8,9-diiodo-1,2-dicarba-closo-dodecarborane(12) | 29386-25-2

• 英文名称: 8,9-diiodo-1,2-dicarba-closo-dodecarborane(12)
• 英文别名: 8,9-diiodo-1,2-dicarba-closo-dodecaborane；9,12-I2-1,2-C2B10H10；8,9-I2-1,2-closo-C2B10H10
• CAS: 29386-25-2
• 化学式: C₂H₁₀B₁₀I₂
• 分子量: 396.02
• InChiKey: MUUFDDISJXCNTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  8,9-diiodo-1,2-dicarba-closo-dodecarborane(12) 、 9,12-diiodo-1,2-dicarba-closo-dodecarborane(12) 、 碘 在 HNO₃ 、 H₂SO₄ 作用下， 以 溶剂黄146 为溶剂， 生成 8,9,10,12-tetraiodo-1,2-dicarba-closo-dodecaborane(12) 、 8,9,12-triiiodo-1,2-dicarba-closo-dodecaborane
  参考文献：
  名称：

  Synthesis and deborination of polyhalo-substituted ortho-carboranes

  摘要：

  Tetraiodo-1,2-dicarba-closo-dodecaborane and 9-bromo-8,10,12-triiodo-1,2-dicarba-closo-dodecaborane were synthesized by oxidative iodination of 1,2-dicarba-closo-dodecaborane and 9-bromo-1,2-dicarba-closo-dodecaborane, respectively, in AcOH using a mixture of nitric and sulfuric acid as an oxidant of iodine. The intermediates in the ortho-carborane iodination were identified. By the action of elemental bromine on 9-iodo-1,2-dicarba-closo-dodecaborane in the presence of aluminum chloride catalyst 9-iodo-8,10,12-tribromo-1,2-dicarba-closo-dodecaborane was obtained. Deborination of the synthesized substances with an alcohol solution of KOH led to formation of 1,5,6,10-tetraiodo-5-bromo-1,6,10-triiodo- and 5-iodo-1,6,10-tribromo-7,8-dicarbaundecaborates methylammonium salts.

  DOI：

  10.1134/s1070363211060107
• 作为产物：
  描述：

  1,2-dicarba-closo-dodecaborane(12) 、 碘 在 HNO₃ 、 H₂SO₄ 作用下， 以 溶剂黄146 为溶剂， 以82%的产率得到9,12-diiodo-1,2-dicarba-closo-dodecarborane(12)
  参考文献：
  名称：

  9,12-Diiodo-1,2-dicarba-closo-dodecaborane(12)

  摘要：

  The title compound, C2H10B10I2, has a pseudo-icosahedral cluster geometry. The crystal structure features an intermolecular C-H...I-B hydrogen bond with a normalized H...I distance of 3.00 Angstrom.

  DOI：

  10.1107/s0108270102023582

文献信息

• A solvent-free regioselective iodination route of ortho-carboranes
  作者：Albert Vaca、Francesc Teixidor、Raikko Kivekäs、Reijo Sillanpää、Clara Viñas

  DOI：10.1039/b612465h

  日期：——

  Tetraiodo-ortho-carborane based X-ray contrast agents can be readily prepared in a high yield, fast, clean, regioselective fashion by a solvent-free reaction of ortho-carboranes with iodine in sealed tubes.

  原硼烷与碘在密封管中进行无溶剂反应，可轻松制备出高产、快速、清洁和具有区域选择性的四碘原硼烷基 X 射线造影剂。
• Designed Synthesis of New <i>ortho</i>-Carborane Derivatives: from Mono- to Polysubstituted Frameworks
  作者：Gemma Barberà、Albert Vaca、Francesc Teixidor、Reijo Sillanpää、Raikko Kivekäs、Clara Viñas

  DOI：10.1021/ic800362z

  日期：2008.8.1

  The use of nucleophilic and electrophilic processes allow the designed synthesis of several B-iodinated derivatives of o-carborane. Because of the straightforward Pd-catalyzed conversion of B-I to B-C bond with Grignard reagents, such as methylMgBr and biPhenylMgBr, both, symmetrical 3,6-R-2-1,2-closo-C2B10H10 and asymmetrical 3-1-6-Me-1,2-closo-C2B10H10 could be obtained. Not only conventional reactions in solution have been studied but also a highly efficient, clean and fast solvent-free procedure has provided successful results to regioselectively produce B-iodinated o-carborane derivatives by a careful control of the reaction conditions. The high number of nonequivalent leaving groups in boron iodinated o-carborane derivatives opens the possibility through B-C coupling to materials with novel possibilities and to self-assembling due to the enhanced polarizability of the C-H bond.