DOI QR코드

DOI QR Code

Synthesis and Characterization of 5-Dinitromethyltetrazole

  • Lim, Choong-Hwan (High Energy Research Center, Department of Chemistry, Inha University) ;
  • Hong, Seong-Ho (High Energy Research Center, Department of Chemistry, Inha University) ;
  • Chung, Kyoo-Hyun (High Energy Research Center, Department of Chemistry, Inha University) ;
  • Kim, Jin-Seuk (Agency for Defense Developmen) ;
  • Cho, Jin-Rai (Agency for Defense Developmen)
  • Published : 2008.07.20

Abstract

Keywords

References

  1. Chung, K.-H.; Kil, H.-S.; Choi, I.; Chu, C.-K.; Lee, I.-M. J. Heterocyclic Chem. 2000, 37, 1651-1654 https://doi.org/10.1002/jhet.5570370641
  2. Zhang, M.-X.; Eaton, P. E.; Gilardi, R. Angew. Chem. Int. Ed. 2000, 39, 401 https://doi.org/10.1002/(SICI)1521-3773(20000117)39:2<401::AID-ANIE401>3.0.CO;2-P
  3. Oh, C. H.; Park, D. I.; Ryu, J. H.; Cho, J. H.; Han, J.-S. Bull. Korean Chem. Soc. 2007, 28, 322 https://doi.org/10.5012/bkcs.2007.28.2.322
  4. Latypov, N. V.; Bergman, J.; Langlet, A.; Wellmar, U.; Bemm, U. Tetrahedron 1998, 54, 11525 https://doi.org/10.1016/S0040-4020(98)00673-5
  5. Bellamy, A. J.; Latipov, N. V.; Goede, P. J. Chem. Research (S) 2002, 257
  6. Baum, K.; Bigelow, S. S.; Nguyen, N. V.; Archibald, T. G. J. Org. Chem. 1992, 57, 235 https://doi.org/10.1021/jo00027a042
  7. Einberg, F. J. Org. Chem. 1964, 29, 2021 https://doi.org/10.1021/jo01030a510
  8. Terpigorev, A. N.; Tselinskii, I. V.; Makarevich, A. V.; Frolova, G. M.; Mel'nikova, A. A. J. Org. Chem. USSR 1987, 23, 214
  9. Katritzky, A. R.; Sommen, G. L.; Gromova, A. V.; Witek, R. M.; Steel, P. J.; Damavarapu, R. Chem. Heterocycl. Comp. 2005, 41, 111 https://doi.org/10.1007/s10593-005-0116-5
  10. Butler, R. N. In Comprehensive Heterocyclic Chemistry, 1st ed; Potts, K. T., Ed.; Pergamon Press: Oxford, U. K., 1984; Vol. 5, p 791
  11. Saalfrank, R. W.; Fischer, M.; Wirth, U.; Zimmermann, H. Angew. Chem., Int. Ed. Engl. 1987, 26, 1160 https://doi.org/10.1002/anie.198711601
  12. Cai, H.; Shu, Y.; Huang, H.; Cheng, B.; Li, J. J. Org. Chem. 2004, 69, 4369 https://doi.org/10.1021/jo030395f
  13. Astrat'ev, A. A.; Dashko, D. V.; Mershin, A. Y.; Stepanov, A. I.; Urazgil'deev, N. A. J. Org. Chem. USSR 2001, 37, 729 https://doi.org/10.1023/A:1012568305472
  14. Holmgren, E.; Carlsson, H.; Goede, P.; Latypov, N.; Crescenzi, C. 34th Int. Ann. Conf. ICT; Karlsruhe: Germany, 2003; CAN 140:341678
  15. Wiberg, N.; Bayer, H.; Bachhuber, H. Angew. Chem. 1975, 87, 202 https://doi.org/10.1002/ange.19750870611
  16. Parker, C. O. Tetrahedron 1962, 17, 109 https://doi.org/10.1016/S0040-4020(01)99009-X
  17. Shchurova, N. A.; Tyrkov, A. G. J. Org. Chem. USSR 2006, 42, 1583
  18. Kalyamina, A. V.; Tyrkov, A. G. CAN 145:419029
  19. Tyrkov, A. G.; Paschenkko, K. P.; Ladyzhnikova, T. D.; Altukhov, K. V. CAN 145:419029
  20. Ladyzhnikova, T. D.; Tyrkov, A. G.; Altukhov, K. V.; Berkova, G. A. CAN 120:30721
  21. Ladyzhnikova, T. D.; Tyrkov, A. G.; Altukhov, K. V.; Pozdnyakov, V. P.; Dekaprolevich, M. O.; Rezchikova, K. I. CAN 118:212201
  22. Finnegan, W. G.; Henry, R. A.; Lofquist, R. J. Am. Chem. Soc. 1958, 80, 3908 https://doi.org/10.1021/ja01548a028
  23. Grakauskas, V.; Albert, A. H. J. Heterocyclic. Chem. 1981, 18, 1477 https://doi.org/10.1002/jhet.5570180741
  24. Linn, W. H. W.; Schoepp, D. D.; Calligaro, D. O.; Vasileff, R. T.; Heinz, L. J.; Salhoff, C. R.; O'Malley, P. J. J. Med. Chem. 1992, 35, 4608 https://doi.org/10.1021/jm00102a015
  25. Shastin, A. V.; Godovikova, T. I.; Korsunskii, B. L. Chem. Heterocycl. Comp. 1998, 34, 383 https://doi.org/10.1007/BF02290739
  26. Garver, L. C.; Grakaukas, V.; Baum, K. J. Org. Chem. 1985, 50, 1699 https://doi.org/10.1021/jo00210a600
  27. Kaplan, R. B.; Shechter, H. J. Am. Chem. Soc. 1961, 83, 3535 https://doi.org/10.1021/ja01477a047
  28. Archibald, T. G.; Gilard, R.; Baum, K. George, C. J. Org. Chem. 1990, 55, 2920 https://doi.org/10.1021/jo00296a066
  29. Marchand, A. P.; Rajagopal, D.; Bott, S. G.; Archibald, T. G. J. Org. Chem. 1995, 60, 4943 https://doi.org/10.1021/jo00120a049
  30. Katritzky, A. R.; Cundy, D. J.; Chen, J. J. Heterocyclic. Chem. 1994, 31, 271 https://doi.org/10.1002/jhet.5570310202
  31. Axenrod, T.; Watnick, C.; Yazdekhasti, H. J. Org. Chem. 1995, 60, 1959 https://doi.org/10.1021/jo00112a014
  32. Parker, C. O.; Emmons, W. D.; Rolewicz, H. A.; McCallum, K. S. Tetrahedron 1962, 17, 79 https://doi.org/10.1016/S0040-4020(01)99006-4
  33. Brown, J. F. J. Am. Chem. Soc. 1955, 77, 6341 https://doi.org/10.1021/ja01628a078
  34. Kim, N. J. Bull. Korean Chem. Soc. 2006, 27, 1009 https://doi.org/10.5012/bkcs.2006.27.7.1009

