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	1.84 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.^[3] Several synthesis routes are known, and bulk production of several hundred kilogram batches has been demonstrated at Los Alamos National Laboratory.^[4]^[1]^[5]

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.^[6]

References

^ ^a ^b ^c 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 978-94-024-1199-7.293-307&rft.date=2018&rft_id=info:doi/10.1007/978-94-024-1201-7_11&rft.isbn=978-94-024-1199-7&rft.aulast=Viswanath&rft.aufirst=Dabir S.&rft.au=Ghosh, Tushar K.&rft.au=Boddu, Veera M.&rfr_id=info:sid/en.wikipedia.org:1,3,3-Trinitroazetidine" class="Z3988">
^ 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. doi:10.1021/jo00296a066.2920-2924&rft.date=1990&rft_id=info:doi/10.1021/jo00296a066&rft.aulast=Archibald&rft.aufirst=T. G&rft.au=Gilardi, Richard&rft.au=Baum, K&rft.au=George, Clifford&rfr_id=info:sid/en.wikipedia.org:1,3,3-Trinitroazetidine" class="Z3988">
^ 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)10013-7.2–3&rft.pages=143-146&rft.date=1998-01&rft_id=info:doi/10.1016/S0956-053X(97)10013-7&rft_id=info:bibcode/1998WaMan..17..143C&rft.aulast=Coburn&rft.aufirst=Michael D.&rft.au=Hiskey, Michael A.&rft.au=Archibald, Thomas G.&rfr_id=info:sid/en.wikipedia.org:1,3,3-Trinitroazetidine" class="Z3988">
^ 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 98003295.219-239&rft.date=2001-06-01&rft_id=info:doi/10.1080/07370650108216127&rft_id=https://api.semanticscholar.org/CorpusID:98003295#id-name=S2CID&rft.issn=0737-0652&rft_id=info:bibcode/2001JEnM...19..219J&rft.aulast=Jalový&rft.aufirst=Zdenek&rft.au=Zeman, Svatopluk&rft.au=Suceska, Muhamed&rft.au=Vávra, Pave&rft.au=Dudek, Kamil&rft.au=Rajic, Masa&rfr_id=info:sid/en.wikipedia.org:1,3,3-Trinitroazetidine" class="Z3988">
^ 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)61673-8.6677-6680&rft.date=1993&rft_id=info:doi/10.1016/S0040-4039(00)61673-8&rft.aulast=Axenrod&rft.aufirst=Theodore&rft.au=Watnick, Clara&rft.au=Yazdekhasti, Hamid&rft.au=Dave, Paritosh R&rfr_id=info:sid/en.wikipedia.org:1,3,3-Trinitroazetidine" class="Z3988">

[book-1] 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 978-94-024-1199-7.293-307&rft.date=2018&rft_id=info:doi/10.1007/978-94-024-1201-7_11&rft.isbn=978-94-024-1199-7&rft.aulast=Viswanath&rft.aufirst=Dabir S.&rft.au=Ghosh, Tushar K.&rft.au=Boddu, Veera M.&rfr_id=info:sid/en.wikipedia.org:1,3,3-Trinitroazetidine" class="Z3988">

[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. doi:10.1021/jo00296a066.2920-2924&rft.date=1990&rft_id=info:doi/10.1021/jo00296a066&rft.aulast=Archibald&rft.aufirst=T. G&rft.au=Gilardi, Richard&rft.au=Baum, K&rft.au=George, Clifford&rfr_id=info:sid/en.wikipedia.org:1,3,3-Trinitroazetidine" class="Z3988">

[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)10013-7.2–3&rft.pages=143-146&rft.date=1998-01&rft_id=info:doi/10.1016/S0956-053X(97)10013-7&rft_id=info:bibcode/1998WaMan..17..143C&rft.aulast=Coburn&rft.aufirst=Michael D.&rft.au=Hiskey, Michael A.&rft.au=Archibald, Thomas G.&rfr_id=info:sid/en.wikipedia.org:1,3,3-Trinitroazetidine" class="Z3988">

[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 98003295.219-239&rft.date=2001-06-01&rft_id=info:doi/10.1080/07370650108216127&rft_id=https://api.semanticscholar.org/CorpusID:98003295#id-name=S2CID&rft.issn=0737-0652&rft_id=info:bibcode/2001JEnM...19..219J&rft.aulast=Jalový&rft.aufirst=Zdenek&rft.au=Zeman, Svatopluk&rft.au=Suceska, Muhamed&rft.au=Vávra, Pave&rft.au=Dudek, Kamil&rft.au=Rajic, Masa&rfr_id=info:sid/en.wikipedia.org:1,3,3-Trinitroazetidine" class="Z3988">

[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)61673-8.6677-6680&rft.date=1993&rft_id=info:doi/10.1016/S0040-4039(00)61673-8&rft.aulast=Axenrod&rft.aufirst=Theodore&rft.au=Watnick, Clara&rft.au=Yazdekhasti, Hamid&rft.au=Dave, Paritosh R&rfr_id=info:sid/en.wikipedia.org:1,3,3-Trinitroazetidine" class="Z3988">

[3]

[4]

[1]

[5]

[2]

[6]