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 (-N₃) and three nitro groups (-NO₂) alternating around the ring, giving the chemical formula C₆(N₃)₃(NO₂)₃. Its velocity of detonation is 7,350 meters per second, comparable to TATB (triaminotrinitrobenzene).

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

Names
IUPAC name 1,3,5-Triazido-2,4,6-trinitrobenzene
Identifiers
CAS Number	29306-57-8^Y
3D model (JSmol)	Interactive image Interactive image
ChemSpider	56578^Y
UNII	25NHL6Y97G^Y
CompTox Dashboard (EPA)	DTXSID30183552
InChI InChI=1S/C6N12O6/c7-13-10-1-4(16(19)20)2(11-14-8)6(18(23)24)3(12-15-9)5(1)17(21)22^Y Key: LIPDUIOSIFXENT-UHFFFAOYSA-N^Y InChI=1/C6N12O6/c7-13-10-1-4(16(19)20)2(11-14-8)6(18(23)24)3(12-15-9)5(1)17(21)22 Key: LIPDUIOSIFXENT-UHFFFAOYAO
SMILES O=[N+](c1c(N=[N+]=[N-])c([N+]([O-])=O)c(N=[N+]=[N-])c([N+]([O-])=O)c1N=[N+]=[N-])[O-] c1(c(c(c(c(c1[N+](=O)[O-])N=[N+]=[N-])[N+](=O)[O-])N=[N+]=[N-])[N+](=O)[O-])N=[N+]=[N-]
Properties
Chemical formula	C6N12O6
Molar mass	336.144 g·mol^−1
Appearance	yellow crystals[1]
Structure[1]
Crystal structure	monoclinic
Space group	P21/c, No. 14
Explosive data
Detonation velocity	7350 m/s
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Preparation

The compound was first synthesized in 1924 by Oldřich Turek.[2] 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.[2]

Another route uses the nitration of 1,3,5-triazido-2,4-dinitrobenzene.[1]

Properties

Physical properties

1,3,5-Triazido-2,4,6-trinitrobenzene forms yellow crystalline solids that melt at 131 °C.[3] 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.[1]

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.[2] 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.[4]

The compound explodes if rapidly heated above 168 °C.[1]

References

1. Adam, David; Karaghiosoff, Konstantin; Klapötke, Thomas M.; Holl, Gerhard; Kaiser, Manfred (2002). "Triazidotrinitro Benzene: 1,3,5‐(N₃)₃‐2,4,6‐(NO₂)₃C₆". Propellants Explos. Pyrotech. 27 (1). doi:10.1002/1521-4087%28200203%2927%3A1<7%3A%3AAID-PREP7>3.0.CO%3B2-J.
2. Matyáš, Robert; Pachman, Jiří (2013). Primary Explosives. Springer Science & Business Media. pp. 118–121. ISBN 9783642284366.
3. Burov, Yu. M.; Nazin, G. M.; Manelis, G. B. (1999). "Retardation of Monomolecular Reactions in the Solid Phase". Russian Chemical Bulletin. 48 (7): 1250–1254.
4. Korsunskii, B. L.; Apina, T. A. (1971). "Kinetics of the Thermal Decomposition of 1,3,5-Triazido-2,4,6-trinitrobenzene in Solution". Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science. 20 (9): 1971–1973. doi:10.1007/BF00854439.