1,3-dibromo-5-(trimethylsilyloxy)benzene | 856766-98-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,3-dibromo-5-(trimethylsilyloxy)benzene
• 英文别名: 3,5-Dibromophenoxytrimethylsilane；(3,5-dibromophenoxy)-trimethylsilane
• CAS: 856766-98-8
• 化学式: C₉H₁₂Br₂OSi
• 分子量: 324.087
• InChiKey: DOMHKFJZPMCOIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,3-dibromo-5-(trimethylsilyloxy)benzene 在 lithium diisopropyl amide 、 碘 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 生成 3,5-dibromo-4-iodophenyjl
  参考文献：
  名称：

  A study on the metalation of alkoxydibromobenzenes

  摘要：

  The metalation of (quasi)alkoxy-substituted dibromobenzenes C6H3(OR)Br-2 with lithium diisopropylamide (LDA) has been investigated. For 1-(quasi)alkoxy-3,5-dibromobenzenes (R = Me, TMS), different selectivities were observed depending on reaction conditions and the size of the alkoxy group. The methoxy group was an effective ortho-director whereas this was not the case for the bulky trimethylsilyloxy group. The metalation of related 2,5-dibromoanisole was also examined showing a significant meta-directing effect by the methoxy group. The thermal stability of aryllithium intermediates is significantly lower when lithium is flanked by a bromine and a methoxy group, whereas 4-(quasi)alkoxy-2,6-dibromoaryllithiums are less labile. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.04.065
• 作为产物：
  描述：

  六甲基二硅烷 、 3,5-二溴苯酚 反应 0.5h， 以95%的产率得到1,3-dibromo-5-(trimethylsilyloxy)benzene
  参考文献：
  名称：

  A study on the metalation of alkoxydibromobenzenes

  摘要：

  The metalation of (quasi)alkoxy-substituted dibromobenzenes C6H3(OR)Br-2 with lithium diisopropylamide (LDA) has been investigated. For 1-(quasi)alkoxy-3,5-dibromobenzenes (R = Me, TMS), different selectivities were observed depending on reaction conditions and the size of the alkoxy group. The methoxy group was an effective ortho-director whereas this was not the case for the bulky trimethylsilyloxy group. The metalation of related 2,5-dibromoanisole was also examined showing a significant meta-directing effect by the methoxy group. The thermal stability of aryllithium intermediates is significantly lower when lithium is flanked by a bromine and a methoxy group, whereas 4-(quasi)alkoxy-2,6-dibromoaryllithiums are less labile. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.04.065

文献信息

• Selective recovery of a pyridine derivative from an aqueous waste stream containing acetic acid and succinonitrile with solvent impregnated resins
  作者：J. Bokhove、T.J. Visser、B. Schuur、A.B. de Haan

  DOI：10.1016/j.reactfunctpolym.2014.11.007

  日期：2015.1

  Solvent impregnated resins (SIRs) were evaluated for the recovery of pyridine derivatives from an aqueous waste-stream containing also acetic acid and succinonitrile. For this purpose, a new solvent was developed, synthesized and impregnated in Amberlite XAD4. Sorption studies were used to determine the capacity, selectivity and the mass-transfer rate. A high capacity of 21 g 4-cyanopyridine (CP) per kg SIR was found, with very high selectivity toward CP over the other solutes of at least 570. A modified Langmuir equation could describe the equilibrium sorption isotherm. Both the linear driving force model and a Fickian diffusion model were evaluated. The Fick-model described both regeneration and loading best. The CP-diffusivity through the solvent phase was estimated at 6.53.10(-13) +/- 2.5% m(2) s(-1). The model was validated using fixed-bed column experiments. The R-2 values for this model ranged between 0.94 at a flow rate of 5 mL/min and 0.99 at a flow rate of 1 mL/min during the loading cycle. Due to mass-transfer limitations the breakthrough profiles were broad and breakthrough occurred after 5 or 23 bed volumes, for flow rates of 5 and 1 mL/min, respectively. Both acetic acid and succinonitrile broke through immediately due to the very high CP-selectivity of the SIR. (C) 2014 Elsevier B.V. All rights reserved.
• A study on the metalation of alkoxydibromobenzenes
  作者：Marek Da˛browski、Joanna Kubicka、Sergiusz Luliński、Janusz Serwatowski

  DOI：10.1016/j.tetlet.2005.04.065

  日期：2005.6

  The metalation of (quasi)alkoxy-substituted dibromobenzenes C6H3(OR)Br-2 with lithium diisopropylamide (LDA) has been investigated. For 1-(quasi)alkoxy-3,5-dibromobenzenes (R = Me, TMS), different selectivities were observed depending on reaction conditions and the size of the alkoxy group. The methoxy group was an effective ortho-director whereas this was not the case for the bulky trimethylsilyloxy group. The metalation of related 2,5-dibromoanisole was also examined showing a significant meta-directing effect by the methoxy group. The thermal stability of aryllithium intermediates is significantly lower when lithium is flanked by a bromine and a methoxy group, whereas 4-(quasi)alkoxy-2,6-dibromoaryllithiums are less labile. (c) 2005 Elsevier Ltd. All rights reserved.