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
• Article Data: 4

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

Description

1-CHLOROMETHYL-4-FLUORO-1,4-DIAZONIABICYCLO[2.2.2]OCTANE BIS(TRIFLUOROMETHANESULFONATE) is a diazonium salt derivative with the molecular formula C7H10ClF4N2O6S2. It is characterized by the presence of a chloromethyl group, a fluorine atom, and a bis(trifluoromethanesulfonate) anion. 1-CHLOROMETHYL-4-FLUORO-1,4-DIAZONIABICYCLO[2.2.2]OCTANE BIS(TRIFLUOROMETHANESULFONATE) is known for its versatility in various chemical reactions due to the enhancing solubility and stability provided by the trifluoromethanesulfonate anion.
Used in Organic Synthesis:
1-CHLOROMETHYL-4-FLUORO-1,4-DIAZONIABICYCLO[2.2.2]OCTANE BIS(TRIFLUOROMETHANESULFONATE) is used as a reagent for the functionalization of aromatic compounds, particularly for the introduction of fluorine or chlorine atoms. This allows for the creation of new compounds with specific properties and applications.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 1-CHLOROMETHYL-4-FLUORO-1,4-DIAZONIABICYCLO[2.2.2]OCTANE BIS(TRIFLUOROMETHANESULFONATE) is used as a key intermediate in the synthesis of various drugs. Its ability to functionalize aromatic compounds makes it a valuable tool in the development of new medications with improved efficacy and safety profiles.
Used in Agrochemical Synthesis:
Similarly, in the agrochemical industry, 1-CHLOROMETHYL-4-FLUORO-1,4-DIAZONIABICYCLO[2.2.2]OCTANE BIS(TRIFLUOROMETHANESULFONATE) is utilized as a reagent for the synthesis of agrochemicals. Its functionalization capabilities contribute to the development of more effective and targeted pesticides and other agricultural products.
Used as a Biocide in Industrial Applications:
1-CHLOROMETHYL-4-FLUORO-1,4-DIAZONIABICYCLO[2.2.2]OCTANE BIS(TRIFLUOROMETHANESULFONATE) also exhibits antimicrobial properties, making it suitable for use as a biocide in various industrial applications. This can help prevent the growth of harmful microorganisms in different settings, contributing to improved safety and hygiene.

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).

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.