Benzotrifuroxan

Benzotrifuroxan is a heterocyclic organic compound that is related to 1,2,5-oxadioles. The high-energy compound is explosive.

History

The compound was first synthesized in 1924 by O. Turek as hexanitrosobenzene. In addition to the hexanitroso structure, symmetric polycyclic structures could also be formulated.

Characteristics

Physical properties

Benzotrifuroxan is a crystalline solid that melts at 195 °C.  The compound crystallizes in an orthorhombic crystal lattice with the space group Pna2₁.  The molar enthalpy of formation is 606 kJ·mol^{−1}, the enthalpy of combustion is −2967 kJ·mol^{−1}.

Chemical properties

Benzotrifuroxan can decompose explosively. The heat of explosion is 5903 kJ·kg ^{−1}, the detonation speed is 8.61 km·s ^{−1}.  The compound is sensitive to impact.

Benzotrifuroxan forms stable complexes with aromatic hydrocarbons such as naphthalene, 1-phenylnaphthalene, 2-phenylnaphthalene and tetrahydronaphthalene. Recrystallization in benzene yields a 1:1 complex with the solvent, whereby the benzene can only be removed at 100 °C in vacuum.

Synthesis

Benzotrifuroxan can be obtained by thermal degradation of 1,3,5-triazido-2,4,6-trinitrobenzene.

A further synthesis can be carried out by reacting 5,7-dichloro-4,6-dinitronbenzofuroxan with sodium azide.

Uses

In combination with TNT, the compound can be used to produce nanodiamonds using detonation shock waves.

References

attribution translated from the German article