1,3,5-Triazido-2,4,6-trinitrobenzene

1,3,5-Triazido-2,4,6-trinitrobenzene, also known as TATNB (triazidotrinitrobenzene) and TNTAZB (trinitrotriazidobenzene), is an aromatic high explosive composed of a benzene ring with three azido groups (-N) and three nitro groups (-NO) alternating around the ring, giving the chemical formula C(N)(NO). Its velocity of detonation is 7,350 meters per second, comparable to TATB (triaminotrinitrobenzene).
Preparation.
The compound was first synthesized in 1924 by Oldřich Turek. It can be prepared by the reaction of 1,3,5--trichloro-2,4,6-trinitrobenzene with sodium azide, which is obtained from the nitration of 1,3,5-trichlorobenzene with nitric acid and sulfuric acid.
Another route uses the nitration of 1,3,5-triazido-2,4-dinitrobenzene.
Properties.
Physical properties.
1,3,5-Triazido-2,4,6-trinitrobenzene forms yellow crystalline solids that melt at 131 °C. The crystals are monoclinic with space group P21/c. Its formation is highly endothermic, with an enthalpy of formation of 765.8 kJ/mol and an enthalpy of combustion of 3200 kJ/mol.
Chemical Properties.
Even at low temperatures, the compound slowly decomposes by giving off nitrogen gas, converting into benzotrifuroxan. This reaction proceeds quantitatively within 14 hours at 100 °C. As a solution in m-xylene, first order kinetics were observed for the decomposition, with a half-life of 340 minutes at 70 °C, 89 minutes at 80 °C, and 900 seconds at 100 °C.
The compound explodes if rapidly heated above 168 °C.