2,5-dinitrobiguanidine | 53144-65-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,5-dinitrobiguanidine
• 英文别名: N'¹,N'²-dinitrohydrazine-1,2-bis(carboximidamide)；hydrazobisnitroformamidine；1-[(E)-[amino(nitramido)methylidene]amino]-2-nitroguanidine
• CAS: 53144-65-3
• 化学式: C₂H₆N₈O₄
• 分子量: 206.121
• InChiKey: ISPSBQXQZGJSDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  193
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,5-dinitrobiguanidine 在 溴 作用下， 以 水 为溶剂， 反应 0.25h， 以89%的产率得到N'¹,N'²-dinitrodiazene-1,2-bis(carboximidamide)
  参考文献：
  名称：

  2-Nitroguanidine Derivatives: VI. Synthesis and Chemical Properties of Hydrazo- and Azobis(nitroformamidine)

  摘要：

  New methods have been proposed for the synthesis of hydrazobis(nitroforynamidine), and its reactions with electrophilic reagents, formaldehyde and glyoxal, have been studied. Oxidation of hydrazobis(nitroformamidine) with atmospheric oxygen in glacial acetic acid in the presence of a catalytic amount of N2O4 gives crystalline azobis(nitroformamidine). Ionization constants of the oxidation product, determined by potentiometric titration (pK(a)(1) = 3.50, pK(a)(2) = 7.93), indicate considerable increase in the NH acidity as compared to 2-nitroguanidine. Reactions of azobis(nitroformamidine) with P-dicarbonyl compounds lead to formation of 1-diacylmethyl-N'(1),N'(2)-dinitrohydrazine-1,2-dicarboximidamides.

  DOI：

  10.1023/b:rujo.0000045193.49958.c4
• 作为产物：
  描述：

  N'¹,N'²-dinitrohydrazine-1,2-bis(carboximidamide) bis(aminoguanidinium) salt 在 硝酸 作用下， 以 水 为溶剂， 反应 0.67h， 以91%的产率得到2,5-dinitrobiguanidine
  参考文献：
  名称：

  2-Nitroguanidine Derivatives: VI. Synthesis and Chemical Properties of Hydrazo- and Azobis(nitroformamidine)

  摘要：

  New methods have been proposed for the synthesis of hydrazobis(nitroforynamidine), and its reactions with electrophilic reagents, formaldehyde and glyoxal, have been studied. Oxidation of hydrazobis(nitroformamidine) with atmospheric oxygen in glacial acetic acid in the presence of a catalytic amount of N2O4 gives crystalline azobis(nitroformamidine). Ionization constants of the oxidation product, determined by potentiometric titration (pK(a)(1) = 3.50, pK(a)(2) = 7.93), indicate considerable increase in the NH acidity as compared to 2-nitroguanidine. Reactions of azobis(nitroformamidine) with P-dicarbonyl compounds lead to formation of 1-diacylmethyl-N'(1),N'(2)-dinitrohydrazine-1,2-dicarboximidamides.

  DOI：

  10.1023/b:rujo.0000045193.49958.c4

文献信息

• Trailblazing 3D MOFs Featuring 1,2,4‐Dinitrimino Triazole: Redefining Energetic Materials and Iodine Encapsulation
  作者：Manojkumar Jujam、Richa Rajak、Srinivas Dharavath

  DOI：10.1002/adfm.202412638

  日期：2025.1

  The quest for high-performance energetic materials for defense and aerospace has intensified, focusing on balancing energy output and safety. This study presents the synthesis of 3D energetic metal-organic frameworks (EMOFs) [Na3(DNT)(H2O)]n (Na-MOF), [K2(DNT)2(H2O)]n (K-MOF), and [Cs2(DNT)]n (Cs-MOF) using 1,2,4-dinitrimino triazole (DNT) through a hydrothermal process. The synthesized EMOFs are characterized

  国防和航空航天领域对高性能含能材料的追求日益激烈，重点是平衡能源输出和安全性。本研究介绍了使用 1,2,4-二硝基三唑 （DNT） 通过水热工艺合成 3D 含能金属有机框架 （EMOF） [Na3（DNT）（H2O）]n （Na-MOF）、[K2（DNT）2（ ）]n （K-MOF） 和 [Cs2（DNT）]n （Cs-MOF）。使用红外光谱、粉末 X 射线衍射、扫描电子显微镜 （SEM）、元素分析、热重分析和差示扫描量热法对合成的 EMOFs 进行表征，并通过单晶 X 射线衍射确认结构，揭示了晶体密度分别为 2.15、2.16 和 2.86 g cm-3 的 3D 框架。其中，Na-MOF 表现出优异的爆震性能 （VOD = 8900 m s−1， DP = 26.21 GPa）、高热稳定性 （Td = 369 °C） 以及对冲击和摩擦不敏感 （IS = 40 J， FS = 360
• ——
  作者：A. A. Astrat'yev、D. V. Dashko、L. L. Kuznetsov

  DOI：10.1023/a:1026003700547

  日期：——

  1,2-Dinitroguanidine is a product of nitroguanidine nitration with nitric acid and its mixtures with sulfuric acid and oleum. It is a diacid (pK(a), 1.11, similar to 11.5) and at the same time a weak base undergoing protonation at the nitrogen of the amino group (pK(BH) + -5.81). The decomposition kinetics of 1,2-dinitro-guanidine was studied by spectrophotometric method both in acid and alkaline media, and the mechanism of the process was assumed. In the media of high acidity (H-o > -8) the 1,2-dinitroguanidine suffers reversible denitration into nitroguanidine. At lower acidity its conjugate acid or molecular form undergoes hydrolysis yielding nitrourea. Monoanion of 1,2-dinitroguanidine in a weak acid or in an alkali is hydrolyzed into N,N'-dinitrourea. The reaction of 1,2-dinitroguanidine with alkali in alcohol provides its salts, with nitrogen-containing bases form both salts and derivatives of 2-nitroguanidine. The treatment of 1,2-dinitroguanidine with haloalkanes results in its N-alkylated products.
• The Hydrazinolysis of Nitroguanidine in Alcoholic Systems. Preparation and Reactions of 1,6-Dinitrobiguanidine^1a,b
  作者：Ronald A. Henry、Sol Skolnik、G. B. L. Smith

  DOI：10.1021/ja01100a055

  日期：1953.2
• 2-Nitroguanidine Derivatives: V. Synthesis and Structure of 3,5-Bis(nitroamino)-1,2,4-triazole Salts. Acid–Base Properties of 3,5-Bis(nitroamino)-1,2,4-triazole
  作者：E. L. Metelkina

  DOI：10.1023/b:rujo.0000036077.24894.51

  日期：2004.4

  Heterocyclization of hydrazine-1,2-bis(N-2-nitrocarboximidamide) and salts derived therefrom provides a procedure for the synthesis of 3,5-bis(nitroamino)-1,2,4-triazole salts. The presence of two acceptor nitroamino groups conjugated with the triazole ring considerably enhances the acidity of 3,5-bis(nitroamino)-1,2,4-triazole (pK(a)(1) = -2.0, pK(a)(2) = 4.8, pK(a)(3) = 10.6) as compared to mononitroaminotriazole, so that formation of salts with the corresponding dianion becomes possible.