Trinitroazetidine

The above compound, prepared as an intermediate to 1,3,3-trinitroazetidine for study as an explosive, decomposed explosively when heated above 120°C for distillation. Precautions when handling nitroazetidines are counselled. 

TNAZ (2.19) is also known as 1,3,3-trinitroazetidine (C3H4N406) and was first prepared in 1983 at Fluorochem Inc. It is reported to be more thermally stable than RDX but more reactive than HMX. Pure TNAZ is more shock sensitive than the explosives based on HMX but less sensitive than analogous PETN. It can be used as a castable explosive and as an ingredient in solid rocket and gun propellant. 

More chemistry directed towards the development of efficient routes to 1,3,3-trinitroazetidine has been published, including a full paper (95JOC1959) on the work given in a... 

An oxidation of the nitroso group in l-nitroso-3-nitroazetidine 122 by nitric acid in trifluoroacetic anhydride led to the synthesis of 1,3-dinitroazetidine 123 (Equation 33) <1998SC3949>, which serves as a substrate for the synthesis of the highly energetic 1,3,3-trinitroazetidine. 

Trinitroazetidine is an energetic material that is sensitive to detonation on impact <1995JOC1959>. 

J.C. Oxley, J.L. Smith, W. Zheng, E. Rogers, M.D. Cobum, Thermal Decomposition Pathways of 1,3,3-Trinitroazetidine (TNAZ), Related 3,3-Dinitrozetidinium Salts, and 15N, 13C, and 2H Isotopomers" J. Phys. Chem... 

P. Politzer J. M. Seminario, Energy Changes Associated With Some Decomposition Steps of 1,3,3-Trinitroazetidine. A Non-Local Density Functional Study, Chem. Phys. Letts, 207 (1993) 27-30. 

Fig. 1.7 Molecular structures of 5-nitro-l,2,4-triazol-3-one (NTO), 1,3,3-trinitroazetidine (TNAZ), hexanitrohexaazaisowurtzitane (CL-20), octanitrocubane (ONC) and 4,10-dinitro-2,6,8,12-tetraoxa-4,10-diazaisowurtzitane (TEX).

Axenrod, T., Watnick, C., and Yazdekhasti, H. 1995. Synthesis of 1,3,3-trinitroazetidine via the oxidative nitrolysis of A-p-tosyl-3-azetidinone oxime. Journal of Organic Chemistry, 60(7) 1959-64. 

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