5-bromo-1,10-phenanthroline-2,9-dicarbaldehyde | 1007105-17-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 5-bromo-1,10-phenanthroline-2,9-dicarbaldehyde
• CAS: 1007105-17-0
• 化学式: C₁₄H₇BrN₂O₂
• 分子量: 315.126
• InChiKey: HLPVACDDTPBFHI-UHFFFAOYSA-N

物化性质

• 熔点：
  227 °C (decomp)
• 沸点：
  548.7±45.0 °C(Predicted)
• 密度：
  1.716±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-bromo-1,10-phenanthroline-2,9-dicarbaldehyde 在 吡啶 、 盐酸羟胺 、 一水合肼 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 、 乙醇 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Immobilisation of Phenanthroline-Bis Triazine (C1-BTPhen) on Magnetic Nanoparticles for Co-Extraction of Americium(III) and Europium(III)

  摘要：

  The present work reports a convenient route for the immobilisation of a phenanthroline-bis triazine (C1-BTPhen) group on the surface of zirconia-coated maghemite (gamma-Fe2O3) magnetic nanoparticles. The magnetic nanoparticles functionalized with C1-BTPhen were able to co-extract Am(III) and Eu(III) from nitric acid (HNO3). The extraction efficiency of these C1-BTPhen-functionalized magnetic nanoparticles for both Am(III) and Eu(III) was 20% at 4M HNO3. The interaction between C1-BTPhen and metal cations is reversible. These functionalized magnetic nanoparticles can be used for the co-extraction of traces of Am(III) and Eu(III).

  DOI：

  10.3987/com-13-s(s)9
• 作为产物：
  描述：

  5-bromo-2,9-dimethyl-1,10-phenanthroline 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.5h， 以62%的产率得到5-bromo-1,10-phenanthroline-2,9-dicarbaldehyde
  参考文献：
  名称：

  走向 A,D-(1,10-菲咯啉)-桥接杯[6]芳烃树枝状聚合物

  摘要：

  5-溴-2,9-双（溴甲基）-1,10-菲咯啉（5）已从 5-溴-2,9-二甲基-1,10-菲咯啉（1）开始合成，总产率高达53% 通过两种方法。接下来，杯 [6] 芳烃 (7) 与 5 桥连，以 42% 的产率得到 A,D 桥连的双大环 9。在 Sonogashira 反应条件的应用下，三甲基甲硅烷基保护的乙炔首先偶联到 1,10-菲咯啉的 5-位，然后乙炔单元脱保护并与 1,3,5-三碘苯 (12) 作为三价连接核。形成了三聚体第一代树枝状聚合物 13，连同 Glaser 二聚体副产物，并且可以以 36% 的产率分离。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  DOI：

  10.1002/ejoc.200700639

文献信息

• Utilizing electronic effects in the modulation of BTPhen ligands with respect to the partitioning of minor actinides from lanthanides
  作者：Ashfaq Afsar、Dominic M. Laventine、Laurence M. Harwood、Michael J. Hudson、Andreas Geist

  DOI：10.1039/c3cc45126g

  日期：——

  Effects of bromine substitution at the 5 and 5,6-positions of the 1,10-phenanthroline nucleus of BTPhen ligand on their extraction properties for Ln(III) and An(III) cations have been studied. Compared to C5-BTPhen, electronic modulation in BrC5-BTPhen and Br2C5-BTPhen enabled these ligands to be fine-tuned in order to enhance the separation selectivity of Am(III) from Eu(III).

