140681-68-1

Basic information

• Product Name: 1-CHLOROMETHYL-4-FLUORO-1,4-DIAZONIABICYCLO[2.2.2]OCTANE BIS(TRIFLUOROMETHANESULFONATE)
• Synonyms: F-TEDA-OTF;1-CHLOROMETHYL-4-FLUORO-1,4-DIAZONIABICYCLO[2.2.2]OCTANE BIS(TRIFLUOROMETHANESULFONATE);1-(CHLOROMETHYL)-4-FLUORO-1,4-DIAZONIABICYCLO[2.2.2]OCTANE BIS(TRIFLUOROMETHANESULPHONATE);1-(Chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tfl.methanesulphonate)
• CAS NO: 140681-68-1
• Molecular Formula: 2CF₃O₃S*C₇H₁₄ClFN₂
• Molecular Weight: 478.79
• Mol File: 140681-68-1.mol

Chemical Properties

• Melting Point: 165°C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: 1-CHLOROMETHYL-4-FLUORO-1,4-DIAZONIABICYCLO[2.2.2]OCTANE BIS(TRIFLUOROMETHANESULFONATE)(CAS DataBase Reference)
• NIST Chemistry Reference: 1-CHLOROMETHYL-4-FLUORO-1,4-DIAZONIABICYCLO[2.2.2]OCTANE BIS(TRIFLUOROMETHANESULFONATE)(140681-68-1)
• EPA Substance Registry System: 1-CHLOROMETHYL-4-FLUORO-1,4-DIAZONIABICYCLO[2.2.2]OCTANE BIS(TRIFLUOROMETHANESULFONATE)(140681-68-1)

Safety Data

• Hazard Codes: O
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 140681-68-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H14ClFN2.2CHF3O3S/c8-7-10-1-4-11(9,5-2-10)6-3-10;2*2-1(3,4)8(5,6)7/h1-7H2;2*(H,5,6,7)/q+2;;/p-2

Upstream product

• 33454-82-9 lithium trifluoromethanesulfonate 
• 141922-62-5 1-Chloromethyl-4-aza-1-azoniabicyclo<2.2.2>octane triflate 

Downstream Products

• 51417-63-1 1-fluoronaphthalen-2-ol 
• 51417-64-2 1,1-difluoro-1H-naphthalen-2-one 
• 7226-39-3 2-deoxy-2-fluoro-D-mannopyranose 
• 38711-37-4 2-deoxy-2-fluoro-β-D-glucopyranose 
• 7226-39-3 2-fluoro-2-deoxy-D-glucose 

Relevant articles and documents

Radiosynthesis and evaluation of [18F]Selectfluor bis(triflate)

(Figure Presented) Selectfluor, one of the most reactive and commonly used electrophilic fluorinating N-F reagents, has been radiolabeled with 18F. The resulting new [18F]-labeled N-F reagent is safe, nontoxic, and easy to handle. The combined use of [18F]Selectfluor bis(triflate) and AgOTf allows for the preparation of electron-rich 18F-aromatic compounds through a simple "shake and mix" protocol at room temperature (see scheme; SA=specific activtiy).

Metal-free18F-labeling of aryl-CF2H via nucleophilic radiofluorination and oxidative C-H activation

A metal-free and selective method to form [18F]aryl-CF2H through nucleophilic radiofluorination of benzyl (pseudo)halides and oxidative C-H activation of benzylic C-H bonds has been developed. The method is operationally simple and tolerates a variety of electron-neutral/deficient arenes and heteroarenes.

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.

1-Alkyl-4-fluoro-1,4-diazoniabicyclooctane Salts: a Novel Family of Electrophilic Fluorinating Agents

Members of a new series of solid, easily handled, storable, transportable, commercially viable, site-selective electrophilic fluorinating agents of the +N-F class (tradenamed Selectfluor reagents) have been synthesized via direct fluorination of monoquaternary salts of 1,4-diazabicyclooctane.