄ 
• 1311284-50-0 2,2'-(2,3,5,6-tetrafluoro-1,4-phenylene)di(1,1,2-ethanetricarbonitrile) 
• 1311284-41-9 2,2'-(2,3,5,6-tetrafluoro-1,4-phenylene)di(1,1,2-ethenetricarbonitrile) 
• 1311284-43-1 2,2'-[(2,3,5,6-tetrafluoro-1,4-phenylene)bis{(1E)-3-[4-(dimethylamino)phenyl]-1-propen-1-yl-3-ylidene}]dimalononitrile 

Relevant articles and documents

α,α′-Diamino- p-tetrafluoroquinodimethane: Stability of One- And Two-Electron Oxidized Species and Fixation of Molecular Oxygen

Herein, we report the synthesis, characterization, and reactivity of α,α′-diamino-p-tetrafluoroquinodimethane, a p-tetrafluorophenylene-bridged monosubstituted carbene-based Thiele's hydrocarbon A. The compound exhibits a reversible two-step one-electron oxidation with a marginally stable radical cation state B. The in situ formation of the radical cation could be confirmed by electron paramagnetic resonance spectroscopy. Interestingly, α,α′-diamino-p-tetrafluoroquinodimethane fixates atmospheric oxygen to form a 16-membered peroxide-bridged macrocyclic compound C.

Diverse Proton-Conducting Nanotubes via a Tandem Macrocyclization and Assembly Strategy

Macrocycles that assemble into nanotubes exhibit emergent properties stemming from their low dimensionality, structural regularity, and distinct interior environments. We report a versatile strategy to synthesize diverse nanotube structures in a single, efficient reaction by using a conserved building block bearing a pyridine ring. Imine condensation of a 2,4,6-triphenylpyridine-based diamine with various aromatic dialdehydes yields chemically distinct pentagonal [5 + 5], hexagonal [3 + 3], and diamond-shaped [2 + 2] macrocycles depending on the substitution pattern of the aromatic dialdehyde monomer. Atomic force microscopy and in solvo X-ray diffraction demonstrate that protonation of the macrocycles under the mild conditions used for their synthesis drives assembly into high-aspect ratio nanotubes. Each of the pyridine-containing nanotube assemblies exhibited measurable proton conductivity by electrochemical impedance spectroscopy, with values as high as 10-3 S m-1 (90% R.H., 25 °C) that we attribute to differences in their internal pore sizes. This synthetic strategy represents a general method to access robust nanotube assemblies from a universal pyridine-containing monomer, which will enable systematic investigations of their emergent properties.

Reactions of Polyfluoroaromatic Organozinc Compounds with Oxalyl Chloride in DMF. Synthesis of Polyfluoroaromatic Aldehydes

Abstract: The reaction of polyfluoroaromatic organozinc compounds with oxalyl chloride in DMF proceeds involving the Vilsmeier–Haack reagent with the formation of polyfluoroaromatic aldehydes as the major products. The use of CuI makes it possible to incr

Synthesis of perfluoro[2.2]paracyclophane

(Chemical Equation Presented) A synthesis of perfluoro[2.2]paracyclophane has been sought ever since the partially fluorinated octafluoro[2.2]- paracyclophane (AF4) was prepared and its chemistry studied. This compound has now been prepared in 39% yield from the precursor, 1,4-bis(chlorodifluoromethyl) -2,3,5,6-tetrafluorobenzene by its reaction with Zn when heated in acetonitrile at 100°C. Two preparations of the precursor, first from 1,4-dicyano-2,3,5,6- tetrachlorobenzene and an improved method beginning from 1,2,4,5- tetrachlorobenzene, are also described as are key comparisons to our related synthesis of AF4.

Perfluoroparacyclophane and methods of synthesis and use thereof

A composition comprising perfluoro-[2,2]-paracyclophane dimer compound is disclosed. The synthesis reaction of the paracyclophane dimer from 1,4-bis(chlorodifluoromethane)-2,3,5,6-tetrafluorobenzene involves heating in the presence of a metal catalyst and a solvent. A perfluorinated paraxylylene coating formed from the perfluorinated paracyclophane dimer is also disclosed.

