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  • 439479 - 1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)

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439479 Sigma-Aldrich

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

Green Alternative

>95% in F+ active

Synonym: N-Chloromethyl-N′-fluorotriethylenediammonium bis(tetrafluoroborate), F-TEDA

  • CAS Number 140681-55-6

  • Empirical Formula (Hill Notation) C7H14B2ClF9N2

  • Molecular Weight 354.26

  •  Beilstein/REAXYS Number 5368649

  •  MDL number MFCD00142607

  •  PubChem Substance ID 24867509

  •  NACRES NA.22

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Properties

Related Categories 12 Principles Aligned Products, C-H Activation, Catalysis and Inorganic Chemistry, Chemical Synthesis, Fluorination,
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

Description

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

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

Packaging

5, 25, 100 g in poly bottle

Other Notes

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

Citation

A review.

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Personal Protective Equipment 
RIDADR 
UN 3088 4.2 / PGII
WGK Germany 
WGK 2
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

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 fluorinat...
Aldrich ChemFiles 2006, 6.2, 5.
Keywords: Fluorinations, Medicinal chemistry, Metathesis, Organic synthesis

Reagents for Fluorination

The trifluoromethyl substituent has long been recognized for the positive influence it can have on the biological activity of molecules. Professor William Dolbier, Jr. (University of Florida) has dev...
Aldrich ChemFiles 2007, 7.1, 11.

Peer-Reviewed Papers
15

References

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