N-(氯甲基)-N'-{[(氯甲基)(硝基)氨基]甲基}-N,N'-二硝基甲二胺 | 13126-17-5

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: N-(氯甲基)-N'-{[(氯甲基)(硝基)氨基]甲基}-N,N'-二硝基甲二胺
• 英文名称: 1,7-dichloro-2,4,6-triaza-2,4,6-trinitroheptane
• 英文别名: 1,7-dichloro-2,4,6-trinitro-2,4,6-triazaheptane；bis-[(chloromethyl-nitro-amino)-methyl]-nitro-amine；1,5-Bis-chlormethyl-1,3,5-trinitro-dimethylentriamin；Bis-[(chlormethyl-nitro-amino)-methyl]-nitro-amin；1.7-Dichlor-2.4.6-trinitro-2.4.6-triaza-heptan；1,7-Dichlor-2,4,6-trinitro-2,4,6-triaza-heptan；Methanediamine, N-(chloromethyl)-N'-(((chloromethyl)nitroamino)methyl)-N,N'-dinitro-；N,N-bis[[chloromethyl(nitro)amino]methyl]nitramide
• CAS: 13126-17-5
• 化学式: C₄H₈Cl₂N₆O₆
• 分子量: 307.05
• InChiKey: IQYWQRXBDCKWIL-UHFFFAOYSA-N

物化性质

• 沸点：
  650.2±55.0 °C(Predicted)
• 密度：
  1.730±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  147
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-(氯甲基)-N'-{[(氯甲基)(硝基)氨基]甲基}-N,N'-二硝基甲二胺 在 甲醇 作用下， 生成 bis-[(methoxymethyl-nitro-amino)-methyl]-nitro-amine
  参考文献：
  名称：

  Tetramethylenetrinitramine Trifluoroacetates

  摘要：

  DOI：

  10.1021/ja01585a026
• 作为产物：
  描述：

  bis-[(methoxymethyl-nitro-amino)-methyl]-nitro-amine 在 乙酰氯 、 zinc(II) chloride 作用下， 生成 N-(氯甲基)-N'-{[(氯甲基)(硝基)氨基]甲基}-N,N'-二硝基甲二胺
  参考文献：
  名称：

  Majer,J.; Denkstein,J., Collection of Czechoslovak Chemical Communications, 1966, vol. 31, p. 2547 - 2557

  摘要：

  DOI：

文献信息

• Energy and Biocides Storage Compounds: Synthesis and Characterization of Energetic Bridged Bis(triiodoazoles)
  作者：Chunlin He、Gang Zhao、Joseph P. Hooper、Jean’ne M. Shreeve

  DOI：10.1021/acs.inorgchem.7b02277

  日期：2017.11.6

  reacting potassium triiodopyrazolate or triiodoimidazolate with corresponding dichloro compounds. All compounds were fully characterized by 1H and 13C NMR spectroscopy, IR spectroscopy, and elemental analyses. The structure of compound 1 was further confirmed by single-crystal X-ray diffraction. All of the compounds exhibit good thermal stability with decomposition temperatures between 199 and 270 °C

  高能桥联的三碘吡唑和三碘咪唑的设计和合成是通过使三碘吡唑钾或三碘咪唑钾与相应的二氯化合物反应来进行的。所有化合物均通过1 H和13 C NMR光谱，IR光谱和元素分析充分表征。化合物1的结构通过单晶X射线衍射进一步确认。所有化合物均表现出良好的热稳定性，分解温度在199至270°C之间，密度在2.804至3.358 g / cm 3范围内。爆轰性能和爆轰产物由CHEETAH 7计算。化合物3（D v = 4765 ms –1; P = 17.9 GPa）和化合物7（D v = 4841 ms –1；P = 18.5 GPa）显示出与TNT相当的爆轰压力，高碘含量使其成为能量和杀生物剂的储存化合物。
• Process for producing N-chloromethyl nitramines
  申请人：The United States of America as represented by the Secretary of the Navy

  公开号：US05243075A1

  公开（公告）日：1993-09-07

  1-acetoxy-2,4,6-trinitro-2,4,6-triazaheptane, 1,7-diacetoxy-2,4,6-trinitro-2,4,6-triazaheptane, or 1,9-diacetoxy-2,4,6,8-tetranitro-2,4,6,8-tetraazanonane is reacted with a mixture of concentrated hydrochloric acid and trifluoroacetic 2,4,6-triazaheptane, 1,7-dichloro-2,4,6-trinitro-2,4,6-triazaheptane, or 1,7-dichloro-2,4,6,8-tetranitro-2,4,6,8-tetraazanonane.

