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
Identifiers
3D model (JSmol)
  • InChI=1S/CN2O2/c2-1-3(4)5
    Key: PLXPTFQGYWXIEA-UHFFFAOYSA-N
  • [O-][N+](=O)C#N
Properties
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)
Reacts with water
Thermochemistry
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]

References

  1. Rahm, Martin; Bélanger-Chabot, Guillaume; Haiges, Ralf; Christe, Karl O. (2014-07-01). "Nitryl Cyanide, NCNO2". Angewandte Chemie International Edition. 53 (27): 6893–6897. doi:10.1002/anie.201404209. PMID 24861214.
  2. Zhou, Ming-Ming; Xiang, Dong (2022-05-29). "Theoretical Prediction of Structures and Properties of 2,4,6-Trinitro-1,3,5-Triazine (TNTA) Green Energetic Materials from DFT and ReaxFF Molecular Modeling". Materials. 15 (11): 3873. Bibcode:2022Mate...15.3873Z. doi:10.3390/ma15113873. ISSN 1996-1944. PMC 9182073. PMID 35683171.
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