Improvement of Thermal Stability and Sensitivity of Furazan/Furoxan via Ring Closure Generation of Vicinal Amino-Nitro Structure.
J Org Chem
; 89(7): 4444-4452, 2024 Apr 05.
Article
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| MEDLINE
| ID: mdl-38501594
ABSTRACT
Energetic compounds that display high thermal stability and insensitivity properties are essential for applications in mining, gas drilling, etc. In this work, a novel 4-nitro-5-aminoisoxazole energetic moiety oriented to enhance thermal stability and decrease the sensitivity of furazan/furoxan analogues was constructed. The generation of a vicinal amino-nitro structure can be effectively realized in one step by a green and mild ring-closing reaction of nitroacetonitrile potassium salt with chloroxime in aqueous solution. Seven new energetic compounds with good thermal stability (Td 155.8â¼270.3 °C) and low sensitivity (IS >40 J, FS 96â¼192 N) were synthesized. The nitro-furazan and isoxazole combined product exhibits the advantages of both skeletons, with energetic properties (Dv = 8350 m s-1, P = 30.1 GPa) that may find value in insensitive energetic materials. This strategy promises to achieve a balance between energy levels and stability of furazan/furoxan analogues and offers a new way for the design and synthesis of highly thermally stable compounds that meet special applications.
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MEDLINE
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J Org Chem
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2024
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Article