1835-61-6

Usage

Uses

Used in Pharmaceutical Industry:
1-Chloro-2,3,5,6-tetrafluorobenzene is used as a key intermediate in the production of pharmaceuticals for its ability to be incorporated into the molecular structures of various drugs, enhancing their therapeutic properties and effectiveness.
Used in Agrochemical Industry:
Similarly, in the agrochemical sector, 1-chloro-2,3,5,6-tetrafluorobenzene serves as an intermediate, contributing to the development of compounds that address agricultural needs such as pest control and crop protection.
Used as a Solvent:
1-Chloro-2,3,5,6-tetrafluorobenzene is also utilized as a solvent in certain chemical processes due to its unique solvency properties, facilitating reactions in the synthesis of specific compounds.
Used as a Reagent in Organic Synthesis:
Furthermore, it functions as a reagent in organic synthesis, where its specific chemical characteristics are leveraged to drive reactions towards desired outcomes in the creation of complex organic molecules.
Safety and Environmental Considerations:
Given its potential hazards to human health and the environment, 1-chloro-2,3,5,6-tetrafluorobenzene necessitates careful handling and the implementation of proper protective measures during its use in various applications. Minimizing exposure and adhering to safety protocols are crucial to mitigate risks associated with 1-CHLORO-2,3,5,6-TETRAFLUOROBENZENE.

InChI:InChI=1/C6HClF4/c7-4-5(10)2(8)1-3(9)6(4)11/h1H

Upstream product

• 1198-62-5 1,4-dichloro-2,3,5,6-tetrafluorobenzene 
• 344-07-0 1-chloro-2,3,4,5,6-pentafluorobenzene 
• 769-40-4 2,3,5,6-tetrafluorothiophenol 
• 67-66-3 chloroform 
• 13634-93-0 4-chloro-2,3,5,6-tetrafluorobenzenethiol 
• 363-72-4 Pentafluorobenzene 
• 2716-07-6 4-chloro-2,3,5,6-tetrafluorophenylhydrazine 
• 344-03-6 1,4-dibromotetrafluorobenzene 

Downstream Products

• 56354-50-8 Bis(4-chloro-2,3,5,6-tetrafluorophenyl)sulfide 
• 776-09-0 2,3,5,6-tetrafluorobenzenesulfonyl chloride 
• 1073339-11-3 4,4,5,5-tetramethyl-2-(2,3,5,6-tetrafluorophenyl)-1,3,2-dioxaborolane 
• 1415155-96-2 C₁₁ClF₈NOSe 
• 1415155-93-9 C₁₁ClF₈NSe 
• 1415155-88-2 C₆Cl₂F₄Se 
• 142023-33-4 (C₆F₄Cl)2Se₂ 
• 1835-58-1 4-bromotetrafluorophenyl(pentafluorophenyl)sulfane 

Relevant academic research and scientific papers

Diazaphospholene-Catalyzed Hydrodefluorination of Polyfluoroarenes with Phenylsilane via Concerted Nucleophilic Aromatic Substitution

The metal-free catalytic C-F bond activation of polyfluoroarenes was achieved with diazaphospholene as the catalyst and phenylsilane as the terminal reductant. Density functional theory calculations suggested a concerted nucleophilic aromatic substitution mechanism.

Transition-Metal-Free Catalytic Hydrodefluorination of Polyfluoroarenes by Concerted Nucleophilic Aromatic Substitution with a Hydrosilicate

A transition-metal-free catalytic hydrodefluorination (HDF) reaction of polyfluoroarenes is described. The reaction involves direct hydride transfer from a hydrosilicate as the key intermediate, which is generated from a hydrosilane and a fluoride salt. The eliminated fluoride regenerates the hydrosilicate to complete the catalytic cycle. Dispersion-corrected DFT calculations indicated that the HDF reaction proceeds through a concerted nucleophilic aromatic substitution (CSNAr) process.

Synthesis of chloropolyfluoroarenes from polyfluoroarenethiols and PCl5

Replacement of the thiol group in polyfluoroarenethiols with chlorine was performed by treating with PCl5 as chlorinating agent. By heating in ampules at 200-220°C polyfluoro- and polyfluorochloroarenethiols with PCl5 mono- and dichloropolyfluoroarenes and also 1,2,4-trifluorotrichlorobenzene were synthesized. Dichloropolyfluoroarenes contain chlorine atoms in ortho- and para-positions.

