1,2-二硝基胍 | 666736-83-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 1,2-二硝基胍
• 英文名称: 1,2-dinitroguanidine
• 英文别名: Dinitroguanidine；1,3-dinitroguanidine
• CAS: 666736-83-0
• 化学式: CH₃N₅O₄
• 分子量: 149.066
• InChiKey: ULLQXGARUROVCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  142
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,2-二硝基胍 在 氢氧化钾 、 一水合肼 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以88%的产率得到2,5-dinitrobiguanidine
  参考文献：
  名称：

  摘要：

  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.

  DOI：

  10.1023/a:1026003700547
• 作为产物：
  描述：

  硝基胍 在 硫酸 、 三氧化硫 、 硝酸 作用下， 生成 1,2-二硝基胍
  参考文献：
  名称：

  Synthesis and Characteristics of Energetic Materials Based on 1,2-Dinitroguanidine

  摘要：

  成功合成了一系列基于 1,2-二硝基胍的高能盐，并使用 1H NMR、13C NMR 和 IR 光谱、质谱、元素分析和差示扫描量热法对其进行了全面表征。结果表明，与三硝基甲苯（TNT，2,4,6-三硝基甲苯）相比，所有盐类都具有更高的起爆特性（起爆压力和速度分别为 24.8 至 30.3 GPa 和 7665 至 8422 m s-1）。为了更好地了解这些高能盐的物理和化学特性，还对其热稳定性和热动力学参数进行了研究。

  DOI：

  10.1071/ch14060

文献信息

• Structure, Thermal Behaviour, and Energetic Properties of 4-Amino-1,2,4-triazole Dinitroguanidine Salt
  作者：Xinghui Jin、Bingcheng Hu、Huanqing Jia、Zuliang Liu、Chunxu Lu

  DOI：10.1071/ch13426

  日期：——

  A novel nitrogen-rich energetic compound 4-amino-1,2,4-triazole dinitroguanidine salt (4-ATDNG) was synthesized and fully characterized. Its crystal, thermal behaviour, and detonation properties were investigated by X-ray diffraction, thermogravimetry-derivative thermogravimetry-differential scanning calorimetry (TG-DTG-DSC) coupling system, and the Kamlet–Jacobs equation. In view of the obtained values such as the critical temperature of thermal explosion (Tb, 186.36°C), entropy of activation (ΔS≠, 60.22 J mol–1 k–1), enthalpy of activation (ΔH≠, 143.24 kJ mol–1), free energy of activation (ΔG≠, 116.34 kJ mol–1), detonation pressure (P, 29.78 GPa), detonation velocity (V, 8.28 km s–1), and impact sensitivity (h50 = 135 cm), it is proposed that 4-ATDNG possesses excellent thermal stability and has the potential to be a useful energetic material in the future.

  合成了一种新型富氮高能化合物 4-氨基-1,2,4-三唑二硝基胍盐（4-ATDNG），并对其进行了全面表征。通过 X 射线衍射、热重法-衍生热重法-差示扫描量热法（TG-DTG-DSC）耦合系统和 Kamlet-Jacobs 方程研究了其晶体、热行为和引爆特性。根据所获得的热爆炸临界温度（Tb，186.36°C）、活化熵（ΔS≠，60.22 J mol-1 k-1）、活化焓（ΔH≠，143.24 kJ mol-1）、活化自由能（ΔG≠，116.34 kJ mol-1）、爆轰压力（P，29.78 GPa）、爆轰速度（V，8.28 km s-1）和冲击灵敏度（h50 = 135 cm），表明 4-ATDNG 具有优异的热稳定性，有望成为未来有用的高能材料。
• 一种1-甲基-1,2-二硝基胍的制备方法
  申请人：南通天泽化工有限公司

