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 detonation velocity is 7,350 meters per second, which is comparable to TATB (triaminotrinitrobenzene).

1,3,5-Triazido-2,4,6-trinitrobenzene
Skeletal formula of TATNB
Space-filling model of the TATNB molecule
Names
Preferred IUPAC name
1,3,5-Triazido-2,4,6-trinitrobenzene
Identifiers
3D model (JSmol)
Abbreviations TATNB
ChemSpider
MeSH C043826
UNII
  • 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 checkY
    Key: LIPDUIOSIFXENT-UHFFFAOYSA-N checkY
  • 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
  • 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
C6N12O6
Molar mass 336.144 g·mol−1
Appearance yellow crystals[1]
Melting point 131 °C[2]
Structure[1]
monoclinic
P21/c, No. 14
Thermochemistry[1]
765.8 kJ/mol
3200 kJ/mol
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.[3] It can be prepared by the reaction of 1,3,5-trichloro-2,4,6-trinitrobenzene with sodium azide. 1,3,5-trichloro-2,4,6-trinitrobenzene is obtained from the nitration of 1,3,5-trichlorobenzene with nitric acid and sulfuric acid.[3]

Synthesis of 1,3,5-triazido-2,4,6-trinitrobenzene from 1,3,5-trichlorobenzene

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

Properties

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.[3] 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]

Decomposition of 1,3,5-triazido-2,4,6-trinitrobenzene

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): 7–11. doi:10.1002/1521-4087(200203)27:1<7::AID-PREP7>3.0.CO;2-J.
  2. 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. doi:10.1007/BF02495284. S2CID 95970971.
  3. Matyáš, Robert; Pachman, Jiří (2013). Primary Explosives. Springer Science & Business Media. pp. 118–121. ISBN 9783642284366.
  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.
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