21622-19-5

Usage

Uses

Used in Chemical Synthesis:
1,2,3,4-Tetrafluoro-5-methylbenzene is utilized as an intermediate in the synthesis of other chemical compounds, playing a crucial role in the production of various industrial products.
Used in Pharmaceutical Production:
1,2,3,4-Tetrafluoro-5-methylbenzene is employed in the pharmaceutical industry, where it serves as a key component in the development of new drugs, contributing to the advancement of medical treatments.
Used in Agrochemical Production:
1,2,3,4-Tetrafluoro-5-methylbenzene is also used in the agrochemical sector, where it is involved in the creation of products that support agricultural practices, such as pesticides and fertilizers.

InChI:InChI=1/C7H4F4/c1-3-2-4(8)6(10)7(11)5(3)9/h2H,1H3

Upstream product

• 5121-89-1 1-iodo 2,3,4,5-tetrafluoro benzene 
• 5158-46-3 methylzinc chloride 
• 551-62-2 1,2,3,4-tetrafluorobenzene 
• 771-56-2 2,3,4,5,6-pentafluorotoluene 
• 917-54-4 methyllithium 
• 377-70-8 perfluoro-1,3-cyclohexadiene 
• 21621-81-8 2-Methyl-1,4,5,6,7,7,8,8-octafluor-bicyclo<2.2.2>octadien-(2,5) 

Relevant academic research and scientific papers

Understanding the Use of Phosphine-(EWO) Ligands in Negishi Cross-Coupling: Experimental and Density Functional Theory Mechanistic Study

The easily prepared hemilabile ligand 1-(PPh2),2-(trans-CH═CHCOPh)-C6F4(PhPEWO-F) and other PEWO ligands are well-known promoters of C-C reductive eliminations and very effective in Negishi couplings. As an example, the efficient Negishi coupling of (C6F5)-I and Zn(C6F5)2is reported. The thorough experimental study of the steps involved in the catalytic cycle uncovers the potential weakness of this ligand that could frustrate at some points the desired cycle and provide some simple precautions to keep the catalytic cycle working efficiently. Density functional theory (DFT) calculations complete the experimental study and provide insight into nonobservable transition states and intermediates, comparing the potential conflict between reductive elimination and olefin insertion. Our results showcase the importance the transmetalation step, facilitated by the strong trans effect of the electron-withdrawing ligand, and the choice of organozinc nucleophiles, critical to ensure fast group exchange and a positive outcome of the catalytic reactions.

Friedel–Crafts Type Methylation with Dimethylhalonium Salts

The dimethylchloronium salt [Me2Cl][Al(OTeF5)4] is used to methylate electron-deficient aromatic systems in Friedel–Crafts type reactions as shown by the synthesis of N-methylated cations, such as [MeNC5F5]+, [MeNC5F4I]+, and [MeN3C3F3]+. To gain a better understanding of such fundamental Friedel–Crafts reactions, the role of the dimethylchloronium cation has been evaluated by quantum-chemical calculations.

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.

Substitution of fluorine in M[C6F5BF3] with organolithium compounds: Distinctions between O- and N-nucleophiles

Borates M[C6F5BF3] (M = K, Li, Bu4N) react with organolithium compounds, RLi (R = Me, Bu, Ph), in 1,2-dimethoxyethane or diglyme to give M[4-RC6F4BF3] and M[2-RC6Fsub