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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 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.

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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Certificates of Analysis (COA)

Lot/Batch Number
WXBF2512V
WXBF0589V
WXBD7959V
MKCR9380
MKCR5622

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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)
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
Oxidative ring opening of 2, 5-diarylfurans by Selectfluor
Blank SJ and Stephens CE
Tetrahedron Letters, 47(38), 6849-6850 (2006)
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Global Trade Item Number

SKUGTIN
439479-25G04061832246093
439479-5G04061832246109
439479-100G04061832246086