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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+%

CAS-Nummer
140681-55-6
Synonyme
F-TEDA-BF4

Größe Preis ($) Menge Verfügbarkeit
5g 38,34
25g 124,20
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1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate), 98+%

MDL
MFCD00142607
EINECS
414-380-4

Chemische Eigenschaften

Formel
C7H14B2ClF9N2
Molmasse
354.26
Schmelzpunkt
ca 250° dec.
Löslichkeit
Soluble in water, acetonitrile, alcohol, acetone, dimethylformamide, pyridine and dimethylsulfoxide.

Anwendungen

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.

Bemerkungen

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

Literaturverweise

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.

GHS Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H318-H302-H317-H313-H402-H412

Causes serious eye damage. Harmful if swallowed. May cause an allergic skin reaction. May be harmful in contact with skin. Harmful to aquatic life. Harmful to aquatic life with long lasting effects.

Sicherheitshinweise: P261-P273-P280-P270-P305+P351+P338

Avoid breathing dust/fume/gas/mist/vapours/spray. Avoid release to the environment. Wear protective gloves/protective clothing/eye protection/face protection. Do not eat, drink or smoke when using this product. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

Weitere Referenzen

Gefahrenklasse
4.2
Verpackungsgruppe
II
Harmonized Tariff Code
2933.59
TSCA
Yes

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