25-二氟-14-亚苯基二硼酸 | 1256358-83-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 25-二氟-14-亚苯基二硼酸
• 中文别名: 2,5-二氟-1,4-苯二酸
• 英文名称: 2,5-difluoro-1,4-phenyleneboronic acid
• 英文别名: (2,5-difluoro-1,4-phenylene)diboronic acid；2,5-difluoro-1,4-benzenediboronic acid；2,5-difluoroterephthalenediboronic acid；(4-borono-2,5-difluorophenyl)boronic acid
• CAS: 1256358-83-4
• 化学式: C₆H₆B₂F₂O₄
• 分子量: 201.73
• InChiKey: CSOLBHLZNAGMMP-UHFFFAOYSA-N

物化性质

• 沸点：
  419.3±55.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.68
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  6

安全信息

• 海关编码：
  2916399090
• 危险性防范说明：
  P233,P260,P261,P264,P270,P271,P280,P301+P312,P302+P352,P304,P304+P340,P305+P351+P338,P312,P321,P330,P332+P313,P337+P313,P340,P362,P403,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

SDS

2,5-二氟-1,4-苯二硼酸MSDS英文版

反应信息

• 作为反应物：
  描述：

  25-二氟-14-亚苯基二硼酸 、 以 氘代氯仿 为溶剂， 反应 4.0h， 以84%的产率得到
  参考文献：
  名称：

  形状持久的四面体[4 + 6]硼酸酯笼，具有不同的氟取代度

  摘要：

  近年来，通过动态共价化学（DCC）合成的形状持久性有机笼状化合物的兴趣日益浓厚，因为这些笼状结构对于气体吸附或分离具有潜在的意义。DCC中的一种这样的反应是硼酸与二醇的缩合以形成硼酸酯。最有趣的是，硼酸酯笼子的几何形状和尺寸比例如基于亚胺的笼子低得多。在这里，介绍了一系列形状持久的[4 + 6]四面体硼酸酯笼。一个笼子具有511 m 2  g -1的高比表面积，并选择性地将乙烷吸附在乙烯和乙炔上。

  DOI：

  10.1002/chem.201802123
• 作为产物：
  描述：

  1,4-二溴-2,5-二氟苯 在 正丁基锂 、 硼酸三异丙酯 、 硫酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 生成 25-二氟-14-亚苯基二硼酸
  参考文献：
  名称：

  Structural and Energetic Landscape of Fluorinated 1,4-Phenylenediboronic Acids

  摘要：

  The results of X-ray crystallographic and computational studies of a series of fluorinated 1,4-phenylenediboronic acids (i.e., fluoro-1,4-phenylenediboronic acid, 2,6-difluoro-1,4-phenylenediboronic acid, 2,3-difluoro-1,4-phenylenediboronic acid, 2,5-difluoro-1,4-phenylenediboronic acid, and tetrafluoro-1,4-phenylenediboronic acid) are reported. The effect of fluorine substitution on crystal organization in the presence of strong and directional hydrogen bonds was studied. Comparison with the two previously reported forms of the unsubstituted 1,4-phenylenediboronic acid revealed a strong relation between a supramolecular network and the number of water molecules present in the crystal lattice. As indicated by the theoretical calculations performed in the CRYSTAL and PIXEL programs, the structures with greater amount of water are better stabilized (from about -170 kJ.mol(-1) for anhydrous forms to about -420 kJ.mol(-1) for tetrahydrate). The energy of hydrogen bonded dimers vary from -40 kJ.mol(-1) to -50 kJ.mol(-1). Contacts with fluorine atoms play rather a secondary role in the crystal packing. Fluorine substituents tend to interact with the electropositive boron atom. Furthermore, intramolecular interactions significantly affect the torsion angle of the B(OH)(2) group. The constrained energy scan revealed that stronger interactions with substituents stabilize the planar conformation and hamper the rotation of the boronic group. This in turn has a further impact on the interactions within selected crystal motifs and supposedly rules the proton disorder within boronic fragments. Besides the interactions with the fluorine atoms, other weak contacts such as C(pi)center dot center dot center dot B and O center dot center dot center dot B also influence the molecular organization. The energy of the corresponding dimers varies from -15 kJ.mol(-1) to -25 kJ.mol(-1).

