51417-64-2

Upstream product

• 93-04-9 2-Methoxynaphthalene 
• 135-19-3 β-naphthol 
• 140681-68-1 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(trifluoromethanesulfonate) 
• 91-20-3 naphthalene 
• 2283-08-1 2-hydroxy-1-naphthalenecarboxylic acid 
• 93-18-5 2-ethoxynaphthalene 

Downstream Products

• 51417-63-1 1-fluoronaphthalen-2-ol 

Relevant academic research and scientific papers

SelectfluorTMon a PolyHIPE Material as Regenerative and Reusable Polymer-Supported Electrophilic Fluorinating Agent

The first recyclable polymer-supported electrophilic fluorinating agent was prepared by reaction of molecular fluorine with the triethylenediamine motif that is grafted onto a poly(4-vinylbenzyl chloride-co-divinylbenzene) polyHIPE material. The resulting

Ionic liquid-assisted grinding: An electrophilic fluorination benchmark

We demonstrated the influence of liquid additives on the rate and selectivity of mechano-chemical fluorination of aromatic and 1,3-dicarbonyl compounds with F-TEDA-BF4. Substoichio-metric catalytic quantities of ionic liquids speed up the react

Decarboxylative Fluorination of Arylcarboxylic Acids Promoted by ortho-Hydroxy and Amino Groups

A novel decarboxylative fluorination process has been developed for the synthesis of ortho-hydroxy/amino arylfluorides from salicylic acid analogs, in which the ortho-hydroxy/amino group plays an important role in the transformation. In addition, various arylfluorides are obtained in good to excellent yields under mild conditions.

Solvent-Free Fluorination of Electron-Rich Aromatic Compounds with F-TEDA-BF4: Toward “Dry” Processes

An effective protocol for the solvent-free fluorination of electron-rich aromatic compounds with 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (F-TEDA-BF4) is described. The protocol allows the easy and efficie

Fluorination of aromatic compounds with N-fluorobenzenesulfonimide under solvent-free conditions

Reactions of N-fluorobenzenesulfonimide with methylbenzenes, phenols, and phenol ethers were studied under solvent-free conditions. The rate constant ratio for the reactions with mesitylene and durene indicates polar mechanism of the process. Solvent-free fluorination of aromatic compounds with N-fluorobenzenesulfonimide in some cases is more selective than reactions with other N-F reagents in a solvent.

Fluorination of activated aromatic systems with Selectfluor F-TEDA-BF4 in ionic liquids

Selectfluor was shown to be soluble in ionic liquid, thus allowing the 'green' electrophilic fluorination of activated aromatic systems compounds in high chemoselectivity and yields.

Electrophilic fluorination with N,N′-difluoro-2,2′-bipyridinium salt and elemental fluorine

NNpm-Difluoro-22pm-bipyridiniu m bis(tetrafluoroborate) (MEC-31) was shown to be a highly reactive electrophilic fluorinating agent with the highest effective fluorine content in its class. We have developed the perfect recycled fluorination system with MEC-31 for the lower-cost industrial fluorination and for an environment. MEC-31 can be completely recycled including the counter-anion. We found the fluorination of 2-naphthol in liquid CO2 with MEC-31 in the presence of catalytic amount of NaOTf proceeded quantitatively without the generation of by-product. In the fluorination of 1,3-dicarbonyl compounds with elemental fluorine, we found the introduction method of fluorine gas would be very important in order to make a reaction efficient. As fluorination goes on, the quantity of 1,3-dicarbonyl compounds of the starting material is reduced gradually, and therefore the quantity of fluorine must be reduced by the method to control the flow rate or the concentration of fluorine gas diluted with nitrogen, together the fluorination to proceed efficiently.

