19842-76-3

Usage

Uses

Used in Chemical Synthesis:
2,3,5,6-Tetrafluorobenzaldehyde is used as a key intermediate in the synthesis of various organic compounds, particularly those with fluorinated structures. Its unique properties and reactivity make it a valuable building block for creating complex molecules with specific applications in different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,3,5,6-tetrafluorobenzaldehyde is used as a starting material for the development of new drugs with potential therapeutic applications. Its fluorinated structure can enhance the pharmacokinetic and pharmacodynamic properties of the resulting compounds, leading to improved efficacy and selectivity.
Used in Material Science:
2,3,5,6-Tetrafluorobenzaldehyde can be utilized in the development of advanced materials with specific properties, such as high thermal stability, chemical resistance, and low refractive index. These materials can find applications in various fields, including electronics, aerospace, and automotive industries.
Used in Agrochemical Industry:
The agrochemical industry can benefit from the use of 2,3,5,6-tetrafluorobenzaldehyde as a precursor for the synthesis of novel pesticides, herbicides, and other agrochemicals. The introduction of fluorine atoms can improve the biological activity, selectivity, and environmental persistence of these compounds.

Upstream product

• 327-54-8 1,2,4,5-Tetrafluorobenzene 
• 109-94-4 formic acid ethyl ester 
• 67-56-1 methanol 
• 5216-17-1 2,3,5,6-tetrafluorobenzonitrile 
• 306739-71-9 2,3,5,6-tetrafluorobenzaldehyde dimethylacetal 
• 95-50-1 1,2-dichloro-benzene 
• 598-54-9 copper (I) acetate 
• 617-86-7 triethylsilane 
• 653-37-2 perfluorobenzaldehyde 
• 107535-73-9 2,3,5,6-tetrafluorobenzoic acid chloride 
• 181183-63-1 2,3,5,6-C₆F₄HCCl₃ 

Downstream Products

• 158388-62-6 Benzyl-[1-(2,3,5,6-tetrafluoro-phenyl)-meth-(E)-ylidene]-amine 
• 157042-73-4 (4S,5R)-5-(2,3,5,6-tetrafluorophenyl)-2-oxazoline-4-(N,N-dimethyl)carboxamide 
• 4084-38-2 (2,3,5,6-tetrafluorophenyl)methanol 
• 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 
• 857722-22-6 (E)-3-(2,3,5,6-Tetrafluoro-phenyl)-propenal 
• 857722-10-2 1,2,4,5-Tetrafluoro-3-((1E,3E)-4-phenyl-buta-1,3-dienyl)-benzene 
• 776-40-9 α,α’-dibromo-m-tetrafluoroxylene 
• 92339-07-6 2,3,5,6-tetrafluoro-1,4-benzenedimethanol 
• 3217-47-8 2,3,5,6-tetrafluoroterephthalaldehyde 
• 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 
• 288627-04-3 [4-((diethoxyphosphoryl)methyl)-2,3,5,6-tetrafluorobenzyl]phosphonic acid diethyl ester 

Relevant academic research and scientific papers

Synthetic method of transfluthrin intermediate

The invention discloses a synthetic method of a transfluthrin intermediate, and belongs to the technical field of chemical synthesis, the synthetic method is characterized by comprising the following steps: (1) taking 2, 3, 5, 6-tetrafluorobenzene as a raw material, and reacting with carbon tetrachloride to obtain 2, 3, 5, 6-tetrafluorotrichloromethyl benzene; (2) under the action of a composite catalyst, carrying out catalytic hydrolysis on the 2, 3, 5, 6-tetrafluorotrichloromethyl benzene to obtain 2, 3, 5, 6-tetrafluorobenzoyl chloride; (3) under the action of a catalyst, the 2, 3, 5, 6-tetrafluorobenzoyl chloride and hydrogen are subjected to a Rosenmonde reduction reaction, and 2, 3, 5, 6-tetrafluorobenzaldehyde is obtained; (4) carrying out catalytic hydrogenation reaction on the 2, 3, 5, 6-tetrafluorobenzaldehyde and hydrogen to obtain 2, 3, 5, 6-tetrafluorobenzyl alcohol; the method has the advantages of simple steps, high yield of each step and simple reaction; the reaction conditions of each step are mild, and the method has the advantages of low cost, high yield and easily available reaction conditions.

