Selectfluor

Also known as 1-chloromethyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane bis(tetrafluoroborate)

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 nucleophillic base DABCO. It is a colourless salt that tolerates air and even water. It has been commercialized for use for electrophilic fluorination.

Chemical data

Formula: C7H14B2ClF9N2
Molecular weight: 354.3 g/mol
IUPAC name: 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane ditetrafluoroborate

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Wikidata facts

Mass: 354.089

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chemical formula: C₇H₁₄B₂ClF₉N₂
canonical SMILES: [B-](F)(F)(F)F.[B-](F)(F)(F)F.C1C[N+]2(CC[N+]1(CC2)CCl)F
Commons category: Selectfluor

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Article

7 sections

Contents

Preparation
Mechanism of fluorination
Applications
Specialized applications
Related reagents
References
Patents

==Preparation== 550px|F-TEDA-BF4 synthesis Selectfluor is synthesized by the N-alkylation of [[DABCO|diazabicyclo[2.2.2]octane (DABCO)]] with dichloromethane in a Menshutkin reaction, followed by ion exchange with sodium tetrafluoroborate (replacing the chloride counterion for the tetrafluoroborate). The resulting salt is treated with elemental fluorine and sodium tetrafluoroborate: