Synthesis and Characterization of N 3-(2,2,2-Trinitroethyl)-1,2,4-Oxadiazole-3,5-Diamine

The reaction of 1,2,4-oxadiazole-3,5-diamine with 2-fluoro-2,2-dinitroethanol or 2,2,2-trinitroethanol was studied. Only the 3-amino group was found to be reactive and underwent efficient Mannich-type condensation with 2,2,2-trinitroethanol, while only trace amounts of product from condensation with 2-fluoro-2,2-dinitroethanol were formed. N 3-(2,2,2-Trinitroethyl)-1,2,4-oxadiazole-3,5-diamine was fully characterized, and its crystal structure and explosive sensitivity properties were determined. Calculated performance properties show that the product is a promising RDX-like material with a higher oxidizing potential.

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References

  1. 1.

    (a) Fischer, N.; Klapӧtke, T. M.; Stierstorfer, J. New Trends in Research of Energetic Materials, Proceedings of the 15th Seminar, Pardubice, Czech Republic, April 18–20, 2012; Pardubice, 2012, p. 130. (b) Chavez, D. E.; Klapӧtke, T. M.; Parrish, D.; Piercey, D. G.; Stierstorfer, J. Propellants, Explos., Pyrotech. 2014, 39, 641. (c) Klapӧtke, T. M.; Gӧbel, M.; Stierstorfer, J. Int. J. Energ. Mater. Chem. Propul. 2011, 10, 45. (d) He, C.; Shreeve, J. M. Angew. Chem. 2015, 127, 6358. (e) Klapӧtke, T. M.; Leroux, M.; Schmid, P. C.; Stierstorfer, J. Chem.–Asian. J. 2016, 11, 844. (f) Yin, P.; Zhang, J.; Parrish, D. A.; Shreeve, J. M. Chem.–Eur. J. 2014, 20, 16529. (g) Sheremetev, A. B.; Aleksandrova, N. S.; Palysaeva, N. V.; Struchkova, M. I.; Tartakovsky, V. A.; Suponitsky, K. Yu. Chem.–Eur. J. 2013, 19, 12446.

  2. 2.

    (a) Parker, G. A.; Reddy, G.; Major, M. A. Int. J. Toxicol. 2006, 25, 373. (b) Meyer, R.; Köhler, J.; Homburg, A. Explosives; Wiley-VCH: Weinheim, 2002, 5th ed., p. 253.

  3. 3.

    Dobratz, B. M. Lawrence Livermore National Laboratory Explosives Handbook; UCRL-52997: Livermore, 1985.

  4. 4.

    (a) Yin, P.; Zhang, Q.; Parrish, D. A.; Shreeve, J. M. J. Mater. Chem. A 2013, 1, 7500. (b) Li, S.; Zhang, W.; Wang, Y.; Zhao, X.; Zhang, L.; Pang, S. J. Energ. Mater. 2014, 32, S33. (c) Ovchinnikov, I. V.; Kulikov, A. S.; Epishina, M. A.; Makhova, N. N.; Tartakovsky, V. A. Russ. Chem. Bull., Int. Ed. 2005, 54, 1346. [Izv. Akad. Nauk., Ser. Khim. 2005, 1306.] (d) Epishina, M. A.; Finogenov, A. O.; Kulikov, A. S.; Makhova, N. N.; Anan'ev, I. V.; Tartakovsky, V. A. Rus. Chem. Bull., Int. Ed. 2012, 61, 1575. [Izv. Akad. Nauk., Ser. Khim. 2012, 1559.] (e) Yin, P.; Zhang, J.; He, C.; Parrish, D. A.; Shreeve, J. M. J. Mater. Chem. A 2014, 2, 3200. (f) DeHope, A.; Pagoria, P. F.; Parrish, D. A. LLNL-CONf-624954; Livermore National Laboratory: Livermore, 2013. (g) Yu, Q.; Yang, H.; Ju, X.; Lu, C.; Cheng, G. ChemistrySelect 2017, 2, 688.

  5. 5.

    (a) Thottempudi, V.; Zhang, J.; He, C.; Shreeve, J. M. RSC Adv. 2014, 4, 50361. (b) Tang, Y.; Gao, H.; Mitchell, L. A.; Parrish, D. A.; Shreeve, J. M. Angew. Chem., Int. Ed. 2016, 55, 1147.

  6. 6.

    Roemer, J. J.; Kaiser, D. W. US Patent 2648669.

  7. 7.

    Paine, R. T.; Koestle, W.; Borek, T.T.; Wood, G. L.; Pruss, E. A.; Duesler, E. N.; Hiskey, M. A. Inorg. Chem. 1999, 38, 3738.

    CAS  Article  Google Scholar 

  8. 8.

    (a) Byrd, E. F. C.; Rice, B. M. J. Phys. Chem. A 2006, 110, 1005. (b) Byrd, E. F. C.; Rice, B. M. J. Phys. Chem. A 2009, 113, 5813.

  9. 9.

    Fried, L. A.; Howard, W. M.; Bastea, S.; Glaesmann, K.; Souers, P. C.; Vitello, A.; Kuo, L. F. Cheetah Thermochemical Code; Lawrence Livermore National Laboratory: Livermore.

  10. 10.

    APEX3 v2015.5-2; Bruker AXS Inc.: Madison, 2015.

  11. 11.

    SAINT v8.34A; Bruker AXS Inc.: Madison, 2013.

  12. 12.

    XPREP v2014/2; Bruker AXS Inc.: Madison, 2014.

  13. 13.

    SADABS v2014/5; Bruker AXS Inc.: Madison, 2014.

  14. 14.

    Sheldrick, G. M. SHELXL-2014/7; University of Göttingen, 2014.

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Correspondence to David E. Chavez.

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Russian translation is published in Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(6/7), 737–739

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Chavez, D.E., Schulze, M.C. & Parrish, D.A. Synthesis and Characterization of N 3-(2,2,2-Trinitroethyl)-1,2,4-Oxadiazole-3,5-Diamine. Chem Heterocycl Comp 53, 737–739 (2017). https://doi.org/10.1007/s10593-017-2119-4

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Keywords

  • 2-fluoro-2,2-dinitroethanol
  • 1,2,4-oxadiazole
  • 2,2,2-trinitroethanol
  • energetic materials
  • Mannich reaction