  DOI：

  10.1021/cg3005272

文献信息

• Release and Recovery of Guest Molecules during the Reversible Borate Gel Formation of Guest-Included Macrocyclic Boronic Esters
  作者：Suguru Ito、Hisatsugu Takata、Kosuke Ono、Nobuharu Iwasawa

  DOI：10.1002/anie.201303870

  日期：2013.10.11

  Borate gel formation from guest‐encapsulated macrocyclic boronic esters was realized by the addition of a diamine to the suspension of the boronic esters in various organic solvents, which triggered the release of the guest compounds. The guest molecules could be recovered from the borate gel by addition of an acid to remove the diamine, which facilitated the reconstruction of the initial guest‐encapsulated

  通过将二胺添加到硼酸酯在各种有机溶剂中的悬浮液中，实现了由客体封装的大环硼酸酯形成硼酸盐凝胶，从而触发了客体化合物的释放。客体分子可通过添加酸以去除二胺而从硼酸盐凝胶中回收，这有利于初始客体包封的大环硼酸酯的重建。
• Thermochromic Afterglow from Benzene‐1,4‐Diboronic Acid‐Doped Co‐crystals
  作者：Kaede Kawaguchi、Natsumi Sugawara、Masato Ito、Yuji Kubo

  DOI：10.1002/chem.202303924

  日期：2024.3.7

  The accurate thermosensing requires a minimum impact of autofluorescence and light scattering from the samples. In this study, we discovered that commercially available benzene‐1,4‐diboronic acid (BDBA) doped co‐crystals with trimethylolpropane (TMP) exhibit excellent thermochromic dual phosphorescence properties over a wide temperature range from −132 to 40 °C, despite its simple structure that does not have any donor‐acceptor linkage. The dual phosphorescence was consisted of monomeric benzene‐1,4‐diboronate (BDBA ester) and aggregation‐stabilized species. With an increase in temperature, the emission intensity from the monomeric state significantly decreased, whereas that originating from the aggregated state remained almost constant owing to the difference in their thermal stabilities. Further investigation revealed that molecular distortions in singlet excited states enable efficient intersystem crossing, causing efficient phosphorescence from the monomeric state of BDBA ester.

  摘要准确的热感应需要将样品的自发荧光和光散射影响降至最低。在这项研究中，我们发现市售的掺杂了三羟甲基丙烷（TMP）的苯-1,4-二硼酸（BDBA）共晶体尽管结构简单，没有任何供体-受体连接，但在-132 至 40 ℃的宽温度范围内表现出优异的热致变色双磷光特性。双磷光由单体苯-1,4-二硼酸酯（BDBA 酯）和聚集稳定的物种组成。随着温度的升高，单体状态的发射强度明显降低，而聚集状态的发射强度几乎保持不变，这是因为它们的热稳定性不同。进一步的研究表明，单子激发态的分子畸变能够实现有效的系统间交叉，从而使 BDBA 酯的单体态产生有效的磷光。
• 一种由三联吡啶片段组装而成的具有聚集诱导电致化学发光的纯有机发光体及其合成方法
  申请人：桂林理工大学