Cited by

  1. ChemInform Abstract: Synthesis and Characterization of 5-Dinitromethyltetrazole. vol.39, pp.45, 2008, https://doi.org/10.1002/chin.200845140
  2. Dinitromethyltetrazole and its Salts - A Comprehensive Study vol.35, pp.2, 2009, https://doi.org/10.1002/prep.200900049
  3. -1,2,4-triazole vol.133, pp.49, 2011, https://doi.org/10.1021/ja208990z
  4. Synthesis, Spectral Characterization, Crystal Structure and Thermal Behavior of Tert-butyl 2,2-bis(2,4-dinitrophenyl)ethanoate vol.42, pp.11, 2012, https://doi.org/10.1007/s10870-012-0363-0
  5. New Molecular Salts from Chloronitroaromatic Compounds, 1,3-Disubstituted pyrimidine-2,4,6(1H,3H,5H)-trione and Amines: Synthesis, Characterization, Thermal Behavior and Crystal Structure vol.44, pp.5, 2014, https://doi.org/10.1007/s10870-014-0507-5
  6. Tetrazoles as carboxylic acid isosteres: chemistry and biology vol.78, pp.1-4, 2014, https://doi.org/10.1007/s10847-013-0334-x
  7. Design and synthesis of energetic materials towards high density and positive oxygen balance by N-dinitromethyl functionalization of nitroazoles vol.4, pp.15, 2016, https://doi.org/10.1039/C6TA01501H
  8. New Energetic Polynitrotetrazoles vol.21, pp.9, 2015, https://doi.org/10.1002/chem.201405659
  9. Desensitization of the dinitromethyl group: molecular/crystalline factors that affect the sensitivities of energetic materials pp.2050-7496, 2018, https://doi.org/10.1039/C8TA09176E
  10. 4,5-Dihydro-1H-tetrazoles — 5-Alkyl/Aryl and 5-Alkylidene Derivatives vol.96, pp.4, 2018, https://doi.org/10.3987/REV-17-879
  11. Synthesis of 5-dinitromethyltetrazole vol.82, pp.10, 2009, https://doi.org/10.1134/S1070427209100103
  12. PI Index: A New Quantitative Scale for Screening Insensitive High Energy Density Materials vol.30, pp.5, 2008, https://doi.org/10.5012/bkcs.2009.30.5.1177
  13. Synthesis and Characterization of Some Polynitro Imidazoles vol.30, pp.9, 2009, https://doi.org/10.5012/bkcs.2009.30.9.2152
  14. Synthesis and Characterization of Bisnitrofurazanofuroxan vol.31, pp.5, 2008, https://doi.org/10.5012/bkcs.2010.31.5.1400
  15. New pyrazole energetic materials and their energetic salts: combining the dinitromethyl group with nitropyrazole vol.49, pp.5, 2008, https://doi.org/10.1039/c9dt04235k