Synthesis and characterization of 3,6-bis(1H-1,2,3,4-tetrazol-5-ylamino)-1,2,4,5-tetrazine (BTATz): Novel high-nitrogen content insensitive high energy material

Journal of Hazardous Materials

Volumn 170, Issue 1, 2009, Pages 306-313

  Saikia, A ^a   Sivabalan, R ^a   Polke, B G ^a   Gore, G M ^a   Singh, Amarjit ^a   Subhananda Rao, A ^a   Sikder, A K ^a  

^a HIGH ENERGY MATERIALS RESEARCH LABORATORY   (India)

Author keywords

Gas generant; High nitrogen content high energy materials (HNC HEMs); Insensitive ingredient; Synthesis; Tetrazine; Thermolysis

Indexed keywords

ENERGY OF ACTIVATION; HEAT OF EXPLOSION; HIGH-NITROGEN; HIGH-NITROGEN CONTENT HIGH ENERGY MATERIALS (HNC-HEMS); INSENSITIVE HIGH ENERGY MATERIALS; INSENSITIVE INGREDIENT; SPECTROSCOPIC TECHNIQUE; SYNTHESIS; SYNTHESIS AND CHARACTERIZATION; TETRAZINE; TGA AND DSC;

ACTIVATION ENERGY; NITROGEN; THERMOLYSIS;

SYNTHESIS (CHEMICAL);

3 (1H 1,2,3,4 TETRAZOL 5 YLAMINO) 6 (3,5 DIMETHYL PYRAZOL 1 YL)TETRAZINE; 3,6 BIS(1H 1,2,3,4 TETRAZOL 5 YLAMINO) 1,2,4,5 TETRAZINE; NITROGEN; TETRAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ACTIVATION ENERGY; ATOMIC ABSORPTION SPECTROSCOPY; BIOENERGETICS; CHEMOSYNTHESIS; EXPERIMENTAL STUDY; NITROGEN; THERMAL DECOMPOSITION;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CONTROLLED STUDY; DECOMPOSITION; EXPLOSION; HEAT; INFRARED SPECTROSCOPY; SCANNING ELECTRON MICROSCOPY; SYNTHESIS; TEMPERATURE;

EXPLOSIONS; EXPLOSIVE AGENTS; GASES; MOLECULAR STRUCTURE; TEMPERATURE; TETRAZOLES; THERMODYNAMICS;

EID: 67749127241     PISSN: 03043894     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jhazmat.2009.04.095     Document Type: Article

References (21)

1. Chavez D.E., Gilardi R.D., and Hiskey M.A. 3,3′-Azobis(6-amino-1,2,4,5-tetrazine): a novel high-nitrogen energetic material. Angew. Chem. Int. Ed. 39 (2000) 1791-1793
2. Chavez D.E., and Hiskey M.A. 1,2,4,5-Tetrazine based energetic materials. J. Energy Mater. 17 (1999) 357-377
3. Boger D.L., and Weinreb S.M. Hetero Diels-Alder Methodology in Organic Synthesis (1987), Academic Press, New York pp. 239-299
4. Panek J.S., and Zhu B. Synthesis of aromatic 1,2-diazines by inverse electron demand Diels-Alder reaction of polymer-supported 1,2,4,5-tetrazines. Tetrahedron Lett. 37 (1996) 8151-8154
5. Boger D.L., Coleman R.S., Panek J.S., and Yohannes D.J. Thermal cycloaddition of dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate with electron-rich olefins: 1,2-diazine and pyrrole introduction. Preparation of octamethylporphin (OMP). Org. Chem. 49 (1984) 4405-4409
6. Boger D.L., and Zhang M.J. Total synthesis of (±)-cis and (±)-trans-Trikentrin A: Diels-Alder reactions of heteroaromatic azadienes. J. Am. Chem. Soc. 113 (1991) 4230-4234
7. Audebert P., Sadki S., Miomandre F., Clavier G., Vernieres M.C., Saoud M., and Hapiot P. New functionalized tetrazines: synthesis, electrochemical and spectroscopic properties. New J. Chem. 28 (2004) 387-392
8. Novak Z., Bostai B., Csekei M., Lorincz K., and Kotschy A. Selective nucleofilic substitution on tetrazines. Heterocycles 60 (2003) 2653-2668
9. Farago J., Novak Z., Schlosser G., Csampai A., and Kotschy A. The azaphilic addition of organometallic reagents on tetrazines: scope and limitations. Tetrahedron 60 (2004) 1991-1996
10. Wilkes M.C. Azaphilic addition of methyl lithium to 3,6-bisalkylthio-1,2,4,5-tetrazines: a remarkable dochotomy. J. Heterocycl. Chem. 28 (1991) 1163-1164
11. Novak Z., and Kotschy A. The first cross-coupling reactions on tetrazines. Org. Lett. 5 (2003) 3495-3497
12. Glidewell C., Lightfoot P., Royles B.J.L., and Smith D.M.J. The inverse electron-demand Diels-Alder reaction in polymer synthesis. Part 4. The preparation and crystal structures of some bis(1,2,4,5-tetrazines). Chem. Soc., Perkin Trans. 2 (1997) 1167
13. Sakya S.M., Groskopf K.K., and Boger D.L. 3-Methoxy-6-methylthio-1,2,4,5-tetrazine. Tetrahedron Lett. 38 (1997) 3805-3808
14. Boger D.L., Schaum R.P., and Garbaccio R.M. Regioselective inverse electron demand Diels-Alder reactions of N-acyl 6-amino-3-methylthio-1,2,4,5-tetrazines. J. Org. Chem. 63 (1998) 6329-6337
15. Chavez D.E., Hiskey M.A., and Naud D.L. Tetrazine explosives. Propel. Explos. Pyrotech. 29 (2004) 209-215
16. Chavez D.E., Hiskey M.A., and Gilardi R.D. Novel high-nitrogen materials based on nitroguanyl substituted tetrazines. Org. Lett. 6 (2004) 2889-2891
17. Yue S.-T., and Yang S.-Q. Synthesis and characterization of 3,6-bis(1H-1,2,3,4-tetrazol-5-yl-amino)-1,2,4,5-tetrazine. Hecheng Huaxue 12 (2004) 164-166
18. Xu S.-L., Yang S.-Q., and Yue S.-T. Synthesis and research of 3,6-bis(1H-1,2,3,4-tetrazol-5-yl-amino)-1,2,4,5-tetrazine. Hanneng Cailiao 12 (2004) 44-47
19. Arvani L., and Hutchinson R. The sensitivity of impact and friction. Energetic Materials-Technology of the Inorganic Azide vol.2 (1977), Plenum Press, New York pp. 111-158
20. Muthurajan H., Sivabalan R., Talawar M.B., and Asthana S.N. Computer simulation for prediction of performance and thermodynamic parameters of high energy materials. J. Hazard. Mater. A112 (2004) 17-33
21. Muthurajan H., Sivabalan R., Talawar M.B., Venugopalan S., and Gandhe B.R. Computer code for the optimization of performance parameters of mixed explosive formulations. J. Hazard. Mater. 136 (2006) 475-481