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Sigma-Aldrich

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

greener alternative

>95% in F+ active

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Synonym(s):
N-Chloromethyl-N′-fluorotriethylenediammonium bis(tetrafluoroborate), F-TEDA
Empirical Formula (Hill Notation):
C7H14B2ClF9N2
CAS Number:
140681-55-6
Molecular Weight:
354.26
Beilstein:
5368649
MDL number:
MFCD00142607
PubChem Substance ID:
24867509
NACRES:
NA.22

form

powder

Quality Level

200

reaction suitability

reagent type: catalyst
reagent type: oxidant
reaction type: C-H Activation

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

concentration

>95% in F+ active

mp

260 °C (lit.)

greener alternative category

Aligned,

storage temp.

2-8°C

SMILES string

F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2

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

InChI key

TXRPHPUGYLSHCX-UHFFFAOYSA-N

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General description

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product is a fluorine donor also called Selectfluor and has been enhanced for catalysis. Find details here.

Application

1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) is an electrophilic fluorinating reagent used for greener fluorination of acetoacetamides in PEG-400.
Catalyst-free and highly selective electrophilic mono-fluorination of acetoacetamides: facile and efficient preparation of 2-fluoroacetoacetamides in PEG-400

It can be used:
  • As a highly effective and versatile source of electrophilic fluorine.
  • As a fluorinating reagent that effects oxidative ring opening of 2,5-diarylfurans to cis-1,4-enediones.
  • For direct fluorination of silyl ketene acetals leading to the formation of α-fluoro-α-arylcarboxylic acids.
  • As an electrophilic fluorinating reagent used. e.g. in the preparation of fluorinated acylsilanes.

Other Notes

First application of ionic liquids in electrophilic fluorination of arenes; Selectfluor (F-TEDA-BF4) for “green” fluorination.

Citation

A review.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302 - H317 - H318 - H412

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Dam. 1 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Tetrahedron Letters, 47, 7641-7641 (2006)
Rajendra P Singh et al.
Accounts of chemical research, 37(1), 31-44 (2004-01-21)
Synthetic and structural aspects of organofluorine compounds continue to be the focal points of vigorous research activities, as evidenced by the appearance of a large number of publications. Among the various useful methodologies for the introduction of fluorine into organic
Oxidative ring opening of 2, 5-diarylfurans by Selectfluor
Blank SJ and Stephens CE
Tetrahedron Letters, 47(38), 6849-6850 (2006)
Paul T Nyffeler et al.
Angewandte Chemie (International ed. in English), 44(2), 192-212 (2004-12-04)
The replacement of hydrogen atoms with fluorine substituents in organic substrates is of great interest in synthetic chemistry because of the strong electronegativity of fluorine and relatively small steric footprint of fluorine atoms. Many sources of nucleophilic fluorine are available
Electrophilic NF Fluorinating Agents.
G. Sankar Lal et al.
Chemical reviews, 96(5), 1737-1756 (1996-08-01)
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Fluorinating Reagents

The importance of selectively fluorinating compounds in medicinal chemistry, biology, and organic synthesis is well appreciated and provides a major impetus to the discovery of new and mild fluorinating agents that can operate safely and efficiently.

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