384-98-5

Usage

Uses

Used in Chemical Synthesis:
2,4,6-TRIMETHYLBENZENESULFONYL FLUORIDE is used as a connector in chemical synthesis for the assembly of -SO2linked small molecules with proteins or nucleic acids. Its sulfonyl fluoride motif enables the formation of stable and functional linkages, which can be useful in various chemical reactions and the development of new compounds.
Used in Click Chemistry:
2,4,6-TRIMETHYLBENZENESULFONYL FLUORIDE is used as a component in click chemistry approaches through sulfates. This method provides an alternative to using amides and phosphate groups as linkers, offering new possibilities for the creation of complex molecular structures and the development of innovative materials and drugs.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,4,6-TRIMETHYLBENZENESULFONYL FLUORIDE can be used as a building block for the development of new drugs. Its ability to form -SO2linked small molecules with proteins or nucleic acids can contribute to the design of novel therapeutic agents with improved efficacy and selectivity.
Used in Bioconjugation:
2,4,6-TRIMETHYLBENZENESULFONYL FLUORIDE is used as a bioconjugation agent for the attachment of small molecules to proteins or nucleic acids. This can be useful in the development of targeted drug delivery systems, biosensors, and other bioanalytical tools.
Overall, 2,4,6-TRIMETHYLBENZENESULFONYL FLUORIDE is a versatile compound with potential applications in various fields, including chemical synthesis, click chemistry, pharmaceuticals, and bioconjugation. Its unique sulfonyl fluoride motif allows for the formation of stable and functional linkages, making it a valuable component in the development of new materials and therapeutic agents.

Upstream product

• 108-67-8 1,3,5-trimethyl-benzene 
• 201230-82-2 carbon monoxide 
• 7789-21-1 fluorosulphonic acid 
• 16182-15-3 2,4,6-trimethylbenzenesulfonohydrazide 
• 6148-75-0 2,4,6-trimethylbenzenesulfonate sodium salt 
• 88-05-1 2,4,6-trimethylaniline 
• 24006-09-5 mesitylhydrazine hydrochloride 
• 773-64-8 2-mesitylenesulphonyl chloride 

Downstream Products

• 70265-12-2 2,4,6,2',4',6'-Hexamethyl-biphenyl-3,3'-disulfonyl difluoride 
• 22363-78-6 5,7-Dimethyl-3H-benzo[c][1,2]oxathiole 1,1-dioxide 
• 96913-13-2 3-(5,7-Dimethyl-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[c][1,2]oxathiol-6-yl)-2,4,6-trimethyl-benzenesulfonyl fluoride 
• 87589-14-8 3-(2-Fluorosulfonyl-3,5-dimethyl-benzyl)-2,4,6-trimethyl-benzenesulfonyl fluoride 
• 1254832-43-3 2-(fluoro(phenylsulfonyl)methylsulfonyl)-1,3,5-trimethylbenzene 
• 305849-15-4 N-(4-methoxybenzyl)-2,4,6-trimethylbenzenesulfonamide 
• 321531-69-5 2,4,6-tri-methyl-N-(pyridine-2-ylmethyl)benzenesulfonamide 
• 161452-12-6 N-(tert-butyl)-2,4,6-trimethylbenzenesulfonamide 
• 24906-63-6 2,4,6-trimethylbenzene-1-sulfonyl azide 
• 68985-08-0 2,4,6-trimethyl-1,3-benzenedisulfonyl dichloride 
• 392-49-4 3-nitro-2,4,6-trimethylbenzenesulfonyl fluoride 

Relevant academic research and scientific papers

A Broad-Spectrum Catalytic Amidation of Sulfonyl Fluorides and Fluorosulfates**

A broad-spectrum, catalytic method has been developed for the synthesis of sulfonamides and sulfamates. With the activation by the combination of a catalytic amount of 1-hydroxybenzotriazole (HOBt) and silicon additives, amidations of sulfonyl fluorides and fluorosulfates proceeded smoothly and excellent yields were generally obtained (87–99 %). Noticeably, this protocol is particularly efficient for sterically hindered substrates. Catalyst loading is generally low and only 0.02 mol % of catalyst is required for the multidecagram-scale synthesis of an amantadine derivative. In addition, the potential of this method in medicinal chemistry has been demonstrated by the synthesis of the marketed drug Fedratinib via a key intermediate sulfonyl fluoride 13. Since a large number of amines are commercially available, this route provides a facile entry to access Fedratinib analogues for biological screening.

Copper-catalyzed three-component reaction of arylhydrazine hydrochloride, DABSO, and NFSI for the synthesis of arenesulfonyl fluorides

This paper reports a convenient copper-catalyzed three-component conversion of arylhydrazine hydrochlorides to arenesulfonyl fluorides in good yields under mild conditions, using 1,4-diazabicyclo [2.2.2]octane bis(sulfur dioxide) (DABSO) as a sulfonyl source andN-fluorobenzenesulfonimide (NFSI) as a fluorine source based on a radical sulfur dioxide insertion and fluorination strategy. Notably, arylhydrazine hydrochloride is used as a safe precursor of aryl radicals.