  公开号：CN117567368A

  公开（公告）日：2024-02-20

  本发明公开一种由三联吡啶片段组装而成的具有聚集诱导电致化学发光的纯有机发光体及其合成方法，化学结构式为：#imgabs0#。所述的纯有机发光体I和II一种是利用二醛取代基化合物、2‑乙酰吡啶与氨水在叔丁醇钾的作用下合成了由三联吡啶片段组装而成的纯有机发光体。所述的纯有机发光体I和II另一种是以硼酸或硼酯取代化合物和卤素取代化合物在钯催化剂、无机碱的作用下合成了由三联吡啶片段组装而成的纯有机发光体。所述的纯有机发光体III是利用过氧化物氧化所述纯有机发光体I合成了由三联吡啶片段组装而成的纯有机发光体。本发明的纯有机发光体具有强的聚集诱导电致化学发光，可应用于传感器、有机发光半导体等领域，应用前景广泛。
• Shape-Persistent Tetrahedral [4+6] Boronic Ester Cages with Different Degrees of Fluoride Substitution
  作者：Sven M. Elbert、Nicolas I. Regenauer、Dorothee Schindler、Wen-Shan Zhang、Frank Rominger、Rasmus R. Schröder、Michael Mastalerz

  DOI：10.1002/chem.201802123

  日期：2018.8.6

  shape‐persistent organic cage compounds synthesized by dynamic covalent chemistry (DCC) has risen, because these cages are potentially interesting for gas sorption or ‐separation. One such reaction in DCC is the condensation of boronic acids with diols to form boronic esters. Most interestingly, the variety of geometries and sizes for boronic ester cages is much lower than that of, for example, imine‐based cages

  近年来，通过动态共价化学（DCC）合成的形状持久性有机笼状化合物的兴趣日益浓厚，因为这些笼状结构对于气体吸附或分离具有潜在的意义。DCC中的一种这样的反应是硼酸与二醇的缩合以形成硼酸酯。最有趣的是，硼酸酯笼子的几何形状和尺寸比例如基于亚胺的笼子低得多。在这里，介绍了一系列形状持久的[4 + 6]四面体硼酸酯笼。一个笼子具有511 m 2  g -1的高比表面积，并选择性地将乙烷吸附在乙烯和乙炔上。
• Structural and Energetic Landscape of Fluorinated 1,4-Phenylenediboronic Acids
  作者：Krzysztof Durka、Katarzyna N. Jarzembska、Radosław Kamiński、Sergiusz Luliński、Janusz Serwatowski、Krzysztof Woźniak

  DOI：10.1021/cg3005272

  日期：2012.7.3

  The results of X-ray crystallographic and computational studies of a series of fluorinated 1,4-phenylenediboronic acids (i.e., fluoro-1,4-phenylenediboronic acid, 2,6-difluoro-1,4-phenylenediboronic acid, 2,3-difluoro-1,4-phenylenediboronic acid, 2,5-difluoro-1,4-phenylenediboronic acid, and tetrafluoro-1,4-phenylenediboronic acid) are reported. The effect of fluorine substitution on crystal organization in the presence of strong and directional hydrogen bonds was studied. Comparison with the two previously reported forms of the unsubstituted 1,4-phenylenediboronic acid revealed a strong relation between a supramolecular network and the number of water molecules present in the crystal lattice. As indicated by the theoretical calculations performed in the CRYSTAL and PIXEL programs, the structures with greater amount of water are better stabilized (from about -170 kJ.mol(-1) for anhydrous forms to about -420 kJ.mol(-1) for tetrahydrate). The energy of hydrogen bonded dimers vary from -40 kJ.mol(-1) to -50 kJ.mol(-1). Contacts with fluorine atoms play rather a secondary role in the crystal packing. Fluorine substituents tend to interact with the electropositive boron atom. Furthermore, intramolecular interactions significantly affect the torsion angle of the B(OH)(2) group. The constrained energy scan revealed that stronger interactions with substituents stabilize the planar conformation and hamper the rotation of the boronic group. This in turn has a further impact on the interactions within selected crystal motifs and supposedly rules the proton disorder within boronic fragments. Besides the interactions with the fluorine atoms, other weak contacts such as C(pi)center dot center dot center dot B and O center dot center dot center dot B also influence the molecular organization. The energy of the corresponding dimers varies from -15 kJ.mol(-1) to -25 kJ.mol(-1).