Synthesis, Properties, and Reactivity of N,N'-Difluorobipyridinium and Related Salts and Their Applications as Reactive and Easy-To-Handle Electrophilic Fluorinating Agents with High Effective Fluorine Content

N,N′-Difluoro-2,2′-, -2,4′-, -3,3′-, -4,4′-bipyridinium and substituted N,N′-difluoro-2,2′-bipyridinmm bis(triflates), bis(tetrafluoroborates), bis(hexafluorophosphates), and bis(hexafluoroantimonates) 1-9 were synthesized in high yields by the direct fluorination of a mixture of a bipyridyl and a Lewis acid, a Br?nsted acid, or the alkali metal salt of an acid. The higher homologues, trimer 10 and polymer 11, were also synthesized. Unsubstituted or electron-donating group-substituted N,N′- difluorobipyridinium salts are stable nonhygroscopic crystals, while the electron-withdrawing group- substituted N,N′-diflurobipyridinium salts 3, 5, and 6 are moisture-sensitive crystals. Hydrolysis of 1b in boiling water gave 3,3′-dihydroxy-2,2′-bipyridyl. The reactivity determination indicated that the fluorinating capability decreased in the order 2,2′- ? 2,4' > 3,3′- ≈ 4,4′-isomer ? N-fluoropyridinium salt and that the two N-F moieties in a molecule were effective for fluorination. This fluorination occurred in a step-by-step manner, and the reactivity difference between the first and second fluorinations was very small. N,N′-Difluoro-2,2′-bipyridinium bis(tetrafluoroborate) (1b) is thus shown to be a highly reactive and easy-to-handle electrophilic fluorinating agent with the high effective fluorine content (103.3 g/kg) for preparing many fluoro organic compounds.

N-halogeno compounds. Part 18. 1-Alkyl-4-fluoro-1,4-diazoniabicyclo [2.2.2] octane salts: User-friendly site-selective electrophilic fluorinating agents of the N-fluoroammonium class

Methods of synthesis are described for a range of 1-alkyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts [R-N+(CH2CH2)3N+-F (X-)2, where R = CH3, CH2Cl, C2H5, CF3CH2, C8H17 and (X-)2 = (TfO-)2, (BF4-)2, (PF6-)2, (TfO-, BF4-), (TfO-, PF6-), (TfO-, FSO3-)] by direct fluorination (with neat F2 at ≤20 mmHg or F2-N2 blends at 1 atm pressure) of monoquaternary salts of 1,4-diazabicyclo[2.2.2]octane [R-+N(CH2CH2)3N X-] or their 1:1 adducts with boron trifluoride, phosphorus pentafluoride, or sulfur trioxide in acetonitrile at ca - 35°C. The results of site-selective electrophilic fluorination of diethyl sodio(phenyl)malonate [→ PhCF(CO2Et)2], 1-morpholinocyclohexene (→ 2-fluorocyclohexanone), phenol (→ 2- and 4-FC6H4OH), 1- and 2-hydroxynaphthalene (→ 2- and 4-FC10H6OH, and 1-FC10H6OH and 1,1-difluoro-2-oxo-1,2-dihydronaphthalene, respectively), acetanilide (→ 2- and 4-FC6H4NHCOCH3), anisole (→ 2- and 4-FC6H4OCH3) and sodium benzenesulfinate (→ PhSO2F) with these N-fluoroammonium salts are presented.

N-Halogeno compounds. Part 15. Synthesis of N-fluoroquinuclidinium salts via direct fluorination of quinuclidine-Lewis acid adducts, and a comparison of their "F+" transfer capabilities

Fluorine smoothly attacks quinuclidine-trifluoroborane, quinuclidine-pentafluorophosphorane, and quinuclidine-sulfur trioxide in acetonitrile at -35 °C to give the corresponding N-fluoroquinuclidinium salts NFQ+X- (X- =BF4-, PF6-, and FSO3- respectively; Q = quinuclidine). Like its tetrafluoroborate analogue (NFQ+BF4-), the hexafluorophosphate NFQ+PF6- can also be prepared by direct fluorination of quinuclidine in the presence of the appropriate sodium salt (NaPF6). An alternative route to the tetrafluoroborate involves treatment of NFQ+F- with boron trifluoride. A comparative study of site-specific electrophilic fluorination of methoxybenzene [ → 1-fluoro2-and 4-methoxybenzene], 2-hydroxynaphthalene ( → 1-fluoro-2-hydroxynaphthalene and 1,1-difluoro-2-oxo-1,2-dihydronaphthalene), 2-nitropropan-2-yl-lithium ( → 2-fluoro-2-nitropropane) and diethyl sodio (phenyl) malonate [ → diethyl fluoro(phenyl) malonate] with all of the NFQ+X- salts mentioned above, plus the triflate (X- = CF3SO3-), revealed that the hexafluorophosphate and triflate are the most easily-handled and effective reagents.