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Difluoromethyl azide 1.2 M solution in DME

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  • IUPAC Name: Azidodifluoromethane
  • Synonyms: HCF2N3, Difluoromethylazide, Difluoromethyl azide
  • CAS: 41796-84-3
  • Smiles: [H]C(F)(N=[N+]=[N-])F
  • Chemical formula: CHF2N3
  • Molecular weight: 93.04

In 2018, CF Plus Chemicals and the group of Dr. Beier at IOCB Prague disclosed a convenient method of preparation of difluoromethylazide.

Difluoromethyl azide shares practically the same reactivity as trifluoromethyl azide in copper catalysed alkyne-azide cycloadditions, providing expedient access to five-membered N-CF2H heterocycles which are highly attractive for medicinal chemistry discovery programmes. Difluoromethyl azide provides similar synthetic benefits as other fluoroalkyl azides – a broad substrate scope of regiochemically defined N-difluoromethyl azoles can be accessed in a much simpler manner than with other synthetic routes.

Besides the established copper catalyzed alkyne-azide cycloadditon, difluoromethylazide was shown to undergo an enamine mediated azide-ketone [3+2] cycloadditons, affording the corresponding N-CF2H triazoles.

References:

1) Voltrová S., Putovný I., Matoušek V., Klepetářová B., Beier P.: Reintroducing Azidodifluoromethane: Synthesis, Stability and [3 + 2] Cycloadditions