Development of Melt-Castable Explosive: Targeted Synthesis of 3,5-Dinitro-4-Methylnitramino-1-Methylpyrazole and Functional Derivatization of Key Intermediates
The problems associated with TNT necessitate the development of novel melt-castable compounds with melting points between 70 and 120 °C, a crucial endeavor in the field of energetic materials. This study introduces a promising melt-castable explosive based on nitropyrazole, whose melt-castable prope...
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MDPI AG
2025-06-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/30/13/2796 |
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| author | Elena Reinhardt Lukas Bauer Antonia H. Stadler Henrik R. Wilke Arthur Delage Jörg Stierstorfer Thomas M. Klapötke |
| author_facet | Elena Reinhardt Lukas Bauer Antonia H. Stadler Henrik R. Wilke Arthur Delage Jörg Stierstorfer Thomas M. Klapötke |
| author_sort | Elena Reinhardt |
| collection | DOAJ |
| description | The problems associated with TNT necessitate the development of novel melt-castable compounds with melting points between 70 and 120 °C, a crucial endeavor in the field of energetic materials. This study introduces a promising melt-castable explosive based on nitropyrazole, whose melt-castable properties were achieved by the introduction of methyl groups. The synthesis of 3,5-dinitro-4-methylnitramino-1-methylpyrazole involves a three-step process starting from 3,5-dinitro-4-chloropyrazole, including substitution, nitration, and methylation reactions. Additionally, two alternative synthesis routes and six energetic salts were examined. Structural elucidation was conducted using conventional methods such as NMR, IR, and X-ray, while the energetic properties of the compound, including thermal behavior, sensitivities, and theoretical performance, were investigated. Also, compatibility with common explosives was investigated, the experimental enthalpy of formation by bomb calorimetry was determined, and an SSRT test was performed. Furthermore, the melt-cast explosive underwent an Ames test in order to assess its toxicity. |
| format | Article |
| id | doaj-art-f2d94d8fbdd34c5287c96081af526c80 |
| institution | DOAJ |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-f2d94d8fbdd34c5287c96081af526c802025-08-20T03:16:42ZengMDPI AGMolecules1420-30492025-06-013013279610.3390/molecules30132796Development of Melt-Castable Explosive: Targeted Synthesis of 3,5-Dinitro-4-Methylnitramino-1-Methylpyrazole and Functional Derivatization of Key IntermediatesElena Reinhardt0Lukas Bauer1Antonia H. Stadler2Henrik R. Wilke3Arthur Delage4Jörg Stierstorfer5Thomas M. Klapötke6Department of Chemistry, Ludwig-Maximilians-University of Munich, Butenandtstr. 5–13, 81377 Munich, GermanyDepartment of Chemistry, Ludwig-Maximilians-University of Munich, Butenandtstr. 5–13, 81377 Munich, GermanyDepartment of Chemistry, Ludwig-Maximilians-University of Munich, Butenandtstr. 5–13, 81377 Munich, GermanyDepartment of Chemistry, Ludwig-Maximilians-University of Munich, Butenandtstr. 5–13, 81377 Munich, GermanyEurenco, 84700 Sorgues, FranceDepartment of Chemistry, Ludwig-Maximilians-University of Munich, Butenandtstr. 5–13, 81377 Munich, GermanyDepartment of Chemistry, Ludwig-Maximilians-University of Munich, Butenandtstr. 5–13, 81377 Munich, GermanyThe problems associated with TNT necessitate the development of novel melt-castable compounds with melting points between 70 and 120 °C, a crucial endeavor in the field of energetic materials. This study introduces a promising melt-castable explosive based on nitropyrazole, whose melt-castable properties were achieved by the introduction of methyl groups. The synthesis of 3,5-dinitro-4-methylnitramino-1-methylpyrazole involves a three-step process starting from 3,5-dinitro-4-chloropyrazole, including substitution, nitration, and methylation reactions. Additionally, two alternative synthesis routes and six energetic salts were examined. Structural elucidation was conducted using conventional methods such as NMR, IR, and X-ray, while the energetic properties of the compound, including thermal behavior, sensitivities, and theoretical performance, were investigated. Also, compatibility with common explosives was investigated, the experimental enthalpy of formation by bomb calorimetry was determined, and an SSRT test was performed. Furthermore, the melt-cast explosive underwent an Ames test in order to assess its toxicity.https://www.mdpi.com/1420-3049/30/13/2796melt-castable explosivespyrazolecompatibilitybomb calorimetrySSRTtoxicity |
| spellingShingle | Elena Reinhardt Lukas Bauer Antonia H. Stadler Henrik R. Wilke Arthur Delage Jörg Stierstorfer Thomas M. Klapötke Development of Melt-Castable Explosive: Targeted Synthesis of 3,5-Dinitro-4-Methylnitramino-1-Methylpyrazole and Functional Derivatization of Key Intermediates Molecules melt-castable explosives pyrazole compatibility bomb calorimetry SSRT toxicity |
| title | Development of Melt-Castable Explosive: Targeted Synthesis of 3,5-Dinitro-4-Methylnitramino-1-Methylpyrazole and Functional Derivatization of Key Intermediates |
| title_full | Development of Melt-Castable Explosive: Targeted Synthesis of 3,5-Dinitro-4-Methylnitramino-1-Methylpyrazole and Functional Derivatization of Key Intermediates |
| title_fullStr | Development of Melt-Castable Explosive: Targeted Synthesis of 3,5-Dinitro-4-Methylnitramino-1-Methylpyrazole and Functional Derivatization of Key Intermediates |
| title_full_unstemmed | Development of Melt-Castable Explosive: Targeted Synthesis of 3,5-Dinitro-4-Methylnitramino-1-Methylpyrazole and Functional Derivatization of Key Intermediates |
| title_short | Development of Melt-Castable Explosive: Targeted Synthesis of 3,5-Dinitro-4-Methylnitramino-1-Methylpyrazole and Functional Derivatization of Key Intermediates |
| title_sort | development of melt castable explosive targeted synthesis of 3 5 dinitro 4 methylnitramino 1 methylpyrazole and functional derivatization of key intermediates |
| topic | melt-castable explosives pyrazole compatibility bomb calorimetry SSRT toxicity |
| url | https://www.mdpi.com/1420-3049/30/13/2796 |
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