321-28-8

Usage

Chemical Properties

clear colorless liquid

Synthesis Reference(s)

Chemistry Letters, 23, p. 1011, 1994Tetrahedron, 52, p. 23, 1996 DOI: 10.1016/0040-4020(95)00867-8

Upstream product

• 367-12-4 2-fluorophenol 
• 492-95-5 2-methoxyphenyldiazonium tetrafluoroborate 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 13513-82-1 1-(2-methoxyphenyl)ethanol 
• 22788-49-4 2-methoxyphenyl(phenyl)methanol 
• 612-16-8 (2-methoxyphenyl)methanol 
• 64465-53-8 4-fluoro-3-methoxyaniline 
• 10365-98-7 3-methoxyphenylboronic acid 
• 5720-07-0 4-methoxyphenylboronic acid 
• 90-04-0 2-methoxy-phenylamine 
• 64-19-7 acetic acid 
• 100-66-3 methoxybenzene 
• 78948-09-1 acetyl hypofluorite 
• 74-88-4 methyl iodide 

Downstream Products

• 347-63-7 γ-(3-fluoro-4-methoxy)-γ-oxobenzenebutanoic acid 
• 351-52-0 3-fluoro-4-methoxybenzyl chloride 
• 331-61-3 3-fluoro-4-methoxybenzyl bromide 
• 92-18-2 N,N-diethyl-3-methoxyaniline 
• 367-12-4 2-fluorophenol 
• 344-78-5 6-fluoro-2,4-dinitroanisole 
• 455-93-6 2-fluoro-1-methoxy-4-nitrobenzene 
• 2265-90-9 2-hydroxy-1,5-dinitro-3-fluorobenzene 
• 2357-52-0 3-fluoro-4-methoxyphenyl bromide 
• 586-22-1 1-(3-fluoro-4-methoxyphenyl)propan-1-one 
• 390-67-0 1,1-bis-(3-fluoro-4-methoxy-phenyl)-propene 
• 455-91-4 1-(3-fluoro-4-methoxyphenyl)ethanone 
• 586-20-9 1-(3-fluoro-4-methoxy-phenyl)-pentan-1-one 
• 2113-56-6 3-methoxybiphenyl 

Relevant academic research and scientific papers

Reaction of Acetyl Hypofluorite with Aromatic Mercury Compounds: a New Selective Fluorination Method

Aromatic fluorine compounds are prepared in acetic acid from the corresponding mercury compounds and acetyl hypofluorite.

The regioselectivity in the fluorination of dibenzofuran, diphenylether and biphenyl with N-F type of reagents

Dibenzofuran, diphenylether and biphenyl were used as target molecules in an investigation of the effect of N-F type of reagent structure and reaction conditions on the fluorination process. The yields of fluorinated products formed and the regioselectivity depend on the reagent used, and in the reactions with dibenzofuran three products were formed. The ratios of 2-fluorodibenzofuran (4) and 3-fluorodibenzofuran (5) formed were: 1.3 for 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (NFTh, 1b), 1.4 for 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (F-TEDA, 1a), and 1.8 for N-fluoro-2,6-dichloropyridinium tetrafluoroborate (FPD-B, 1c). Ortho regioselectivity predominated for all reagents in the fluorination of biphenyl (ortho: para ratio varied from 4.8 to 1.2), while para attack prevailed for diphenylether (ortho: para = 0.9-0.7); however substitution of a phenyl ring by a methyl group enhanced the amount of 2-fluoroanisole. Second order rate constants for the fluorination of aromatic molecules with F-TEDA in acetonitrile at 65°C were established: anisole 4.8 x 10-3 Lmol-1s-1, dibenzofuran 2.5 x 10-4 Lmol-1s-1 an biphenyl 1.0 x 10-4 Lmol-1s-1.

N,N′-Difluoro-1,4-diazoniabicyclo[2.2.2]octane Salts, Highly Reactive and Easy-to-Handle Electrophilic Fluorinating Agents

A series of N,N′-difluoro-1,4-diazoniabicyclo[2.2.2]octane salts were synthesized in a pure form by the fluorination of 1,4-diazabicyclo[2.2.2]octane with F2 diluted with N2 in the presence of a Bronsted acid in fluoro alcohol or acetonitrile or by fluorination followed by a treatment with a different Bronsted or Lewis acid. Their complete structural assignment was made based on spectral and elemental analyses of the isolated crystals. A great through-bond interaction between the two N-F's of the salt was observed on 19FNMR. An assessment was made of the usefulness of N,N′-difluoro-1,4-diazoniabicyclo[2.2.2]octane bis(triflate), bis(HSO2), bis(BF4), and bis(SbF6) salts for electrophilic fluorination; the bis-(BF4) salt was demonstrated to be widely applicable as a highly reactive and easy-to-handle fluorinating agent. Thus, the bis(BF4) salt readily fluorinated activated aromatics, active methylene compounds or their salts, substituted styrenes, and vinyl acetates under mild conditions. It was shown that one N-F of the salt was effective for fluorination and that the other N-F played a role to activate fluorination through the bonds. Thus, the reaction mechanism was discussed, and fluorination followed by an immediate intramolecular one-electron transfer was suggested.

