Trinitrotriazine

Trinitrotriazine
Names
	IUPAC name 2,4,6-Trinitro-1,3,5-triazine
Identifiers
CAS Number	140218-59-3 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	15188373 ;
CompTox Dashboard (EPA)	DTXSID10621341 ;
	InChI InChI=1S/C3N6O6/c10-7(11)1-2(8(12)13)4-6-5-3(1)9(14)15 Key: QHHATGLDAJAQBL-UHFFFAOYSA-N ;
	SMILES O=[N+]([O-])C1=NC([N+]([O-])=O)=NC([N+]([O-])=O)=N1; O=N(=O)c1nnnc(c1N(=O)=O)N(=O)=O;
Properties
Chemical formula	C3N6O6
Molar mass	216.069 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Trinitrotriazine, or 2,4,6-trinitro-1,3,5-triazine, is a theoretical explosive compound. Synthesis of this compound has been elusive despite its simple structure,^[1]^[2] as conventional nitration of triazine becomes increasingly more difficult as more nitro groups are added. A successful route would more likely proceed by trimerisation of nitryl cyanide.^[3] The precursor, nitryl cyanide, was first synthesized by Rahm et al in 2014.^[4]

Trinitrotriazine has a perfect oxygen balance, potentially making it a very powerful explosive, though calculations predict it would be fairly unstable and inferior to the related compound 3,6-dinitro-1,2,4,5-tetrazine.^[5]

References

^ G. D. Hartman, R. D. Hartman and J. E. Schwering. Tetrahedron Letters. 1983; 24: 1011.
^ M. D. Coburn, C. L. Coon, H. H. Hayden and A. R. Mitchell. Synthesis. 1986: 490.
^ Korkin AA. Bartlett RJ. Theoretical Prediction of 2,4,6-Trinitro-1,3,5-triazine (TNTA). A New, Powerful, High-Energy Density Material? Journal of the American Chemical Society. 1996; 118: 12244-12245.
^ Rahm, M., Bélanger-Chabot, G., Haiges, R. and Christe, K. O. (2014), Nitryl Cyanide, NCNO₂. Angew. Chem. Int. Ed., 53: 6893–6897
^ Jinshan Li. An Ab Initio Theoretical Study of 2,4,6-Trinitro-1,3,5-Triazine, 3,6-Dinitro-1,2,4,5-Tetrazine, and 2,5,8-Trinitro-Tri-s-Triazine. Propellants, Explosives, Pyrotechnics. December 2008; 33(6):443-447.

[1] G. D. Hartman, R. D. Hartman and J. E. Schwering. Tetrahedron Letters. 1983; 24: 1011.

[2] M. D. Coburn, C. L. Coon, H. H. Hayden and A. R. Mitchell. Synthesis. 1986: 490.

[3] Korkin AA. Bartlett RJ. Theoretical Prediction of 2,4,6-Trinitro-1,3,5-triazine (TNTA). A New, Powerful, High-Energy Density Material? Journal of the American Chemical Society. 1996; 118: 12244-12245.

[4] Rahm, M., Bélanger-Chabot, G., Haiges, R. and Christe, K. O. (2014), Nitryl Cyanide, NCNO₂. Angew. Chem. Int. Ed., 53: 6893–6897

[5] Jinshan Li. An Ab Initio Theoretical Study of 2,4,6-Trinitro-1,3,5-Triazine, 3,6-Dinitro-1,2,4,5-Tetrazine, and 2,5,8-Trinitro-Tri-s-Triazine. Propellants, Explosives, Pyrotechnics. December 2008; 33(6):443-447.

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See also

References