21622-19-5

Basic information

• Product Name: 1,2,3,4-Tetrafluoro-5-methylbenzene
• Synonyms: 1,2,3,4-Tetrafluoro-5-methylbenzene
• CAS NO: 21622-19-5
• Molecular Formula: C₇H₄F₄
• Molecular Weight: 164.1
• Mol File: 21622-19-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 124.9°C at 760 mmHg
• Flash Point: 31.6°C
• Appearance: /
• Density: 1.339g/cm³
• Vapor Pressure: 15.1mmHg at 25°C
• Refractive Index: 1.42
• CAS DataBase Reference: 1,2,3,4-Tetrafluoro-5-methylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-Tetrafluoro-5-methylbenzene(21622-19-5)
• EPA Substance Registry System: 1,2,3,4-Tetrafluoro-5-methylbenzene(21622-19-5)

Safety Data

• Hazardous Substances Data: 21622-19-5(Hazardous Substances Data)

Usage

General Description

1,2,3,4-Tetrafluoro-5-methylbenzene, also known as 2,3,4,5-Tetrafluorotoluene, is a chemical compound with the molecular formula C7H5F4. It is a colorless liquid with a molecular weight of 162.11. This chemical is used as an intermediate for the synthesis of other chemical compounds and is also used in the production of pharmaceuticals and agrochemicals. It is considered to be stable under normal conditions, but it may react violently with strong oxidizing agents and strong bases. Its primary hazard is its potential to cause fires and explosions. Overall, 1,2,3,4-Tetrafluoro-5-methylbenzene has a variety of industrial applications but should be handled with care due to its potential hazards.

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

Upstream product

• 917-54-4 methyllithium 
• 5121-89-1 1-iodo 2,3,4,5-tetrafluoro benzene 
• 5158-46-3 methylzinc chloride 
• 551-62-2 1,2,3,4-tetrafluorobenzene 
• 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) 
• 771-56-2 2,3,4,5,6-pentafluorotoluene 

Relevant articles and documents

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.

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.