Nitryl cyanide

Nitryl cyanide is an energetic chemical compound with the formula NCNO₂. Nitryl cyanide is a possible precursor to the theoretical explosive 2,4,6-trinitro-1,3,5-triazine.^[1][2]

Nitryl cyanide

Names
IUPAC name Nitroformonitrile
Other names Nitric cyanide
Identifiers
CAS Number	105879-05-8
3D model (JSmol)	Interactive image
PubChem CID	15798559
InChI InChI=1S/CN2O2/c2-1-3(4)5 Key: PLXPTFQGYWXIEA-UHFFFAOYSA-N
SMILES [O-][N+](=O)C#N
Properties
Chemical formula	CN2O2
Molar mass	72.023 g·mol−1
Appearance	Colourless liquid
Density	1.24 g ml−1 (−79 °C)
Melting point	−85 °C (−121 °F; 188 K)
Boiling point	7 °C (45 °F; 280 K)
Solubility in water	Reacts with water
Thermochemistry
Std enthalpy of formation (ΔfH⦵298)	212 kJ mol−1
Related compounds
Related compounds	Nitrile isocyanide (CNNO2)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Synthesis

Nitryl cyanide was first synthesized in 2014. The reaction of nitronium tetrafluoroborate with tert-butyldimethylsilyl cyanide at −30 °C produces nitryl cyanide, with tert-butyldimethylsilyl fluoride and boron trifluoride as byproducts.^[1]

NO₂BF₄ + t−BuMe₂SiCN → NCNO₂ + t−BuMe₂SiF + BF₃

The conversion of this method is only 50%, and using an excess of tert-butyldimethylsilyl causes the yield to drop even further.^[1]