1,1,4,4-四硝基-2,3-丁二醇 | 78800-72-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 中文名称: 1,1,4,4-四硝基-2,3-丁二醇
• 英文名称: 1,1,4,4-tetranitro-2,3-butanediol
• 英文别名: 1,1,4,4-tetranitrobutane-2,3-diol；1,1,4,4-tetranitrobutan-2,3-diol
• CAS: 78800-72-3
• 化学式: C₄H₆N₄O₁₀
• 分子量: 270.112
• InChiKey: SHJMOUMCQLBKLM-UHFFFAOYSA-N

物化性质

• 熔点：
  139 °C
• 沸点：
  453.5±45.0 °C(Predicted)
• 密度：
  1.899±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  224
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,1,4,4-四硝基-2,3-丁二醇 在 溴 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 1.0h， 以32.2%的产率得到1,1,4,4-tetranitro-1,4-dibromo-2,3-butanediol
  参考文献：
  名称：

  1,1,4,4-tetranitrobutane-2,3-diol and its derivatives. 2. Chlorination and bromination of 1,1,4,4-tetranitrobutane-2,3-diol. crystal structure of halogen derivatives of 1,1,4,4-tetranitrobutane-2,3-diol

  摘要：

  The bromination of 1,1,4,4-tetranitrobutane-2,3-diol in 60% acetic acid gave 1,4-dibromo-1,1,4,4-tetranitrobutane-2,3-diol in satisfactory yield. The chlorination of 1,1,4,4-tetranitrobutane-2,3-diol under analogous conditions gave 1,4-dichloro-1,1,4,4-tetranitrobutane-2,3-diol as a crystal hydrate. Drying of this latter product in vacuum over phosphorus pentoxide gave 1,4-dichloro-1,1, 4,4-tetranitrobutane-2,3-diol in quantitative yield. The structures of these products were determined by x-ray diffraction structural analysis. The crystal chemical analysis and quantum chemical calculations established an increase in secondary oxygen-halogen interactions in the halodinitromethyl fragment with increasing atomic number of the halogen atom.

  DOI：

  10.1007/bf00963510
• 作为产物：
  描述：

  1,1,4,4-tetranitro-2,3-butanediol disodium salt 在 sodium hydroxide 、 硫酸 作用下， 以 乙醚 为溶剂， 生成 1,1,4,4-四硝基-2,3-丁二醇
  参考文献：
  名称：

  Nekrasova, G. V.; Lipina, E. S.; Zagibalova, L. Ya., Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, # 4, p. 619 - 623

  摘要：

  DOI：

文献信息

• Gem-dinitro compounds in organic synthesis. 4. Use of the condensation product of glyoxal and dinitromethane in the synthesis of nitro-1,2,3-triazoles
  作者：A. T. Baryshnikov、V. I. Erashko、N. I. Zubanova、B. I. Ugrak、S. A. Shevelev、A. A. Fainzilberg、V. V. Semenov

  DOI：10.1007/bf00863589

  日期：1992.9

  The condensation of dinitromethane with glyoxal has been investigated and it has been demonstrated that 1,1,4,4-tetranitro-2,3-butandiol, alpha-hydroxy-beta,beta-dinitropropionic acid or their mixture may be formed. Interaction of 1,1,4,4-tetranitro-2,3-butandiol or 1,4-dibromo-1,1,4,4-tetranitro-2,3-butanediol diacetates with sodium azide leads to bis(5-nitro-1,2,3-triazol-4-yl) via intermediate 1, 1,4,4-tetranitro-1,3-butadiene.
• 1,1,4,4-Tetranitrobutane-2,3-diol and its derivatives. 5. Reaction of 1,1,4,4-tetranitrobutane-2,3-diol with formaldehyde; synthesis and crystal structure of 4,4-dinitro-2,3-dihydroxytetrahydrofuran
  作者：B. S. Fedorov、N. I. Golovina、L. S. Barinova、V. V. Arakcheeva、G. V. Lagodzinskaya、M. V. Loginova、R. F. Trofimova、V. Z. Laishev、V. F. Lazarev、S. P. Smirnov、I. Sh. Abdrakhmanov、A. I. Firkin、L. O. Atovmyan

  DOI：10.1007/bf01150743

  日期：1992.12

  1,1,4,4-Tetranitrobutane-2,3-diol reacts with formaldehyde, forming 2,2-dinitropropane-1,3-diol or a cyclic ether - 4,4-dinitro-2,3-dihydroxytetrahydrofuran - as a function of the reaction conditions.
• 1,1,4,4-Tetranitrobutane-2,3-diol and its derivatives. 1. Reaction of dinitromethane potassium salt with glyoxal. Crystal structure of 1,1,4,4-tetranitrobutane-2,3-diol and its diacetate
  作者：B. S. Fedorov、N. I. Golovina、L. S. Barinova、R. F. Trofimova、V. V. Arakcheeva、L. O. Atovmyan

  DOI：10.1007/bf00958562

  日期：1991.4

  The synthesis of 1,1,4,4-tetranitrobutane-2,3-diol has been carried out via the reaction of the dinitromethane potassium salt with glyoxal, at pH values of 7-8 after reagent mixing and 5.5 at the end of the reaction, in the temperature range 35-37-degrees-C. X-ray crystal structure analysis has been performed on 1,1,4,4-tetranitrobutane-2,3-diol and its diacetate. The conformations of these molecules are stabilized to a significant extent by O-...N+-type electrostatic interaction, which was confirmed by quantum-mechanical calculations on 2,2-dinitroethanol as a model molecule.
• 1,1,4,4-Tetranitrobutane-2,3-diol and its derivatives. 4. Study of the reaction of 1,1,4,4-tetranitrobutane-2,3-diol with N-(methoxymethyl)-2-fluoro-2,2-dinitroethylamine; synthesis and crystalline structure of 1,12-difluoro-1,1,3,5,5,8,8,10,12,12-decanitro-3,10-diazadodecane-6,7-diol dinitrate
  作者：B. S. Fedorov、N. I. Golovina、V. V. Arakcheeva、G. V. Shilov、L. O. Atovmyan

  DOI：10.1007/bf00863077

  日期：1992.3

  A two-step has been proposed to obtain 1,12-difluoro-1,1,3,5,5,8,8,10,12,12-decanitro-3,10-diazadodecane-6,7-diol dinitrate, starting from 1,1,4,4-tetranitrobutane-2,3-diol and N-(methoxymethyl)-2-fluoro-2,2-dinitroethylamine, followed by nitration of the Mannich base formed. An x-ray-diffraction investigation of the dinitrate obtained was carried out.
• FEDOROV, B. S.;GOLOVINA, N. I.;BARINOVA, L. S.;TROFIMOVA, R. F.;ARAKCHEEV+, IZV. AN CCCP. CEP. XIM.,(1991) N, S. 830-834
  作者：FEDOROV, B. S.、GOLOVINA, N. I.、BARINOVA, L. S.、TROFIMOVA, R. F.、ARAKCHEEV+

  DOI：——

  日期：——