  研究了 BTPhen 配体的 1,10-菲罗啉核的 5 和 5,6 位溴取代对其萃取 Ln(III) 和 An(III) 阳离子特性的影响。与 C5-BTPhen 相比，BrC5-BTPhen 和 Br2C5-BTPhen 中的电子调制使这些配体能够进行微调，以提高 Am(III) 与 Eu(III) 的分离选择性。
• Towards A,D-(1,10-Phenanthroline)-Bridged Calix[6]arene Dendrimers
  作者：Jan P. W. Eggert、Ulrich Lüning

  DOI：10.1002/ejoc.200700639

  日期：2007.12

  approaches. Next, calix[6]arene (7) was bridged with 5, giving the A,D-bridged bimacrocyle 9 in 42 % yield. Under application of Sonogashira reaction conditions, trimethylsilyl-protected ethyne was first coupled to the 5-position of the 1,10-phenanthroline, and the ethyne unit was then deprotected and connected with 1,3,5-triiodobenzene (12) as a trivalent core. A trimeric first-generation dendrimer 13 was formed

  5-溴-2,9-双（溴甲基）-1,10-菲咯啉（5）已从 5-溴-2,9-二甲基-1,10-菲咯啉（1）开始合成，总产率高达53% 通过两种方法。接下来，杯 [6] 芳烃 (7) 与 5 桥连，以 42% 的产率得到 A,D 桥连的双大环 9。在 Sonogashira 反应条件的应用下，三甲基甲硅烷基保护的乙炔首先偶联到 1,10-菲咯啉的 5-位，然后乙炔单元脱保护并与 1,3,5-三碘苯 (12) 作为三价连接核。形成了三聚体第一代树枝状聚合物 13，连同 Glaser 二聚体副产物，并且可以以 36% 的产率分离。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Comparing the Extraction of Am(III), Cm(III) and Eu(III) by CyMe4-BTPhen-Functionalized Silica and Zirconia-Coated Magnetic Nanoparticles
  作者：Laurence M. Harwood、Ashfaq Afsar、James Westwood、Michael J. Hudson、Jan John、Petr Distler

  DOI：10.3987/com-15-s(t)58

  日期：——

  Herein, we report the synthesis of CyMe4-BTPhen-functionalized zirconia-coated (ZrO2) maghemite (gamma-Fe2O3) magnetic nanoparticles (MNPs) and their ability to extract Am(III) from Eu(III) and Am(III) from Cm(III) in a range of HNO3 concentrations (0.001 - 4 M). Their extraction behavior is compared to our previously tested model based on silica-coated (SiO2) MNPs. Extraction of Am(III) and Eu(III) is reported, but little or no selectivity can be seen between Am(III) and Cm(III) at concentrations of 4 M HNO3.
• Effective Separation of Am(III) from Cm(III) Using Modified BTPhen Ligands
  作者：Laurence M. Harwood、Ashfaq Afsar、Alyn C. Edwards、Andreas Geist、Michael J. Hudson、James Westwood、Roger C. Whitehead

  DOI：10.3987/com-16-s(s)26

  日期：——

  Electronic modulation of CyMe4-BTPhen with 5-bromo and 5-(4-hydroxyphenyl) substituents leads to enhanced separation of Am(III) from Cm(III) over 0.1 - 3 M HNO3 (SFAm/Cm = ca. 9 at 0.1 M HNO3). In addition, substituting bromine atoms at the 5 and 6 positions of the phenanthroline backbone provides a mean of separating Am(III) from Eu(III) (SFAm/Eu = ca. 240 at 3 M HNO3).
• Immobilisation of Phenanthroline-Bis Triazine (C1-BTPhen) on Magnetic Nanoparticles for Co-Extraction of Americium(III) and Europium(III)
  作者：Laurence M. Harwood、Ashfaq Afsar、Dominic L. Laventine、Michael J. Hudson、Andreas Geist

  DOI：10.3987/com-13-s(s)9

  日期：——

  The present work reports a convenient route for the immobilisation of a phenanthroline-bis triazine (C1-BTPhen) group on the surface of zirconia-coated maghemite (gamma-Fe2O3) magnetic nanoparticles. The magnetic nanoparticles functionalized with C1-BTPhen were able to co-extract Am(III) and Eu(III) from nitric acid (HNO3). The extraction efficiency of these C1-BTPhen-functionalized magnetic nanoparticles for both Am(III) and Eu(III) was 20% at 4M HNO3. The interaction between C1-BTPhen and metal cations is reversible. These functionalized magnetic nanoparticles can be used for the co-extraction of traces of Am(III) and Eu(III).