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439479

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

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About This Item

Empirical Formula (Hill Notation):
C7H14B2ClF9N2
CAS Number:
140681-55-6
Molecular Weight:
354.26
UNSPSC Code:
12352101
NACRES:
NA.22
PubChem Substance ID:
24867509
MDL number:
MFCD00142607
Beilstein/REAXYS Number:
5368649
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form

powder

Quality Segment

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.

sustainability

Greener Alternative Product

concentration

>95% in F+ active

mp

260 °C (lit.)

functional group

chloro

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

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.

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk

WGK 2

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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