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140681-55-6 - 1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate), 98+% - F-TEDA-BF4 - L17003 - Alfa Aesar

L17003 1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate), 98+%

Codice CAS

Dimensioni Prezzo ($) Quantità Disponibilità
5g 41,70
25g 135,00
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1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate), 98+%


Proprietà chimiche

Peso formula
Punto di fusione
ca 250° dec.
Soluble in water, acetonitrile, alcohol, acetone, dimethylformamide, pyridine and dimethylsulfoxide.


1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) is used as a reagent for electrophilic fluorination and also acts as a selective oxidizing agent. It is a highly effective and versatile source of electrophilic fluorine and also used in the synthesis of organofluorine.


Moisture sensitive. Incompatible with strong oxidizing agents, reducing agents, strong acids and bases.


SELECTFLUOR is a registered trademark of Air Products & Chemicals Inc.

Water- and organic-soluble reagent developed by R. E. Banks and co-workers for electrophilic fluorination of a variety of substrates under mild conditions: USP 5,086,178 (1992 to Air Products & Chemicals, Inc.); review: J. Fluorine Chem., 87, 1 (1998). In acetonitrile, activated aromatics can be fluorinated in good yield: J. Chem. Soc., Perkin 1., 2069 (1996). Less active substrates can be fluorinated in the presence of triflic acid: Israel J. Chem., 39, 207 (1999). In acetonitrile, vinylsilanes undergo fluorodesilylation to give vinyl fluorides with retention of configuration: Chem. Commun., 233 (2001).

Stabilized carbanions can be selectively mono- or difluorinated: J. Chem. Soc., Chem. Commun., 343 (1994); Tetrahedron, 51, 3587 (1995). Fluorinated steroids have been prepared from enol acetates or silyl enol ethers: J. Org. Chem., 58, 2791 (1993). 5-Fluoropyrimidine nucleosides can be obtained by treatment of protected nucleosides with the reagent in the presence of water or methanol, followed by elimination of the resulting fluorohydrin derivative: J. Org. Chem., 60, 7340 (1995).

For use in the synthesis of fluorinated carbohydrates by reaction with glycals, see: J. Am. Chem. Soc., 119, 11743 (1997); J. Org. Chem., 64, 5264 (1999).

For application to N-fluorination of amines, see: Chem. Commun., 1196 (2001). Review of mechanistic insight and applicatio ns of the reaAngew. Chem. Int Ed., 44, 192 (2005). Brief feature on uses in synthesis: Synlett, 807 (2006). Review of electrophilic N-F fluorinating agents: Chem. Rev., 96, 1737 (1996).

Laali, K. K.; Jamalian, A.; Zhao, C. Reaction of Selectfluor (F-TEDA-BF4) with chloromethylated-DABCO monocation salts (X= BF4, NTf2) and other nitrogen bases (Et3N; piperidine; basic ionic liquid); unexpected formation of symmetrical [N- H- N]+ trication salts. Tetrahedron Lett. 2014, 55 (49), 6643-6646.

Reddy, A. S.; Laali, K. K. Mild and selective α-fluorination of carbonyl compounds (ketones, 1, 3-diketones, β-ketoesters, α-nitroketones, and β-ketonitriles) with Selectfluor (F-TEDA-BF 4) in imidazolium ILs [BMIM/PF6 or BMIM/NTf2] with Brønsted-acidic IL [PMIM (SO3H)/OTf] as promoter. Tetrahedron Lett. 2015, 56 (41), 5495-5499.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H302-H318-H317

Harmful if swallowed. Causes serious eye damage. May cause an allergic skin reaction.

Dichiarazioni precauzionali: P260-P201-P280-P304+P340-P301+P312a-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Obtain special instructions before use. Wear protective gloves/protective clothing/eye protection/face protection. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF SWALLOWED: Dispose of contents/container in accordance with local/regional/national/international regulations.

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