Citation: Wang Qi, Wang Chen-Bin, Pang Fu-Qing, Lu Tian, Yin Hong-Quan, Chen Fu-Xue. Synthesis and characterization of functionalized 1, 3-bis(2-alkyltetrazol-5-yl)triazenes[J]. Chinese Chemical Letters, ;2017, 28(8): 1784-1787. doi: 10.1016/j.cclet.2017.04.006 shu

Synthesis and characterization of functionalized 1, 3-bis(2-alkyltetrazol-5-yl)triazenes

School of Chemistry & Chemical Engineering, Beijing Institute of Technology, Beijing 100081, China

Corresponding author: Chen Fu-Xue, fuxue.chen@bit.edu.cn
Received Date: 19 January 2017
Revised Date: 6 April 2017
Accepted Date: 7 April 2017
Available Online: 18 August 2017

Figures(3)

A series of 1, 3-bis(2-alkyltetrazol-5-yl)triazenes have been synthesized in high yields by treatment of sodium nitrite and hydrochloric acid with substituted-5-aminotetrazoles. All compounds were fully characterized using IR spectroscopy, ¹H NMR and ¹³C NMR spectroscopy and high resolution mass spectrometer (HRMS). Most of these triazenes exhibit good detonation performance comparable with TNT and low melting points ranging from 81 ℃ to 106 ℃, which are suitable for melt-cast explosives. Among these compounds, 1, 3-bis(2-azidoethyltetrazol-5-yl)triazene (2g) displays a low melting point (106 ℃), moderate onset decomposition temperature (183 ℃) and good detonation performance (D: 7087 m/s; P: 17.6 GPa).
- Melt-cast explosives,
- Tetrazoles,
- Bis(tetrazolyl)triazenes,
- Nitrogen-rich compounds,
- Detonation parameter
1. [1]
  Agrawal J.P., Hodgson R.D.. Organic Chemistry of Explosives, John Wiley & Sons[J]. Chichester, 2007.
2. [2]
  Ravi P., Badgujar D.M., Gore G.M., Tewari S.P., Sikder A.K.. Review on melt cast explosives[J]. Propellants Explos. Pyrotech., 2011,36:393-403. doi: 10.1002/prep.201100047
3. [3]
  Pagoria P.F., Lee J.S., Mitchell A.R., Schmidt R.D.. A review of energetic materials synthesis[J]. Thermochim. Acta, 2002,384:187-204. doi: 10.1016/S0040-6031(01)00805-X
4. [4]
  (a) G. Zhang, M. Huang, Developmental discussion for insensitive high explosives with low melt point, Chin. J. Energy Mater. 23(2015) 103-105;
  (b) Y. N. Li, B. Z. Wang, Y. J. Shu, et al. , Synthesis and properties of potassium 5, 50-azobis(1-nitraminotetrazolate): a green primary explosive with superior initiation power, Chin. Chem. Lett. 28(2017) 117-120.
5. [5]
  Bonmassar L., Marchesi F., Pascale E.. Triazene compounds in the treatment of acute myeloid leukemia:a short review and a case report[J]. Curr. Med. Chem., 2013,20:2389-2401. doi: 10.2174/0929867311320190001
6. [6]
  Bräse S.. The virtue of the multifunctional triazene linkers in the efficient solidphase synthesis of heterocycle libraries[J]. Acc. Chem. Res., 2004,37:805-816. doi: 10.1021/ar0200145
7. [7]
  Nicolaou K.C., Boddy C.N.C., Bräse S., Winssinger N.. Chemistry, biology, and medicine of the glycopeptide antibiotics[J]. Angew. Chem. Int. Ed., 1999,38:2096-2152. doi: 10.1002/(ISSN)1521-3773
8. [8]
  (a) Q. Zhang, J. M. Shreeve, Growing catenated nitrogen atom chains, Angew. Chem. Int. Ed. 52(2013) 8792-8794;
  (b) Q. Wang, F. Pang, G. Wang, et al. , Pentazadiene: a high-nitrogen linkage in energetic materials, Chem. Commun. 53(2017) 2327-2330.
9. [9]
  (a) A. B. Sheremetev, N. S. Aleksandrova, T. M. Melnikova, et al. , Synthesis of difurazanyl ethers from 4, 4'-dinitroazoxyfurazan, Heteroatom Chem. 11(2000) 48-56;
  (b) T. M. Mel'nikova, T. S. Novikova, L. I. Khmel'nitskii, A. B. Sheremetev, Novel synthesis of 3, 4-dicyanofuroxan, Mendeleev Commun. 11(2001) 30-31;
  (c) A. B. Sheremetev, V. G. Andrianov, E. V. Mantseva, et al. , Synthesis of secondary and tertiary aminofurazans, Russ. Chem. Bull. Int. Ed. 53(2004) 596-614.
10. [10]
  (a) J. Reilly, J. Teegan, M. Carey, Coupling of diazonium complexes from an aliphatic base, Nature 159(1947) 643-644;
  (b) V. P. Shchipanov, A. I. Zabolotskaya, R. A. Badryzlova, Tetrazole derivatives. XⅡ. Synthesis and certain properties of 5-tetrazolylhydrazones, Chem. Heterocycl. Compd. 6(1975) 850.
11. [11]
  (a) K. Hattori, E. Lieber, J. P. Horwitz, The methylation of 5-hydroxytetrazole, J. Am. Chem. Soc. 78(1956) 411;
  (b) R. N. Butler, F. L. Scott, Synthesis of arylidene-2-methyl-2H-tetrazol-5-ylhydrazones via 1, 3-bis(2-methyl-2H-tetrazol-5-yl)triazene, J. Org. Chem. 32(1224) (1967);
  (c) P. J. Eulgem, A. Klein, N. Maggiarosa, D. Naumann, R. W. H. Pohl, New rare earth metal complexes with nitrogen-rich ligands: 5, 5'-bitetrazolate and 1, 3-bis(tetrazol-5-yl)triazenate-on the borderline between coordination and the formation of salt-like compounds, Chem. Eur. J. 14(2008) 3727-3736;
  (d) Q. Wang, H. Lu, F. Pang, et al. , Nitrogen-rich hypergolic ionic salts based on (2-methyltetrazol-5-yl)diazotates, RSC Adv. 6(2016) 56827-56830.
12. [12]
  Klapötke T.M., Minar N.K., Stierstorfer J.. Investigations of bis(methyltetrazolyl) triazenes as nitrogen-rich ingredients in solid rocket propellants-synthesis, characterization and properties[J]. Polyhedron, 2009,28:13-26. doi: 10.1016/j.poly.2008.09.015
13. [13]
  Lippert T., Wokaun A., Dautht J., Nuyken O.. NMR studies of hindered rotation and thermal decomposition of novel l-aryl-3, 3-dialkyltriazenes[J]. Magn. Reson. Chem., 1992,30:1178-1185. doi: 10.1002/(ISSN)1097-458X
14. [14]
  Frisch M.J., Trucks G.W., Schlegel H.B.. Gaussian 09, Revision E.01, Gaussian[J]. Inc., Wallingford, CT, 2009.
15. [15]
  H. H. Klause, Energetic Materials, in: U. Teipel (Ed. ), VCH, Weinheim, 2005.
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