methylborane | 12538-96-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: methylborane
• 英文别名: Methyl-boran；InChI=1/CH5B/c1-2/h2H2,1H
• CAS: 12538-96-4
• 化学式: CH₅B
• 分子量: 27.8617
• InChiKey: PLFLRQISROSEIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.33
• 重原子数：
  2
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  methylborane 在 三苯基膦 作用下， 生成
  参考文献：
  名称：

  Bestmann, Hans Juergen; Suehs, Kurt; Roeder, Thomas, Angewandte Chemie, 1981, vol. 93, # 12, p. 1098 - 1100

  摘要：

  DOI：
• 作为产物：
  描述：

  在 MeI or benzyliodide 作用下， 以 四氢呋喃 为溶剂， 生成 methylborane
  参考文献：
  名称：

  Bestmann, Hans Juergen; Suehs, Kurt; Roeder, Thomas, Angewandte Chemie, 1981, vol. 93, # 12, p. 1098 - 1100

  摘要：

  DOI：
• 作为试剂：
  描述：

  1-己烯 、 1,1-二氯甲醚 在 methylborane 作用下， 生成 仲辛酮
  参考文献：
  名称：

  Hydroboration. 87. Controlled and sequential hydroboration of simple representative alkenes with methylborane in tetrahydrofuran. An examination of the directive effects in the first and second stages of hydroboration

  摘要：

  DOI：

  10.1021/jo00304a017

文献信息

• Hydrides of Boron. VI. The Action of Ammonia on the Methyl Diboranes
  作者：H. I. Schlesinger、Leo Horvitz、A. B. Burg

  DOI：10.1021/ja01294a008

  日期：1936.3
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: B: SVol.1, 4.8.3, page 219 - 224
  作者：

  DOI：——

  日期：——
• Hydrides of Boron. XII. Symmetrical Dimethyldiborane and the Methyl Derivatives of Borine Trimethylammine
  作者：H. I. Schlesinger、Nestor W. Flodin、Anton B. Burg

  DOI：10.1021/ja01874a026

  日期：1939.5
• Hydroboration. 79. Preparation and properties of methylborane and dimethylborane and their characteristics as hydroborating agents. Synthesis of tertiary alcohols containing methyl groups via hydroboration
  作者：Herbert C. Brown、Thomas E. Cole、Morris Srebnik、Kee Won Kim

  DOI：10.1021/jo00375a031

  日期：1986.12
• Thermal stability and kinetics of ylide-borane complexes
  作者：Jonathan M. Stoddard、Kenneth J. Shea

  DOI：10.1016/j.tca.2004.05.024

  日期：2004.12

  Complexes of dimethylsulfoxonium methylide (1) and organoboranes are crystalline for ylide(.)BH(3) (2), ylide(.)BPh(3) (3), ylide(.)B(C6F5)(3) (4), and ylide(.)BF(3) (5). These complexes undergo exothermic rearrangement by 1,2-migration upon heating to produce homologated organoboranes and dimethylsulfoxide. Non-isothermal kinetic analysis of the differential scanning calorimetry (DSC) data for ylide(.)BPh(3) (3) and ylide(.)B(C6F5)(3) (4) complexes was applied using the Flynn-Wall-Ozawa and Kissinger methods. The calculated apparent activation energy for the reaction of ylide(.)BPh(3) (3) yielded consistent results between the A(1.5) model (E-a = 120 kJ mol(-1), A = 4.79 x 10(13) min(-1)) and Kissinger method (E-a = 129 kJ mol(-1), A = 1.73 x 10(17) min(-1)). The analysis for the reaction of ylide(.)B(C6F5)(3) (4) gave consistent results between R-2, R-3, and F-1 models with the average parameters, E-a = 262 kJ mol(-1), A = 3.33 x 10(33) min(-1). The Kissinger analysis for the reaction of ylide(.)B(C6F5)(3) (4) gave Arrhenius activation parameters (E-a = 171 kJ mol(-1), A = 7.80 x 10(19) min(-1)) that were higher than for the reaction of ylide(.)BPh(3) (3). The kinetic data revealed that the C6F5 electron-deficient group has a higher activation energy for 1,2-migration and a higher entropy of activation for 1,2-migration than the C6H5 group. HF/6-31G(d) ab initio calculations agree with the kinetic data. (C) 2004 Elsevier B.V. All rights reserved.