3-picrylamino-l,2,4-triazole

B. Chen, J. Li and Y. On, Modified Preparation and Nitration of 3-Picrylamino-l,2,4-triazole , in Proc. 17th International Pyrotechnics Seminar (Combined with 2nd Beijing International Symposium on Pyrotechnics and Explosives), Beijing Institute Technical Press, Beijing, China, 196 (1991). 

Cl 4HgNi oOl 2 mw 506.30 N 27.67% OB to CO2 —60.04% cryst mp 260° (decompn) d 1.80g/cc sol in hot acet-ethanol mixt Prepn. Picryl fluoride (2.3 Ig, 0.01 mole) is added to a soln of 3-picrylamino-l,2,4-triazole (2.95g, 0.01 mole) and triethylamine (1.4ml, 0.01 mole) in 50ml of dimethylsulfoxide. The resulting soln is heated at 70° for 5 hrs, then poured into 400ml of ice and w. The mixt is then acidified with coned HCl and the solid collected by filtration, wadied with w, and dried. The material is recrystd twice from acet-ethanol to provide 3.78g (75% yield) of the product The compd has a 50% pt impact sensy of >320cm (TNT 160cm) using a LASL type 12 app (2.5-kg wt, sample on sandpaper) and exhibits a DTA exotherm at 150°... 

Amino-1,2,4-triazole is a useful starting material for the synthesis of many 1,2,4-triazole-based explosives. Jackson and Coburn synthesized a number of picryl- and picrylamino-substituted 1,2,4-triazoles. PATO (99) is synthesized from the reaction of 3-amino-1,2,4-triazole (98) with picryl chloride (67). ° PATO has also been synthesized from the reaction of 3-amino-l,2,4-triazole with A,2,4,6-tetranitromethylaniline (tetryl). PATO has a low sensitivity to impact and is thermally stable up to 310 °C. PATO (VOD 7469 m/s) exhibits lower performance to TATB (VOD 8000 m/s) which is the common benchmark standard for thermal stability and insensitivity in explosives. 

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