Trinitrotriazine

Trinitrotriazine

Names
IUPAC name 2,4,6-Trinitro-1,3,5-triazine
Identifiers
CAS Number	140218-59-3
ChemSpider	15188373
Jmol interactive 3D	Image Image
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	216.07 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 has finally been synthetized.^[4]

It 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]

See also

• RDX (hexahydro-1,3,5-trinitro-1,3,5-triazine)

References

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.