CF2CF2-Chemistry

One of the main parts of the company´s portfolio are reagents and building blocks that install the CF2CF2X moiety.

Compared to processes like fluorination and trifluoromethylation, the chemistry of -CF2CF2H and -CF2CF2-scaffolds is much less established.

Incorporation of CF2CF2 as an internal perfluoroalkanediyl (IPF) fragment has been shown to cause significant changes in substrate-receptor binding properties as shown in the pionieering work of DiMagno[1] and Linclau[2] on heavily fluorinated sugars. Introducing the concept of „polar hydrofobicity“, the presence of CF2CF2 moiety can be viewed as a potentially powerful tool how to further enhance molecular recognition within the receptor. Substitution of polar hydrophilic groups by fluorine atoms while retaining the shape of molecule can strengthen the specific binding at the sites of the receptor that have the capabality to stabilize the negative periphery of the C-F dipole.

CF2CF2 effects 1

Advantages of CF2CF2

CF2CF2 as an internal perfluoroalkanediyl fragment can have other beneficial roles:

  • as a part of a cycle it can generate a substantial dipole moment
  • it can replace otherwise metabolically labile alkanediyl fragments
  • it can behave as a conformational lock
  • it can impart increased oxidation stability to pesticides, making them less vulnerable to attack by OH radicals
  • CF2CF2 bridging unit could bring beneficial properties to fluorinated liquid crystals

Our CF2CF2 portfolio

Our portfolio contains 4 classes of compounds that help to install the CF2CF2 Fragments:

fluoroalkylbromides button Fluoroalkylsilanes button extended Togni reagents buttonFluoroalkyl carboxylic acids button

 

 

 

 

 

References

  1. J. C. Biffinger, H. W. Kim, S. G. DiMagno, ChemBioChem 2004, 5, 622-627.
  2. A. J. Boydell, V. Vinader, B. Linclau, Angew. Chem. Int. Ed. 2004, 43, 5677-5679.

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