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Selectfluor information


Selectfluor
Names
IUPAC name
1-(Chloromethyl)-4-fluoro-1,4-diazabicyclo[2.2.2]octane-1,4-diium ditetrafluoroborate
Other names
F-TEDA, N-Chloromethyl-N-fluorotriethylenediammonium bis(tetrafluoroborate)
1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)
Identifiers
CAS Number
  • 140681-55-6 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 2007047 ☒N
ECHA InfoCard 100.101.349 Edit this at Wikidata
EC Number
  • 414-380-4
PubChem CID
  • 2724933
UNII
  • 4P1ZA6R76D checkY
CompTox Dashboard (EPA)
  • DTXSID0073112 Edit this at Wikidata
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 190 °C (374 °F; 463 K) decomposes >80 °C, exact m.p. is uncertain[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

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.[1]

  1. ^ a b Banks, R. Eric; Murtagh, Vincent; An, Ilhwan; Maleczka, Robert E. (2007). "1-(Chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane Bis(tetrafluoroborate)". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rc116.pub2. ISBN 978-0471936237.

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Selectfluor

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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...

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DABCO

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reactions of aldehydes and unsaturated ketones and aldehydes. The reagent Selectfluor is derived by alkylation of DABCO with dichloromethane following by treatment...

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Electrophilic fluorination

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N-fluoro-o-benzenedisulfonimide (NFOBS), N-fluorobenzenesulfonimide (NFSI), and Selectfluor. The mechanism of electrophilic fluorination remains controversial. At...

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Xenon difluoride

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salts, useful as fluorine transfer reagents in organic synthesis (e.g., Selectfluor), from the corresponding tertiary amine: [R–+N(CH2CH2)3N:][BF− 4] + XeF2...

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Electrophilic halogenation

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fluorination is possible with F2/N2 (10%), XeF2, or N-F reagents like Selectfluor, these methods are seldom used, due to the formation of isomeric mixtures...

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Menshutkin reaction

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over several hours to give the quaternized product (see the article on Selectfluor). Due to steric hindrance and unfavorable electronic properties, chloroform...

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Tetrafluoroborate

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Fe(C 5H 5)+ 2, and other cationic metallocenes. [Ni(CH3CH2OH)6](BF4)2. Selectfluor, a fluorination agent, and other N–F electrophilic fluorine sources....

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Asymmetric counteranion directed catalysis

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chiral counteranion. In the example below, the fluorinating reagent Selectfluor exhibits extremely limited solubility in nonpolar solvents and is therefore...

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Radical fluorination

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arylsilanes, and act as an atomic fluorine source to furnish aryl fluorides. Selectfluor and N-fluorobenzenesulfonimide (NFSI) are traditionally used as electrophilic...

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