Boosting hydrogen evolution by using covalent frameworks of fluorinated cobalt porphyrins supported on carbon nanotubes

A cobalt(ii) tetrakis(2,3,5,6-tetrafluoro-4-ethynylphenyl)porphyrin (FCoP-H) was designed and synthesized. With carbon-nanotube-templated polymerization, covalent porphyrin frameworks using FCoP-H can be synthesized via the Hay-coupling. The resulting FCo

π-π Interaction assisted hydrodefluorination of perfluoroarenes by gold hydride: A case of synergistic effect on C-F bond activation

Synergistic effect is prevalent in natural metalloenzymes in activating small molecules, and the success has inspired the development of artificial catalysts capable of unprecedented organic transformations. In this work, we found that the attractive π-π interaction between organic additives (as electron-donors) and the perfluorinated arenes (as electron acceptors) is effective in gold hydride catalyzed activation of C-F bonds, specifically hydrodefluorination (HDF) of perfluoroarenes catalyzed by the Sadighi's gold hydrides [(NHC)AuH] (NHC = N-heterocyclic carbene). Although a weak interaction between [(NHC)AuH] and perfluoroarenes was observed from 1H NMR and UV-vis spectroscopies, low reactivity of [(NHC)AuH] toward HDF was found. In contrast, in the presence of p-N,N-dimethylaminopyridine (DMAP), the HDF of perfluoroarenes with silanes can be efficiently catalyzed by [(NHC)AuH], resulting in mainly the para-hydrodefluorinated products with up to 90% yield and 9 turnovers. The yield of the reaction increases with the more electron-withdrawing groups and degree of fluorination on the arenes, and the HDF reaction also tolerates different function groups (such as formyl, alkynyl, ketone, ester, and carboxylate groups), without reduction or hydrogenation of these function groups. To reveal the role of DMAP in the reactions, the possible π-π interaction between DMAP and perfluoroarenes was suggested by UV-vis spectral titrations, 1H NMR spectroscopic studies, and DFT calculations. Moreover, 1H and 19F-NMR studies show that this π-π interaction promotes hydrogen transfer from [(NHC)AuH] to pyridyl N atom, resulting in C-F bond cleavage. The interpretation of π-π interaction assisted C-F activation is supported by the reduced activation barriers in the presence of DMAP (31.6 kcal/mol) than that in the absence of DMAP (40.8 kcal/mol) for this reaction. An analysis of the charge distribution and transition state geometries indicate that this HDF process is controlled by the π-π interaction between DMAP and perfluoroarenes, accompanied with the changes of partial atomic charges.

Preparation of donor-acceptor substituted fluorostilbenes and crystal chemistry of fluorinated (E)-4-(4-halogeno-styryl)-benzonitriles

The syntheses and crystal structures of a series of fluoro-substituted halogeno (Cl, Br, I)-cyano-stilbenes containing donor and acceptor groups (D-π-A) are reported. These molecules show a tendency to form antiparallel chain-like structures and herringbone packing, crystallising predominantly in a centric space group. However, second harmonic generation measurements bear evidence for orientational disorder leading to partial polar order below the ordinary X-ray structure determination limit. Some co-crystals are isostructural with their components. The non-fluoro as well as the halogeno-fluoro substituted components of co-crystals seem to impose their crystal structure on the complementary fluoro- or cyano-fluoro substituted components. Co-crystallization enhanced the deviation from centrosymmetry.

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).

PROCESS FOR PRODUCING TETRAFLUORO BENZENEMETHANOLS

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.

Process for production of benzonitrile and benzyl alcohol

PCT No. PCT/JP97/03037 Sec. 371 Date Apr. 27, 1998 Sec. 102(e) Date Apr. 27, 1998 PCT Filed Aug. 29, 1997 PCT Pub. No. WO98/08795 PCT Pub. Date Mar. 5, 1998A process for producing a fluorinated benzonitrile comprising hydrogenolyzing a fluorinated dicyanobenzene substituted with 1 to 4 fluorine atoms and having the remainder which may be substituted with a chlorine atom in the presence of a catalyst to cause hydrodecyanation of only the cyano group of one side and a process for producing a fluorinated benzyl alcohol comprising reducing the fluorinated benzonitrile and hydrolyzing the fluorinated benzonitrile and reducing the resultant corresponding fluorinated benzoic acid to convert the cyano group to a hydroxymethyl group.