Safer and Convenient Synthesis of 3,4-Bis(4-nitro-1,2,5-oxadiazol-3-yl)-1,2,5-oxadiazole-2-oxide (BNFF/DNTF),Organic Process Research & Development

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Safer and Convenient Synthesis of 3,4-Bis(4-nitro-1,2,5-oxadiazol-3-yl)-1,2,5-oxadiazole-2-oxide (BNFF/DNTF)
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2022-12-19 , DOI: 10.1021/acs.oprd.2c00250
Yuangang Xu ₁ , Shuaiqi Wang ₁ , Dongxue Li ₂ , Pengcheng Wang ₁ , Qiuhan Lin ₁ , Ming Lu ₁

Affiliation

A safer, convenient, and scalable synthesis for 3,4-bis(4-nitro-1,2,5-oxadiazol-3-yl)-1,2,5-oxadiazole-2-oxide (BNFF or DNTF) is described. The obtained products were fully characterized and further confirmed by single-crystal X-ray diffraction. The reaction process of tandem nitration–cyclization was optimized, and the thermal stability of the optimal reaction system was studied. 3-Amino-4-(carboxymethyl)furazan is oxidized and then treated with dilute mixed acid (HNO₃ and H₂SO₄) to obtain BNFF in a yield of 52% and a purity of 99% after liquid chromatography analysis. Compared with some previously reported multistep methods that relied on high-concentration hydrogen peroxide solutions and suffered from dangerous exothermic profiles, this new method used to synthesize BNFF promises to be safer and more efficient.

中文翻译：

更安全、更方便地合成 3,4-双(4-硝基-1,2,5-恶二唑-3-基)-1,2,5-恶二唑-2-氧化物 (BNFF/DNTF)

描述了 3,4-双（4-硝基-1,2,5-恶二唑-3-基）-1,2,5-恶二唑-2-氧化物（BNFF 或 DNTF）的更安全、方便和可扩展的合成. 通过单晶 X 射线衍射对所得产物进行了充分表征和进一步证实。对串联硝化-环化反应过程进行了优化，并对最优反应体系的热稳定性进行了研究。将 3-Amino-4-(carboxymethyl)furazan 氧化，然后用稀混合酸（HNO ₃和 H ₂ SO ₄)得到BNFF，收率52%，液相色谱分析纯度99%。与之前报道的一些依赖高浓度过氧化氢溶液并存在危险的放热曲线的多步方法相比，这种用于合成 BNFF 的新方法有望更安全、更高效。

更新日期：2022-12-19

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