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

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1,3,5-Triazido-2,4,6-trinitrobenzene
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Abbreviations TATNB
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MeSH C043826
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Template:Longitem Template:Chembox Elements/molecular formula
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Appearance yellow crystals[1]
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Template:Longitem monoclinic
Template:Longitem P21/c, No. 14
Template:Longitem 765.8 kJ/mol
Template:Longitem 3200 kJ/mol
Detonation velocity 7350 m/s

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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).

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

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