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1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)_Molecular_structure_CAS_140681-55-6)
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1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)

Catalog No. L17003 Name Alfa Aesar
CAS Number 140681-55-6 Website
M. F. C7H14B2ClF9N2 Telephone
M. W. 354.2600888 Fax
Purity 98+% Email
Storage Chembase ID: 7710

SYNONYMS

Title
1-氯甲基-4-氟-1,4-重氮化二环2.2.2辛烷双(四氟硼酸盐)
IUPAC name
4-(chloromethyl)-1-fluoro-1,4-diazabicyclo[2.2.2]octane-1,4-diium; bis(tetrafluoroboranuide)
IUPAC Traditional name
4-(chloromethyl)-1-fluoro-1,4-diazabicyclo[2.2.2]octane-1,4-diium ditetrafluoroborate
Synonyms
SELECTFLUOR Fluorinating Reagent
F-TEDA-BF4

DATABASE IDS

EC Number 414-380-4
CAS Number 140681-55-6
MDL Number MFCD00142607

PROPERTIES

Purity 98+%
Melting Point ca 250°C dec.
GHS Pictograms GHS05
GHS Pictograms GHS07
GHS Hazard statements H318-H302-H317-H313-H402-H412
European Hazard Symbols X
GHS Precautionary statements P261-P280-P273-P270-P305+P351+P338
Risk Statements 22-41-43-52/53
Safety Statements 21-26-36/37/39-61
TSCA Listed
Hazard Class 4.2
UN Number UN3088
Packing Group II

DETAILS

REFERENCES

  • SELECTFLUOR is a registered trademark of Air Products & Chemicals Inc.
  • 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 application to N-fluorination of amines, see: Chem. Commun., 1196 (2001). Review of mechanistic insight and applications of the reagent: Angew. 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).
  • 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).
  • 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).