  公开号：CN109053498A

  公开（公告）日：2018-12-21

  本发明公开了一种1‑甲基‑1,2‑二硝基胍的制备方法，本发明采用硝基胍、硝酸、浓硫酸、硝酸铵经硝化反应得到1,2‑二硝基胍，1,2‑二硝基胍在碳酸钾的存在下，再与甲胺反应生成1‑甲基‑1,2‑二硝基胍。所述反应步骤包括：将96％硝酸、20％发烟硫酸与少量硝酸铵配成混酸后降温，然后将溶有硝基胍的硝酸溶液缓慢滴加到混酸中，滴完后保温一段时间得到1,2‑二硝基胍，再将1,2‑二硝基胍投入碳酸钾水溶液中，滴加甲胺水溶液完毕后保温一段时间后得到产品1‑甲基‑1,2‑二硝基胍，后处理经过滤、洗涤、重结晶、干燥得到1‑甲基‑1,2‑二硝基胍固体。本发明的方法制备的1‑甲基‑1,2‑二硝基胍纯度高、杂质含量少、摩尔收率高，取得了良好的经济效益；制备方法安全、环保，适用于工业生产。
• Two Outstanding Explosives Based on 1,2-Dinitroguanidine: Ammonium- dinitroguanidine and 1,7-Diamino-1,7-dinitrimino-2,4,6-trinitro-2,4,6-triazaheptane
  作者：Thomas Altenburg、Thomas M. Klapötke、Alexander Penger、Jörg Stierstorfer

  DOI：10.1002/zaac.200900560

  日期：2010.3

  sensitive towards mechanical stimuli (IS ≥ 5J, FS = 160 N). The detonation parameters (EXPLO5 code) were calculated using combined quantum chemical (CBS-4M) methods and a chemical equilibrium calculation based on the steady-state model of detonation: ADNQ (Vdet = 9066 m·s–1, pC–J = 332 kbar, Qv = –5193 kJ·kg–1), APX (Vdet = 9540 m·s–1, pC–J = 395 kbar, Qv = –5935 kJ·kg–1). The experimentally determined detonation

  铵-二硝基胍 (ADNQ) 和 1,7-diamino-1,7-dinitrimino-2,4,6-trinitro-2,4,6-triazaheptane (APX) 已以高产率和纯度合成。两种化合物均通过多核 NMR（1H、13C、14N）和振动光谱进行表征。通过单晶X射线衍射阐明了分子结构。ADNQ 在单斜空间群 P21/c 中结晶，晶体密度为 ρ = 1.735 g·cm-3，APX 在正交空间群 Pbnc 中结晶，晶体密度为 ρ = 1.911 g·cm-3。ADNQ 在 197 °C 分解，APX 在 174 °C 分解。两种化合物的冲击 (IS)、摩擦 (FS) 和静电放电 (ESD) 敏感性均通过实验确定。（ADNQ：IS ≥ 10 J，FS ≥ 252 N 和 ESD ≥ 0.4 J，APX：IS ≥ 3 J，FS ≥ 80 N 和 ESD ≥ 0.1 J）。事实证明，APX
• ——
  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.
• Synthesis and Characteristics of Energetic Materials Based on 1,2-Dinitroguanidine
  作者：Bingcheng Hu、Xinghui Jin、Huanqing Jia、Zuliang Liu、Chunxu Lv

  DOI：10.1071/ch14060

  日期：——

  A series of energetic salts based on 1,2-dinitroguanidine were successfully synthesised and fully characterised using 1H NMR, 13C NMR, and IR spectroscopy, mass spectrometry, elemental analysis, and differential scanning calorimetry. The results show that all the salts possess higher detonation properties (detonation pressures and velocities ranging from 24.8 to 30.3 GPa and 7665 to 8422 m s–1, respectively) than those of trinitrotolouene (TNT, 2,4,6-trinitromethylbenzene). The thermal stability and thermal kinetic parameters were also investigated to give a better understanding of the physical and chemical properties of these energetic salts.

  成功合成了一系列基于 1,2-二硝基胍的高能盐，并使用 1H NMR、13C NMR 和 IR 光谱、质谱、元素分析和差示扫描量热法对其进行了全面表征。结果表明，与三硝基甲苯（TNT，2,4,6-三硝基甲苯）相比，所有盐类都具有更高的起爆特性（起爆压力和速度分别为 24.8 至 30.3 GPa 和 7665 至 8422 m s-1）。为了更好地了解这些高能盐的物理和化学特性，还对其热稳定性和热动力学参数进行了研究。