Radical Carbofluorination of Alkenes with Arylhydrazines and Selectfluor: Additives, Mechanistic Pathways, and Polar Effects

Radical carbofluorination reactions starting from arylhydrazines and nonactivated alkenes, in which the C?F bond is formed through the use of Selectfluor, can be improved through the addition of anisole. Because direct trapping products could be detected only in trace amounts, anisole does primarily act as a reversible scavenger for the highly reactive ammonium radical dication released from Selectfluor in the C?F bond-forming step. As shown for three diverse substitution patterns, the main role of anisole is to prevent, or at least reduce, the undesired addition of the ammonium radical dication to the alkene, which in turn leads to an unfavorable consumption of the arylhydrazine-derived precursors required for carbofluorination. Moreover, besides the remarkable polar effects in radical trapping, this study shows that the Selectfluor-derived nitrogen-centered radical dication may add directly to alkenes, which has not been described so far.

Electrophilic fluorination of aromatics with selectfluor and trifluoromethanesulfonic acid 1

1-(chloromethyl)-4-fluoro-1,4-diazabicyclo[2.2.2]octane bis (tetrafluoroborate) [Selectfluor F-TEDA-BF4 (TEDA = triethylenediamine)] in the presence of trifluoromethanesulfonic acid has been found to be a very effective reagent system for the direct electrophilic fluorination of a wide variety of aromatic compounds under mild reaction conditions to the corresponding fluoroaromatics in good to excellent yields.

DIRECT FLUORINATION OF PHENOL AND CRESOLS

A study has been made of the reaction of phenol with elemental fluorine using a variety of solvents and reaction temperatures.Yields of o- and p-fluorophenol were obtained as high as 85percent.The isomer ratio changed drastically between phenol conversions of 10percent and 56percent.The o-isomer changed to unidentified polymeric substances at higher conversion, but it might also be assumed that interconversion of some isomers is occuring.The three cresols have also been succesfully fluorinated with elemental fluorine. p-Cresol gave some expected 2-fluoroderivative but also formed a fluorocyclohexadienyl ketone.

Facile Preparation of Aromatic Fluorides by the Fluoro-Dediazoniation of Aromatic Diazonium Tetrafluoroborates Using HF-Pyridine Solution

The fluoro-dediazoniation of ArN2BF4 using HF-pyridine solution has been successfully carried out either thermaly or photochemically to afford the corresponding ArF in good yields.Particularly, the photochemically induced reaction in HF-pyridine was a useful tool for the preparation of ArF having polar substituents such as halogens, OH, OMe, CF3, etc.

Photochemical (Hetero-)Arylation of Aryl Sulfonium Salts

The construction of (hetero)biaryls, which are ubiquitous scaffolds among medical substances, functional materials, and agrochemicals, constitutes a key application of cross-coupling methods. However, these usually require multiple synthetic steps. Herein, we report a simple photoinduced and catalyst-free C-H/C-H (hetero)arylation cross-coupling through aryl thianthrenium salts, which are formed site-selectively by direct C-H functionalization. The key to this approach is the UV-light, which can disrupt the C-S bond to form thianthrene radical cations and aryl radicals.

Transition metal free, late-stage, regiospecific, aromatic fluorination on a preparative scale using a KF/crypt-222 complex

We herein report the development of a convenient, regioselective, aromatic fluorination method of hypervalent iodonium ylides for synthesising fluoro-arenes on a preparative scale. This transition metal free, nucleophilic methodology provides good yields for sterically hindered substrates, irrespective of activation. The methodology simplifies reference synthesis for PET imaging.

List fluoro Radicamine compounds and their use and preparation method

The invention discloses a mono-fluorinated Radicamine compound which has a structure as shown in a formula (1), and further provides a preparation method for the mono-fluorinated Radicamine compound with the structure as shown in the formula (1) and an application of the mono-fluorinated Radicamine compound or the mono-fluorinated Radicamine compound prepared with the method to preparation of drugs for preventing and/or treating diabetes, drugs for preventing and/or treating Gaucher's diseases, drugs for preventing and/or treating tumors or antiviral drugs. The mono-fluorinated Radicamine compound provided by the invention is good in glycosidase inhibition activity.