140681-58-9

Basic information

• Product Name: 4-methyl-1,4-diazoniabicyclo<2.2.2>octane ditriflate
• Synonyms: 4-methyl-1,4-diazoniabicyclo<2.2.2>octane ditriflate
• CAS NO: 140681-58-9
• Molecular Weight: 426.358
• Mol File: 140681-58-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 4-methyl-1,4-diazoniabicyclo<2.2.2>octane ditriflate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methyl-1,4-diazoniabicyclo<2.2.2>octane ditriflate(140681-58-9)
• EPA Substance Registry System: 4-methyl-1,4-diazoniabicyclo<2.2.2>octane ditriflate(140681-58-9)

Safety Data

• Hazardous Substances Data: 140681-58-9(Hazardous Substances Data)

Upstream product

• 108-95-2 phenol 
• 140681-44-3 1-fluoro-4-methyl-1,4-diazoniabicyclo[2.2.2]octane bis(trifluoromethanesulfonate) 

Relevant articles and documents

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.