439479

Sigma-Aldrich

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

greener alternative

>95% in F+ active

Synonym(s):
N-Chloromethyl-N′-fluorotriethylenediammonium bis(tetrafluoroborate), F-TEDA
Empirical Formula (Hill Notation):
C7H14B2ClF9N2
CAS Number:
Molecular Weight:
354.26
Beilstein/REAXYS Number:
5368649
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

reaction suitability

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.)

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.

Packaging

5, 25, 100 g in poly bottle

Citation

A review.

Pictograms

CorrosionExclamation mark

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 3088 4.2 / PGII

WGK Germany

WGK 2

Certificate of Analysis
Certificate of Origin
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)
A novel general method for preparation of a-fluoro-a-arylcarboxylic acid. Direct fluorination of silyl ketene acetals with Selectfluor
Zhang F and Song JZ
Tetrahedron Letters, 47(43), 7641-7644 (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...
A general method for synthesis of trifluoroacetyltrialkyl (aryl) silanes and the Sakurai reaction of fluorinated acylsilanes with allyl silanes
Chung WJ and Welch JT
Journal of Fluorine Chemistry, 125(4), 543-548 (2004)
Articles
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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