Reactions of polyfluorobenzenethiols with polyhalomethanes and their derivatives in an alkaline medium

New process direction was found in the reaction of polyfluoroarenethiols with fluorodichloromethane, chloroform, and bromoform in an alkaline medium consisting in the replacement of the thiol group by a hydrogen atom. This process competes with the formation of expected products, dihalomethyl polyfluoro-aryl sulfides and tris(arylsulfanyl)methanes. In reaction of 2,3,5,6-tetrafluorobenzenethiol with dichloro-methane bis(2,3,5,6-tetrafluorophenylsulfanyl)methane was obtained. Reactions of polyfluoroarenethiols with pentafluorobenzyl chloride occur mainly with the substitution of the chlorine atom, with pentafluorobenzal chloride and with pentafluorobenzotrichloride a substitution of a fluorine atom in the para-position takes place.

Copper-catalyzed hydrodefluorination of fluoroarenes by copper hydride intermediates

Breaking bad: Efficient copper-catalyzed C-F bond activation has been achieved by replacing fluorine with hydrogen. A copper hydride is proposed as the active intermediate, which proceeds through a nucleophilic attack on the fluorocarbon, as determined by experimental and theoretical results (see structure; C gray, H white, Cu light red, F light blue; distances in ?).

Catalytic C-F bond activation of perfluoroarenes by tricoordinated gold(I) complexes

We report the first example of gold catalyzing C-F bond activation for perfluoroarenes in the presence of silanes. Tricoordinated gold(I) complexes supported by Xantphos-type ligands, such as Xantphos and tBuXantphos ligands, exhibit efficacy in the hydrodefluorination (HDF) of various types of perfluoroarenes. For [tBuXantphosAu(AuCl2)], the highest turnover number is up to 1000 in the HDF of pentafluoronitrobenzene with diphenylsilane. An examination of functional group tolerance shows the orthogonality of this gold(I) catalytic protocol to ketone, ester, carboxylate, alkynyl, alkenyl and amide groups, suggesting its potential application in chemoselective C-F activations. Mechanistic studies show that the equilibrium between tetracoordinated [L2Au]+ and [LAu]+ is important for the reactivity of gold catalysts, which is dependent on the sterically bulky group of Xantphos-type ligands. Furthermore, computational studies for the possible reaction pathways suggest that direct oxidative addition of C-F bonds by gold(I) cation might be the key step during these catalytic reactions. Copyright

Organofluorine sulfur-containing compounds: V. Joint pyrolysis with chlorine or bromine of polyfluoroarenethioles, polyfluorohetarenethioles, and their derivatives

Joint pyrolysis with chlorine and bromine of polyfluoroarenethiols, -hetarenethiols, and their derivatives at 300-650°C furnished polyfluorocompounds containing chlorine and bromine. 2005 Pleiades Publishing, Inc.

Method for producing tetrakis ( fluoroaryl) borate-magnesium compound

Fluoroaryl magnesium halide is reacted with a boron compound so that a molar ratio of the fluoroaryl magnesium halide to the boron compound is not less than 3.0 and not more than 3.7, so as to produce a tetrakis (fluoroaryl) borate·magnesium compound. With this method, there occurs no hydrogen fluoride which corrodes a producing apparatus and requires troublesome waste water treatment.

REACTION OF PERFLUOROARYL HALIDES WITH REDUCED SPECIES OF SULFUR DIOXIDE (HSO2(-), SO2(2-), S2O4(2-))

Rongalite (sodium hydroxymethanesulfinate), sodium dithionite, and aminoiminomethanesulfinic acid (AIMS) reduce perfluoroiodobenzene in N,N-dimethylformamide to pentafluorobenzene.In the presence of added D2O or CH3OD, deuteriopentafluorobenzene is formed. p-Dinitrobenzene does not inhibit the reduction, and addition of norbonene did not result in trapping of any radical intermediates.Reaction of pentafluoroiodobenzene with sodium benzenesulfinate gave 1,4-dibenzenesulfonyl-2,3,5,6-tetrafluorobenzene.A halophilic attack mechanism is suggested for the reduction reaction.Chloropentafluorobenzene did not react under the same conditions as the iodide; at elevated temperatures in the presence of sodium bicarbonate and Rongalite the fluorine para to the chlorine was reduced.Reduction of the chloride to pentafluorobenzene is minor.In the absence of bicarbonate, the chloride gave also a mixture of sulfides believed to be derived from decomposition of the Rongalite to hydrogen sulfide.Some reaction with dimethylamine from decomposition of DMF also is observed.