461-97-2

Usage

Uses

Used in Pharmaceutical Industry:
5-Fluoro-m-xylene is used as a key intermediate in the synthesis of iminodiaziridines, which are a class of nitrogen-containing heterocyclic compounds with potential applications in medicinal chemistry. These iminodiaziridines have been found to possess interesting biological activities, such as anticancer and antiviral properties, making them promising candidates for the development of new pharmaceutical agents.
Used in Polymer Industry:
In the polymer industry, 5-fluoro-m-xylene is utilized in the preparation of halogen-containing polyisophthalamides. These polymers are known for their excellent thermal stability, flame retardancy, and mechanical properties, which make them suitable for various high-performance applications, such as aerospace, automotive, and electrical insulation materials. The incorporation of fluorine atoms in the polymer backbone further enhances their performance characteristics, including chemical resistance and oxidative stability.

InChI:InChI=1/C8H9F/c1-6-3-7(2)5-8(9)4-6/h3-5H,1-2H3

Upstream product

• 452-64-2 3,4-dimethyl-fluorobenzene 
• 108-69-0 3,5-dimethylaminoaniline 
• 172975-69-8 3,5-dimethylphenyl boronic acid 
• 22445-41-6 3,5-dimethylphenyl iodide 
• 108-38-3 m-xylene 
• 325142-93-6 2-(3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1357166-41-6 (3,5-dimethylphenyl)(2,4,6-trimethylphenyl)iodonium tetrafluoroborate 

Downstream Products

• 315-12-8 2,6-dimethyl-4-fluoro-1-nitro-benzene 
• 315-13-9 1-fluoro-3,5-dimethyl-2-nitrobenzene 
• 1583-66-0 5-fluoroisophthalic acid 
• 19254-80-9 1,3-bis(bromomethyl)-5-fluorobenzene 
• 3995-39-9 N,N-diethyl-3,5-dimethylaniline 
• 255375-89-4 3,5-bis(dibromomethyl)fluorobenzene 
• 14659-58-6 2‐bromo‐5‐fluoro‐1,3‐dimethylbenzene 
• 14659-61-1 2,6-dimethyl-4-fluorobenzonitrile 
• 404337-41-3 diazobis(4-fluoro-2,6-dimethylphenyl)methane 
• 404337-40-2 bis(4-fluoro-2,6-dimethylphenyl)ketimine 
• 255375-90-7 5-fluorobenzene-1,3-dicarboxyaldehyde 
• 255375-91-8 5-fluoroisophthalaldehyde bis(propane-1,3-diyl dithioacetal) 
• 154742-96-8 (3-{[Bis-(2-pyridin-2-yl-ethyl)-amino]-methyl}-5-fluoro-benzyl)-bis-(2-pyridin-2-yl-ethyl)-amine 
• 75476-00-5 4-acetyl-4'-amino-2,6,3',5'-tetramethyldiphenyl ether 

Relevant academic research and scientific papers

Full continuous flow synthesis process of fluorine-containing aromatic hydrocarbon compounds

The invention provides a full continuous flow synthesis process of a fluorine-containing aromatic hydrocarbon compound, and belongs to the technical field of preparation of halogenated hydrocarbon carbocyclic organic compounds. Arylamine and hydrogen fluoride are pumped into a thermostat A and a thermostat B respectively and flow into a micro-channel reactor C for a salt forming reaction after constant temperature treatment, and a sulfuric acid solution of nitrosyl sulfuric acid is pumped into a thermostat D and flows into a micro-channel reactor E together with a salt forming product flowing out of the micro-channel reactor C for a diazotization reaction after constant temperature treatment. A product flows into a micro-channel reactor F to be subjected to a thermal decomposition reaction, is cooled by a cooler G and then enters a three-phase separator H to be continuously separated, nitrogen is discharged after being subjected to spraying deacidification, a fluorine-containing aromatic hydrocarbon crude product is subjected to continuous alkali washing, continuous drying and continuous rectification to obtain a fluorine-containing aromatic hydrocarbon finished product, and a hydrofluoric acid and sulfuric acid mixture is subjected to continuous distillation to obtain a product. The hydrogen fluoride and sulfuric acid are obtained. The full continuous flow synthesis process has the advantages of high reaction yield, excellent product quality, good production safety, less pollutant discharge and the like.

