191793-47-2

Upstream product

• 621-23-8 1,2,3-trimethoxybenzene 
• 67-56-1 methanol 
• 392-69-8 1-fluoro-2,4,6-trimethylbenzene 

Downstream Products

• 649-16-1 4,4-Difluoro-3,5-dimethoxycyclohexa-2,5-dien-1-one 

Relevant academic research and scientific papers

N-Halogeno compounds. Part 20. Vicarious electrophilic fluorodemethylation of 1,3,5-trimethoxybenzene and 2,4,6-trimethoxytoluene with 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor reagent F-TEDA-BF4

Treatment of 1,3,5-trimethoxybenzene with one molar equivalence of 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (F-TEDA-BF4) under mild conditions (-40 to +20°C) in acetonitrile gave mainly 2-fluoro-1,3,5-trim

Fluorination of supramolecular liquid crystals-tuning tool and analytical probe

A study on the impact of fluorination on the properties of photo-responsive hydrogen-bonded liquid crystals is reported. The chosen modular approach allows for efficient screening of a variety of hydrogen-bonded assemblies. Tremendous effects on the mesophase stabilization and morphology are described. In addition, the fluorine substituents are used as analytical probes for 19F solid-state NMR studies, providing insight into the molecular alignment of the assemblies.

Shielding Effect of Micelle for Highly Effective and Selective Monofluorination of Indoles in Water

Highly selective direct monofluorination of indoles and arenes was developed through an approach that allows site-specific solubility of substrate and fluorine source in the micelle. This approach was highly selective for a broad range of substrates with excellent functional group tolerance. Differences in binding constant and solubility of indoles and arenes in the micelle allowed the fine-tuning of selectivity. Control experiments suggested a radical pathway and provided insight into the role of micelles of the environmentally benign amphiphile PS-750-M. Dynamic light scattering experiments strongly indicated the site-specific solubility of the substrate and fluorine source. The methodology was successfully adapted to gram scale, and the E-factor established from a recycle study indicated that the process is environmentally responsible and sustainable.

Single-step syntheses of no-carrier-added functionalized [ 18F]fluoroarenes as labeling synthons from diaryliodonium salts

Radiotracers labelled with short-lived fluorine-18 (t1/2 = 109.7 min) are keenly sought for biomedical imaging with positron emission tomography (PET). The radiotracers are mostly required at high specific radioactivities, necessitating their radiosyntheses from cyclotron-produced no-carrier-added [18F]fluoride ion. PET radiotracers encompass wide structural diversity and molecular weight. Hence, diverse 18F-labeling methodology is needed to accomplish the required radiosyntheses in a simple and rapid manner. A useful strategy is to introduce nucleophilic [ 18F]fluoride ion first into a labeling synthon that may then be applied to label the target radiotracer. Here, we show that various functionalized [18F]fluoroarenes may be rapidly synthesized as labeling synthons through single-step reactions of appropriate diaryliodonium salts with [18F]fluoride ion. Decay-corrected radiochemical yields (RCYs) varied with position of functional group, choice of electron-rich aryl ring in the diaryliodonium salt, and choice of anion. Under best conditions, 18F-labeled fluorobenzaldehydes, fluorobenzyl halides, fluorobenzoic acid esters and fluorophenyl ketones were obtained selectively in 40-73%, 20-55%, 46-89% and 81-98% RCYs, respectively. This versatile straightforward methodology will enhance the scope for producing structurally complex, yet useful, PET radiotracers.

N-Halogeno compounds part 19: Electrophilic fluorinating agents of the multiple mono-N-fluoro class derived from nitrogen heterocycles

Bis(4-fluoro-1,4-diazoniabicyclo[2.2.2]oct-1-yl)-ethane and -propane tetratriflates (4, 5), and 1,1′-difluoro-4,4′-bipyridinium ditriflate (6) were prepared by solution-phase direct fluorination of bis(4-aza-1-azoniabicyclo[2.2.2]oct-1-yl)-ethane or -propane ditriflate (10, 11), and 4,4′-bipyridine respectively. The same technique was employed to convert the complex 4,4′-bipyridine · 2BF3 to the mono-NF derivative F3B-NC5H4-C5H4N+-F BF4- (7) and its monomethylated analogue (4-NC5H4)C5H4N+-CH3 TfO- to F-+ NC5H4-C5H4N+-CH3 (TfO- )2 (8). The results of site-specific electrophilic fluorination of some model substrates (1-morpholinocyclohexene, phenol, 2-naphthol, anisole, di-and tri-methoxybenzene) with 5, 7 and 8 are presented.

TRANSITION METAL ARENE COMPLEXES IN REACTIONS WITH NUCLEOPHILIC REAGENTS. XV. NUCLEOPHILIC REPLACEMENT OF THE FLUORINE ATOM BY THE METHOXY GROUP CATALYSED BY (η-BENZENE)(η-ETHYLTETRAMETHYLCYCLOPENTADIENYL)-RHODIUM(III) IN THE REACTION OF FLUOROARENES WITH METHANOL

The replacement of the fluorine atom by a methoxy group in the reaction of fluoroarenes with methanol is efficiently catalysed by 2+(PF6-)2, which permits the synthesis of alkyl aryl ethers under mild conditions without using alkali.Evidence was obtained indicating that the catalysis is a consequence of activation of the fluoroarenes upon their reversible ?-coordination with the 2+ fragmant.The yield of the products of the methanolysis of fluorobenzene and its derivatives and also of 1-fluoronaphthalene depends significantly on the structure of the aryl group and in creases in the series: 2-FC6H4F 2,4,6-Me3C6H2F 2-ClC6H4F 4-HOC6H4F 3,4-Me2C6H3F 1-C10H7F 2-, 3- and 4-MeC6H4F or MeOC6H4F C6H5F.The effect of the concentration of the methanol and the catalyst and of temperature on the reaction rate was studied.