  1-乙酰氧基-2,4,6-三硝基-2,4,6-三氮杂庚烷，1,7-二乙酰氧基-2,4,6-三硝基-2,4,6-三氮杂庚烷或1,9-二乙酰氧基-2,4,6,8-四硝基-2,4,6,8-四氮杂壬烷与浓盐酸和三氟乙酸混合反应，生成1,7-二氯-2,4,6-三硝基-2,4,6-三氮杂庚烷，1,7-二氯-2,4,6,8-四硝基-2,4,6,8-四氮杂壬烷。
• Investigation and Characterization of Nitrazapropane‐, Oxapropane‐ and Trinitrazaheptane‐Bridged Nitro Esters
  作者：Jasmin T. Lechner、Christian Riedelsheimer、Nina M. Gerold、Jennifer Heidrich、Burkhard Krumm、Jörg Stierstorfer、Thomas M. Klapötke

  DOI：10.1002/ejoc.202300890

  日期：2023.12.13

  Starting from a modified Bachmann procedure, which is commonly used for the synthesis of RDX and HMX, two new nitro esters were synthesized and investigated, 1,3-dinitroxy-2-nitrazapropane and 1,7-dinitroxy-2,4,6-trinitrazaheptane. Furthermore, the structural similar compound 1,3-dinitroxy-2-oxapropane was obtained. All compounds were comprehensivly characterized and compared to commonly used explosives

  从常用于合成 RDX 和 HMX 的改进巴赫曼程序开始，合成并研究了两种新的硝基酯：1,3-二硝基氧基-2-硝氮丙烷和 1,7-二硝基氧基-2,4,6-三硝基氮杂庚烷。此外，还得到了结构相似的化合物1,3-二硝基氧基-2-氧杂丙烷。对所有化合物进行了全面表征，并在其物理化学性质和爆炸行为方面与常用炸药进行了比较。
• Dipropargyl ethers possessing nitramine units
  作者：Pavel S. Gribov、Tat'yana S. Kon'kova、Kyrill Yu. Suponitsky、Aleksei B. Sheremetev

  DOI：10.1016/j.mencom.2023.06.008

  日期：2023.7

  The syntheses and characterization of novel propargyl ethers of N-(hydroxymethyl)nitramines that contain from one to four nitramine units are reported. All nitramine-functionalized ethers were well characterized by IR and multinuclear NMR spectroscopy as well as CHN analysis, and the X-ray crystal structures of two of them are described. For ethers bearing two or three nitramine units, the standard molar

  报道了含有 1 至 4 个硝胺单元的新型N- (羟甲基)硝胺炔丙醚的合成和表征。所有硝胺官能化醚均通过红外光谱、多核核磁共振光谱以及CHN分析进行了表征，并描述了其中两种的X射线晶体结构。对于带有两个或三个硝胺单元的醚，在 298.15 K 时的标准摩尔形成焓是通过静态弹燃烧量热法测量的氧气中燃烧的实验标准摩尔能确定的
• Synthesis of Bridged Tetrazoles with Promising Properties and Potential Applications by a One‐Step Finkelstein Reaction
  作者：Jasmin T. Lechner、Christian Riedelsheimer、Simon M. J. Endraß、Nina M. Gerold、Jennifer Heidrich、Burkhard Krumm、Jörg Stierstorfer、Thomas M. Klapötke

  DOI：10.1002/chem.202303021

  日期：2024.1.2

  Numerous nitramine bridged compounds which show promising combinations of properties have already been identified in the area of energetic materials. In this work, four new nitrazapropane bridged tetrazoles, as well as four new trinitrazaheptane tetrazoles and three oxapropane bridged tetrazoles were synthesized and fully characterized. These new compounds can all be synthesized by a simple, one‐step synthesis using Finkelstein conditions. All of these new energetic materials were characterized using NMR spectroscopy, single crystal X‐ray diffraction, vibrational analysis and elemental analysis. The thermal behaviour of these compounds was studied by differential thermal analysis (DTA) and partly by thermogravimetric analysis (TGA). The BAM standard method was used to determine the sensitivities towards impact (IS) and friction (FS). The enthalpies of formation were calculated at the CBS‐4M level, and the energetic performances were calculated using the EXPLO5 (V6.06.01) computer code. The properties of the new compounds were compared to each other as well as to the known energetic material RDX. Moreover, the iron(II) and copper(II) perchlorate complexes with 1,3‐bis‐1,1‐tetrazolylnitrazapropane as ligand were prepared and investigated.

  摘要 在高能材料领域已经发现了许多具有良好综合特性的硝胺桥化合物。在这项工作中，合成了四种新的硝基丙烷桥联四唑、四种新的三硝基庚烷四唑和三种氧代丙烷桥联四唑，并对其进行了全面表征。这些新化合物均可在芬克尔斯坦条件下通过简单的一步合成法合成。利用核磁共振光谱、单晶 X 射线衍射、振动分析和元素分析对所有这些新型高能材料进行了表征。对这些化合物的热性能研究采用了差热分析（DTA），部分采用了热重分析（TGA）。采用 BAM 标准方法确定了对冲击（IS）和摩擦（FS）的敏感性。形成焓在 CBS-4M 水平上进行了计算，能量性能则使用 EXPLO5（V6.06.01）计算机代码进行了计算。新化合物的特性与已知高能材料 RDX 进行了比较。此外，还制备并研究了以 1,3-bis-1,1-tetrazolylnitrazapropane 为配体的高氯酸盐铁（II）和铜（II）配合物。