1559-88-2

Usage

Uses

Used in Chemical Synthesis:
1-Bromo-2,3,5,6-tetrafluorobenzene is used as a key intermediate for the production of 1,2,4,5-tetrafluoro-3-hept-1-ynyl-benzene, a compound with potential applications in various chemical processes.
Used in Pharmaceutical Industry:
1-Bromo-2,3,5,6-tetrafluorobenzene is used as a pharmaceutical intermediate for the synthesis of various drugs and medicinal compounds. Its unique chemical structure allows for the development of new pharmaceuticals with improved properties and therapeutic effects.
Used in Fluorine Chemistry:
Due to its tetrafluorinated structure, 1-Bromo-2,3,5,6-tetrafluorobenzene can be utilized in fluorine chemistry for the preparation of fluorinated derivatives with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C6H3ClFI/c7-5-3-4(9)1-2-6(5)8/h1-3H

Upstream product

• 327-54-8 1,2,4,5-Tetrafluorobenzene 
• 344-03-6 1,4-dibromotetrafluorobenzene 
• 769-40-4 2,3,5,6-tetrafluorothiophenol 
• 2062-98-8 perfluoro(2-propoxypropionyl) fluoride 
• 31103-33-0 4-bromotetrafluorophenylmagnesium bromide 
• 139-02-6 sodium phenoxide 
• 652-18-6 2,3,5,6-tetrafluorobenzoic acid 
• 344-04-7 bromopentafluorobenzene 
• 2797-79-7 (4-bromo-2,3,5,6-tetrafluorophenyl)hydrazine 

Downstream Products

• 17823-37-9 1-bromo-2,3,5,6-tetrafluoro-4-nitrobenzene 
• 60903-81-3 1-Bromo-4H-hexafluoro-1,4-cyclohexadiene 
• 1835-58-1 4-bromotetrafluorophenyl(pentafluorophenyl)sulfane 
• 52331-31-4 bis(4-bromotetrafluorophenyl)sulfane 
• 23653-74-9 trimethyl(2,3,5,6-tetrafluorophenyl)tin 
• 148892-95-9 tris(2,3,5,6-tetrafluorophenyl)borane triethylphosphine oxide 
• 196882-77-6 (PEt₃)2NiF(2,3,5,6-F₄C₆H) 
• 1219809-82-1 (E)-1-bromo-2,3,5,6-tetrafluoro-4-styrylbenzene 
• 1219809-81-0 (E)-tert-butyl 3-(4-bromo-2,3,5,6-tetrafluorophenyl)acrylate 
• 1219809-88-7 (E)-di-tert-butyl 3,3'-(perfluoro-1,4-phenyl)diacrylate 
• 1094249-93-0 (Et₂O)B(p-C₆F₄H)3 
• 1244039-25-5 3-(4-bromo-2,3,5,6-tetrafluorophenyl)-1-methyl-1H-indole 
• 1244039-24-4 methyl 5-(4-bromo-2,3,5,6-tetrafluorophenyl)thiophene-2-carboxylate 
• 834-89-9 2,3,5,6-tetrafluorobiphenyl 

Relevant academic research and scientific papers

Transition-metal-free decarboxylative bromination of aromatic carboxylic acids

Methods for the conversion of aliphatic acids to alkyl halides have progressed significantly over the past century, however, the analogous decarboxylative bromination of aromatic acids has remained a longstanding challenge. The development of efficient methods for the synthesis of aryl bromides is of great importance as they are versatile reagents in synthesis and are present in many functional molecules. Herein we report a transition metal-free decarboxylative bromination of aromatic acids. The reaction is applicable to many electron-rich aromatic and heteroaromatic acids which have previously proved poor substrates for Hunsdiecker-type reactions. In addition, our preliminary mechanistic study suggests that radical intermediates are not involved in this reaction, which is in contrast to classical Hunsdiecker-type reactivity. Overall, the process demonstrates a useful method for producing valuable reagents from inexpensive and abundant starting materials.

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

Reactions of dibromotetrafluorobenzene derivatives with sodium phenoxide salts. Competing hydrodebromination and SNAr processes

1,2- and 1,3-dibromotetrafluorobenzene react with sodium phenoxide derivatives at sites para to ring bromine because these positions are activated by fluorine atoms ortho and meta to the site of nucleophilic substitution. Fluorine para to the site of nucl

Fluorophenylborates and their use as activators in catalyst systems for olefin polymerization

A fluorophenylborate useful as an activator for an olefin polymerization catalyst is represented by the formula: [in-line-formulae]Ct+[B—(ArfRn)4]?[/in-line-formulae]where Ct+ is a cation capable of extracting an alkyl group from, or breaking a carbon-metal bond of, an organo metallic compound; Arf is a fluorophenyl group; n is 1 or 2; and each R is independently selected from a fluorophenyl group and a fluoronaphthyl group, provided that when n=1, each R group is connected at the 3-position relative the connection between the associated Arf group and the boron atom and, when n=2; the R groups are connected at the 3-position and the 5-position respectively relative the connection between the associated Arf group and the boron atom.

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.

Preparation process of fluorine substituted aromatic compound

A preparation process of a fluorine substituted aromatic compound comprising reacting an alkali metal or alkali earth metal salt of an aromatic compound having a hydroxy group with an organic fluorinating agent is disclosed. As a representative fluorinating agent, a bis-dialkylamino-difluoromethane compound, for example, 2,2′-difluoro-1,3-dimethylimidazolidine, is exemplified. According to the process, an industrially useful fluorinated aromatic compound, for example, a fluorobenzene, a fluorine substituted benzophenone, a fluorine substituted diarylsulfone can be prepared with ease in economy without specific equipment.

Reaction of polyfluoroaromatic compounds with electrophilic agents in the presence of tris(dialkylamino)phosphines: 7. * Replacement of a halogen by hydrogen in halogenopolyfluoroaromatic compounds

A method was developed for the replacement of chlorine, bromine, and iodine in halopolyfluoroaromatic compounds by hydrogen under the action of P(NEt2)3 and a proton donor.