1,3,3-Trinitroazetidine

1,3,3-Trinitroazetidine
Names
	Preferred IUPAC name 1,3,3-Trinitroazetidine
	Other names TNAZ
Identifiers
CAS Number	97645-24-4 ;
3D model (JSmol)	Interactive image;
ChemSpider	7969893 ;
PubChem CID	9794126;
UNII	41T9FAH22H ;
CompTox Dashboard (EPA)	DTXSID20913764 ;
	InChI InChI=1S/C3H4N4O6/c8-5(9)3(6(10)11)1-4(2-3)7(12)13/h1-2H2 Key: ZCRYIJDAHIGPDQ-UHFFFAOYSA-N;
	SMILES C1C(CN1[N+](=O)[O-])([N+](=O)[O-])[N+](=O)[O-];
Properties
Chemical formula	C3H4N4O6
Molar mass	192.087 g·mol−1
Appearance	Pale yellow crystals
Density	1.86 g⁄cm3
Melting point	101 °C (214 °F; 374 K)
Boiling point	252 °C (486 °F; 525 K)
Structure
Crystal structure	Orthorhombic
Explosive data
Detonation velocity	9597 m/s
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). (what is ?) Infobox references

1,3,3-Trinitroazetidine (TNAZ) is an explosive heterocyclic compound that has been considered as a potential replacement for TNT because of its low melting point (101 °C) and good thermal stability (up to 240 °C). TNAZ was first synthesized by Archibald et al. in 1990. Several synthesis routes are known, and bulk production of several hundred kilogram batches has been demonstrated at Los Alamos National Laboratory.

Properties

The compound crystallizes in an orthorhombic lattice with the space group Pbca. Thermolysis occurs starting around 240 °C - 250 °C with decomposition products that include nitrogen dioxide, nitric oxide, nitrous acid, carbon dioxide, and formaldehyde. It has a heat of decomposition of 6343 kJ/kg, and a detonation pressure of 36.4 GPa.

References

1 2 3 Viswanath, Dabir S.; Ghosh, Tushar K.; Boddu, Veera M. (2018). "1,3,3-Trinitroazetidine (TNAZ)". Emerging Energetic Materials: Synthesis, Physicochemical, and Detonation Properties. pp. 293–307. doi:10.1007/978-94-024-1201-7_11. ISBN 978-94-024-1199-7.
↑ Simpson, R.L.; Garza, R.G.; Foltz, M.F.; Ornellas, D.L.; Utriew, P.A. (14 December 1994). Characterization of TNAZ (PDF) (Technical report). Office of Scientific and Technical Information (OSTI). doi:10.2172/71573. OSTI 71573.
↑ Archibald, T. G; Gilardi, Richard; Baum, K; George, Clifford (1990). "Synthesis and x-ray crystal structure of 1,3,3-trinitroazetidine". The Journal of Organic Chemistry. 55 (9): 2920–2924. Bibcode:1990JOrgC..55.2920A. doi:10.1021/jo00296a066.
↑ Coburn, Michael D.; Hiskey, Michael A.; Archibald, Thomas G. (January 1998). "Scale-up and waste-minimization of the Los Alamos process for 1,3,3-trinitroazetidine (TNAZ)". Waste Management. 17 (2–3): 143–146. Bibcode:1998WaMan..17..143C. doi:10.1016/S0956-053X(97)10013-7.
↑ Jalový, Zdenek; Zeman, Svatopluk; Suceska, Muhamed; Vávra, Pave; Dudek, Kamil; Rajic, Masa (1 June 2001). "1,3,3-trinitroazetidine (TNAZ). Part I. Syntheses and properties". Journal of Energetic Materials. 19 (2): 219–239. Bibcode:2001JEnM...19..219J. doi:10.1080/07370650108216127. ISSN 0737-0652. S2CID 98003295.
↑ Axenrod, Theodore; Watnick, Clara; Yazdekhasti, Hamid; Dave, Paritosh R (1993). "Synthesis of 1,3,3-trinitroazetidine". Tetrahedron Letters. 34 (42): 6677–6680. doi:10.1016/S0040-4039(00)61673-8.

[book-1] 1 2 3 Viswanath, Dabir S.; Ghosh, Tushar K.; Boddu, Veera M. (2018). "1,3,3-Trinitroazetidine (TNAZ)". Emerging Energetic Materials: Synthesis, Physicochemical, and Detonation Properties. pp. 293–307. doi:10.1007/978-94-024-1201-7_11. ISBN 978-94-024-1199-7.

[2] Simpson, R.L.; Garza, R.G.; Foltz, M.F.; Ornellas, D.L.; Utriew, P.A. (14 December 1994). Characterization of TNAZ (PDF) (Technical report). Office of Scientific and Technical Information (OSTI). doi:10.2172/71573. OSTI 71573.

[arch-3] Archibald, T. G; Gilardi, Richard; Baum, K; George, Clifford (1990). "Synthesis and x-ray crystal structure of 1,3,3-trinitroazetidine". The Journal of Organic Chemistry. 55 (9): 2920–2924. Bibcode:1990JOrgC..55.2920A. doi:10.1021/jo00296a066.

[4] Coburn, Michael D.; Hiskey, Michael A.; Archibald, Thomas G. (January 1998). "Scale-up and waste-minimization of the Los Alamos process for 1,3,3-trinitroazetidine (TNAZ)". Waste Management. 17 (2–3): 143–146. Bibcode:1998WaMan..17..143C. doi:10.1016/S0956-053X(97)10013-7.

[5] Jalový, Zdenek; Zeman, Svatopluk; Suceska, Muhamed; Vávra, Pave; Dudek, Kamil; Rajic, Masa (1 June 2001). "1,3,3-trinitroazetidine (TNAZ). Part I. Syntheses and properties". Journal of Energetic Materials. 19 (2): 219–239. Bibcode:2001JEnM...19..219J. doi:10.1080/07370650108216127. ISSN 0737-0652. S2CID 98003295.

[Axenrod-6] Axenrod, Theodore; Watnick, Clara; Yazdekhasti, Hamid; Dave, Paritosh R (1993). "Synthesis of 1,3,3-trinitroazetidine". Tetrahedron Letters. 34 (42): 6677–6680. doi:10.1016/S0040-4039(00)61673-8.