Trinitrotriazine

Trinitrotriazine
Names
	Preferred IUPAC name 2,4,6-Trinitro-1,3,5-triazine
Identifiers
CAS Number	140218-59-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	15188373 ;
PubChem CID	21997109;
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;
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

The printable version is no longer supported and may have rendering errors. Please update your browser bookmarks and please use the default browser print function instead.

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 neutral 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, more commonly known as RDX. Propellants, Explosives, Pyrotechnics. December 2008; 33(6):443-447.

This article about theoretical chemistry is a stub. You can help Wikipedia by expanding it.

[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, more commonly known as RDX. Propellants, Explosives, Pyrotechnics. December 2008; 33(6):443-447.

[1]

[2]

[3]

[4]

[5]

See also

References