PROCESS FOR PREPARING TETRAFLUOROBENZENE CARBALDEHYDE ALKYL ACETAL

A process for preparing tetrafluorobenzene carbaldehyde alkyl acetal represented by the following formula (II), comprising reducing tetrafluorocyanobenzene represented by the following formula (I) with a metal catalyst containing a platinum group metal in the presence of an alkyl alcohol represented by R-OH (R is an alkyl group of 1 to 4 carbon atoms) and an acid; (I) wherein m is 1 or 2, n is 0 or 1, and m+n is 2, (II) wherein m and n are the same as those in the formula (I), and R is an alkyl group of 1 to 4 carbon atoms.

Definitive evidence for the contribution of biradical character in a closed-shell molecule, derivative of 1,4,-bis-(4,5-diphenylimidazol-2-ylidene)cyclohexa-2,5-diene

This study provides conclusive proof that the thermally excited open-shell state with biradical character is contributing to the ground state of a closed-shell molecule, tF-BDPI-2Y, where four hydrogen atoms at the central phenylene ring are substituted with four fluorine atoms of 1,4-bis-(4,5-diphenylimidazol-2-ylidene)cyclohexa-2,5-diene (BDPI-2Y). A small increase in the population of biradical species of tF-BDPI-2Y results in the formation of the dimer form by the radical recombination reaction. Controlling the equilibrium between a closed-shell diamagnetic-quinoid state and an open-shell paramagnetic-biradical state will provide significant progress in the field of π-conjugated delocalized biradical chemistry. Copyright

A new route to 2,3,5,6-tetrafluoroterephthal aldehyde and its chemical transformation

The title compound was prepared from commercial available and cheaper starting material terephthalolyl chloride by six-step reaction sequence in total 40% yield. Its chemical transformations were also studied.

Process for producing tetrafluorobenzenemethanols

The present invention relates to a process by a series of reactions using tetrafluorocyanobenzens as material for producing tetrafluorobenzenemethanols, tetrafluorobenzenecarbaldehyde dialkylacetals and tetrafluorobenzenecarbaldehydes in a high purity and a high yield which are useful as intermediates in the production of cyclopropanecarboxylic acid esters having insecticidal action, and also relates to a novel tetrafluorobenzenecarbaldehyde dimethylacetal.

Fluorinated molecules relevant to conducting polymer research

The synthesis of versatile fluorine compounds for conducting polymer research on fluorinated materials is presented. 1,2,4,5-Tetrafluorobenzene was converted to 1,2,4,5-tetrafluorobenzaldehyde (1) and protected as an acetal. This gave the acetals 1,2,4,5-tetrafluoro-3-(1,3-dioxol-2-yl)benzene (2a) and 1,2,4,5-tetrafluoro-3-(5,5-dimethyl-1,3-dioxan-2-yl)benzene (2b). Compounds 2a and 2b were converted into the semiprotected 2,3,5,6-tetrafluoroterephthaldehydes: 1,2,4,5-tetrafluoro-3-(1,3-dioxol-2-yl)-6-formylbenzene (3a) and 1,2,4,5- tetrafluoro-3-(5,5-dimethyl-1,3-dioxan-2-yl)-6-formylbenzene (3b). While 3a was easily deprotected to give 2,3,5,6-tetrafluoroterephthaldehyde (4) compound 3b proved very resilient to hydrolysis and gave a 1:1 mixture of 4 and 1,2,4,5-tetrafluoro-3,6-bis(5,5-dimethyl-1,3-dioxan-2-yl)benzene (5). Compound 4 was reduced to 1,2,4,5-tetrafluoro-3,6-dihydroxymethylbenzene (6) and converted into 1,2,4,5-tetrafluoro-3,6-dibromomethylbenzene (7). Compound 7 was finally converted into 1,2,4,5-tetrafluoro-3,6-bis(diethylphosponylmethyl)benzene (8). Compounds 4 and 8 are versatile fluorinated molecules that can be used to replace their hydrogen counterparts in many molecules and materials. To illustrate this compounds 4 and 8 were oligomerised to give partially fluorinated polyphenylenevinylene (9).