Method for preparing aryl sulfonyl fluoride by using aryl hydrazine hydrochloride as raw material

The invention relates to a method for preparing aryl sulfonyl fluoride by using aryl hydrazine hydrochloride as a raw material. According to the method, aryl sulfonyl fluoride is synthesized by taking the aryl hydrazine hydrochloride as a raw material and adding a sulfur dioxide source and a fluorination reagent under the conditions of copper salt catalysis and alkali promotion through a strategy of insertion and fluorination of free radical sulfur dioxide. Compared with the prior art, the aryl sulfonyl fluoride is synthesized under the oxidation condition, and the influence of air on the reaction is not obvious in an experiment; and the reaction synthesis method is simple, good in selectivity, excellent in yield, mild in reaction condition, short in reaction time and universal to various aryl hydrazine hydrochloride substrates, and the method provides a new thought for synthesis of aryl sulfonyl fluoride.

Metal-Free Visible-Light Synthesis of Arylsulfonyl Fluorides: Scope and Mechanism

The first metal-free procedure for the synthesis of arylsulfonyl fluorides is reported. Under organo-photoredox conditions, aryl diazonium salts react with a readily available SO2 source (DABSO) to afford the desired product through simple nucleophilic fluorination. The reaction tolerates the presence of both electron-rich and -poor aryls and demonstrated a broad functional group tolerance. To shed the light on the reaction mechanism, several experimental techniques were combined, including fluorescence, NMR, and EPR spectroscopy as well as DFT calculations.

Facile one-pot synthesis of sulfonyl fluorides from sulfonates or sulfonic acids

A facile cascade process for directly transforming the abundant and inexpensive sulfonates (or sulfonic acids) to the highly valuable sulfonyl fluorides was developed. This new protocol features mild reaction conditions using readily available and easy-to-operate reagents. A diverse set of sulfonyl fluorides was prepared facilitating the enrichment of the sulfonyl fluoride library.

Catalyst-free radical fluorination of sulfonyl hydrazides in water

The first catalyst-free fluorination of sulfonyl hydrazides for the synthesis of sulfonyl fluorides has been developed via a free-radical pathway. This protocol presents a broad substrate scope and does not require any metal catalyst and additive. All these transformations proceed smoothly in water under mild conditions, which enables a straightforward, practical and environmentally benign fluorination for S-F bond formation.

Ascertaining the suitability of aryl sulfonyl fluorides for [18F]radiochemistry applications: A systematic investigation using microfluidics

Optimization of [18F]radiolabeling conditions and subsequent stability analysis in mobile phase, PBS buffer, and rat serum of 12 aryl sulfonyl chloride precursors with various substituents (electron-withdrawing groups, electron-donating groups, increased steric bulk, heterocyclic) were performed using an Advion NanoTek Microfluidic Synthesis System. A comparison of radiochemical yields and reaction times for a microfluidics device versus a conventional reaction vessel is reported. [18F]Radiolabeling of sulfonyl chlorides in the presence of competing nucleophiles, H-bond donors, and water was also assessed and demonstrated the versatility and potential utility of [18F]sulfonyl fluorides as synthons for indirect radiolabeling. Published 2013 by the American Chemical Society.

Dual Reactivity of the Formyl Cation as an Electrophile and a Broensted Acid in Superacids

The nature of the formyl cation in the Gattermann-Koch formylation was studied by comparing the formylation with the acetylation and sulfonation in CF3SO3H-SbF5 and FSO3H-SbF5, respectively.The results of the kinetic studies in CF3SO3H-SbF5 showed that the formyl cation has dual reactivity as an electrophile and as a Broensted acid.Upon comparing the formylation with the sulfonation in FSO3H-SbF5, it was found that the protonated aromatic compounds also act as Broensted acids to produce formyl cations.Therefore, the formylation has a priority over other typical electrophilic substitutions under conditions where most of aromatic compounds are protonated because the formyl cation is reproduced close to the aromatic compounds by the protonation of CO with not only superacids but also protonated aromatic compounds.

OXIDATION OF METHYL-SUBSTITUTED BENZENESULFONYL FLUORIDES IN THE PbO2-HSO3F SYSTEM

The transformations of the sulfonyl fluorides of methyl-substituted benzenes in the PbO2-HSO3F system were studied.They take place through a stage involving the one-electron oxidation of the substrate to aromatic radical-cations.One of the transformation paths of the latter is realized through the elimination of a proton from the methyl groups involved to the greatest degree in the delocalization of the unpaired electron.This leads to the formation of diarylmethanes and the fluorosulfonates of substituted benzyl alcohols, which give substituted tolylsultones and benzyl alcohols during hydrolysis of the acid solution and methyl ethers of benzyl alcohols during methanolysis.The other path, which arises during localization of the unpaired electron in the unsubstituted positions of the benzene ring, leads to biaryls.