Preparation method of 3,5-dimethylfluorobenzene

The invention provides a preparation method of 3, 5-dimethylfluorobenzene, which comprises the following steps: adding 3,5-dimethylaniline into anhydrous hydrogen fluoride to generate hydrogen fluoride salt of 3,5-dimethylaniline; then adding sodium nitri

Synthetic method for 1,5-bis(chloromethyl)-3-fluorobenzene

The invention discloses a synthetic method for 1,5-bis(chloromethyl)-3-fluorobenzene, which belongs to the field of chemical synthesis. The synthetic method comprises the following steps: adding concentrated sulfuric acid and fuming nitric acid into 3,5-dimethylchlorobenzene and carrying out a reaction in an ice bath so as to obtain 3,5-dimethylnitrobenzene; then adding ethanol and palladium charcoal and introducing hydrogen so as to obtain 3,5-dimethylaniline; allowing 3,5-dimethylaniline and tetrafluoroboric acid to undergo an ice bath and adding a sodium nitrite solution drop by drop; carrying out filtering after completion of addition and drying obtained filter residue; and placing the filter residue in a flask for decomposition, adding water and petroleum ether and carrying out distillation so as to obtain 1,5-bis(chloromethyl)-3-fluorobenzene.

FLUORINATION OF ARYL COMPOUNDS

The invention provides compositions and methods of using the compositions in fluorinating aryl precursors containing a leaving group replaceable by a fluorine atom. The compositions include a metal ion source, a electrophilic fluorine source, a base, and a compound, which is an aryl precursor of the aryl fluoride, and which has a leaving group replaceable by the fluorine atom. Exemplary methods of the invention make use of such compositions and methods to prepare an aryl fluoride compound. In an exemplary embodiment, the electrophilic fluorine source is a source of 18F.

Cu-catalyzed fluorination of diaryliodonium salts with KF

A mild Cu-catalyzed nucleophilic fluorination of unsymmetrical diaryliodonium salts with KF is described. This protocol preferentially fluorinates the smaller aromatic ligand on iodine(III). The reaction exhibits a broad substrate scope and proceeds with high chemoselectivity and functional group tolerance. DFT calculations implicate a CuI/CuIII catalytic cycle.

Copper-mediated fluorination of arylboronate esters. Identification of a Copper(III) fluoride complex

A method for the direct conversion of arylboronate esters to aryl fluorides under mild conditions with readily available reagents is reported. Tandem reactions have also been developed for the fluorination of arenes and aryl bromides through arylboronate ester intermediates. Mechanistic studies suggest that this fluorination reaction occurs through facile oxidation of Cu(I) to Cu(III), followed by rate-limiting transmetalation of a bound arylboronate to Cu(III). Fast C-F reductive elimination is proposed to occur from an aryl-copper(III)-fluoride complex. Cu(III) intermediates have been generated independently and identified by NMR spectroscopy and ESI-MS.

Continuous flow reactor for Balz-Schiemann reaction: A new procedure for the preparation of aromatic fluorides

A facile and highly efficient procedure for the preparation of aromatic fluorides by Balz-Schiemann reaction via two continuous flow reactors has been set up. The continuous diazotization reactor was run at about 25 °C with residence times of 10-20 s, and the continuous fluorodediazoniation reactor was performed with a residence time of 1 min in high yields. The reaction times can be greatly reduced by increasing temperature and thereby taking advantage of superior mass and heat transfer of a continuous flow system.

Copper-mediated fluorination of aryl iodides

The synthesis of aryl fluorides has been studied intensively because of the importance of aryl fluorides in pharmaceuticals, agrochemicals, and materials. The stability, reactivity, and biological properties of aryl fluorides can be distinct from those of the corresponding arenes. Methods for the synthesis of aryl fluorides, however, are limited. We report the conversion of a diverse set of aryl iodides to the corresponding aryl fluorides. This reaction occurs with a cationic copper reagent and silver fluoride. Preliminary results suggest this reaction is enabled by a facile reductive elimination from a cationic arylcopper(III) fluoride.

FLUORINATION OF ORGANIC COMPOUNDS

Methods for fluorinating organic compounds are described herein.

Fluorination of boronic acids mediated by silver(I) Triflate

A regiospecific Ag-mediated fluorination reaction of aryl- and alkenylboronic acids and esters Is reported. The fluorination reaction uses commercially available reagents, does not require the addition of exogenous ligands, and can be performed on a multigram scale. This report discloses the first practical reaction sequence from arylboronic acid to aryl fluorides.