Benzofuroxan (Benzo[1,2-c]1,2,5-oxadiazole N-oxide) Derivatives as Potential Energetic Materials: Studies on Their Synthesis and Properties

• Autorzy: Šarlauskas J. , Anusevičius Z. , Misiunas A.
• Języki publikacji: EN

Abstrakty

EN

The objective of this work was to prepare benzofuroxan derivatives as new, dense, potentially energetic materials and to investigate their properties, with the main focus being on 5,6-dinitrobenzofuroxan (5,6-DNBF). 5,6-DNBF was prepared by a 3-step reaction sequence: a) 1-azido-3-nitrobenzene was synthesized by diazotation of 3-nitroaniline with sodium nitrite and subsequent reaction with sodium azide in acetic/sulfuric mixed acids; b) it was nitrated with HNO3/H2SO4 to 1-azido-2,4,5-trinitrobenzene; c) thermal cyclization of the latter compound in a polar solvent gave the desired 5,6-DNBF (m.p. 177 °C). It was fully characterized by UV/VIS, FT-IR and NMR spectroscopy, mass spectrometry and single crystal X-ray diffraction. The density of the compound (X-ray) was found to be comparatively high (1.88 g/cm3), and to be superior to the previously known, isomeric energetic material ? 4,6-dinitrobenzofuroxan (4,6-DNBF) (1.76 g/cm3). Furthermore, the synthesis of some other benzofuroxan derivatives, potentially interesting as high energy, density materials (HEDMs), has been carried out. The densities of the compounds obtained were calculated using ACD Labs software (version 4.0). Based on the results obtained, it could be concluded that 5,6-DNBF is one of the densest nitro derivatives of the benzofuroxan series, comparable to CL-14, CL-17, CL-18, and thus could have potential applications as an HEDM.

Słowa kluczowe

EN

heterocyclic nitro compounds; X-ray diffraction; structure analysis; density; HEDM; 5,6-DNBF

• Czasopismo: Central European Journal of Energetic Materials
• Rocznik: 2012
• Tom: Vol. 9, nr 4
• Strony: 365--386
• Opis fizyczny: Bibliogr. 40 poz., fig.

Twórcy

autor

Šarlauskas J.

autor

Anusevičius Z.

autor

Misiunas A.

• Vilnius University, Institute of Biochemistry, Mokslinink? 12, LT-08662 Vilnius, Lithuania,

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