Selectfluor

Names

IUPAC name

1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane ditetrafluoroborate

Other names

F-TEDA, N-Chloromethyl-N-fluorotriethylenediammonium bis(tetrafluoroborate)

Identifiers

CAS Number

140681-55-6^Y

3D model (JSmol)

Interactive image

ChemSpider

2007047^N

ECHA InfoCard

100.101.349

EC Number

414-380-4

PubChem CID

2724933

InChI

InChI=1S/C7H14ClFN2.2BF4/c8-7-10-1-4-11(9,5-2-10)6-3-10;2*2-1(3,4)5/h1-7H2;;/q+2;2*-1^N

Key: TXRPHPUGYLSHCX-UHFFFAOYSA-N^N
InChI=1/C7H14ClFN2.2BF4/c8-7-10-1-4-11(9,5-2-10)6-3-10;2*2-1(3,4)5/h1-7H2;;/q+2;2*-1

Key: TXRPHPUGYLSHCX-UHFFFAOYAI

SMILES

[B-](F)(F)(F)F.[B-](F)(F)(F)F.C1C[N+]2(CC[N+]1(CC2)CCl)F

Properties

Chemical formula

C₇H₁₄B₂ClF₉N₂

Molar mass

354.26 g/mol

Appearance

colourless solid

Melting point

234

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

(what is ^YN ?)

Infobox references

1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) or Selectfluor, a trademark of Air Products and Chemicals, is a reagent in chemistry that is used as a fluorine donor. This compound is a derivative of the heterocycle DABCO . This colourless salt was first described in 1992 and has since been commercialized for use in organofluorine chemistry for electrophilic fluorination.

Selectfluor is synthesized by the N-alkylation of diazabicyclo[2.2.2]octane (DABCO) with dichloromethane, followed by ion exchange with sodium tetrafluoroborate (replacing the chloride counterion for the tetrafluoroborate). Finally, this salt is treated with elemental fluorine and sodium tetrafluoroborate:

The conventional source of "electrophilic fluorine", i.e. the equivalent to the superelectrophile F⁺, is gaseous fluorine, which requires specialised equipment for manipulation. Selectfluor reagent is a salt, the use of which requires only routine procedures. Like F₂, the salt delivers the equivalent of F⁺. It is mainly used in the synthesis of organofluorine compounds:

The ability of Selectfluor to transfer fluorine to alkyl radicals has recently been demonstrated.

Selectfluor reagent also serves as a strong oxidant, a property that is useful in other reactions in organic chemistry. Oxidation of alcohols and phenols. As applied to electrophilic iodination, Selectfluor reagent activates the I–I bond in I₂ molecule.

...
Wikipedia