2-(2,5-dimethylthiophen-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | 942070-20-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2-(2,5-dimethylthiophen-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 942070-20-4
• 化学式: C₁₂H₁₉BO₂S
• 分子量: 238.159
• InChiKey: QGOMTDDALYCQMG-UHFFFAOYSA-N

物化性质

• 沸点：
  324.4±42.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H312,H315,H319,H332,H335
• 储存条件：
  -20°C，密封保存，置于干燥处。

SDS

MSDS英文版

反应信息

• 作为反应物：
  描述：

  2-(2,5-dimethylthiophen-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 在 四(三苯基膦)钯 、 正丁基锂 、 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 生成 2,3-bis(2,5-dimethylthiophen-3-yl)-5-iodothiophene
  参考文献：
  名称：

  具有三键桥的三角三噻吩和羟苯基苯并噻唑构型荧光染料的研究

  摘要：

  通过结合碳-碳三键间隔三角形三联噻吩骨架和羟基苯基苯并噻唑构建了一种光致变色染料。用交替的紫外线 (254 nm) 和可见光 (≥ 400 nm) 照射研究了常规的光致变色行为。溶液中染料的颜色可以在粉红色和无色之间循环。此外，染料溶液在 THF 中发出强烈荧光，绝对量子产率 (QY) 为 0.56。当用254 nm的光照射时，发射溶液可以有效地猝灭到光静止状态（Φ = 0.05）。可以根据紫外线/可见光照射周期建立发射“开-关”周期。光致变色染料在室温下也表现出良好的光稳定性和热稳定性。发射衰减曲线表明典型的单组分特征，荧光寿命为 6.68 ns。发射颜色由蓝色区域中x  = 0.14、y  = 0.25 的 CIE 1931 坐标确定。

  DOI：

  10.1007/s10895-022-03049-3
• 作为产物：
  描述：

  2,5-二甲基噻吩 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 2-(2,5-dimethylthiophen-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  The excited-state intramolecular proton transfer fluorescence of HBT derivative induced by solvent polarity

  摘要：

  In this contribution, a dye (THBT) with 2,5-dimethylthiophene substituted to 2-(2-hydroxyphenyl)benzothiazole was synthesized and characterized by NMR and mass spectroscopic techniques. Its emission behavior in various solvents was investigated and obvious negative solvatochromism was observed. The emission maximum of THBT varied from deep blue (425nm) in DMSO to orange (550nm) in chloroform. It is also highly emissive in polycarbonate film and solid powder with the emission peaks 546 and 554nm, respectively. The ESIPT effect, together with the relaxation of free rotation of thiophene in the excited states, shifted the solid emission 34nm toward longer wavelength furtherly, with respect the 520nm (green) emission of HBT. Quantum calculation of frontier molecular orbitals uncovers the underlying mechanism of negative solvatochromism.

  DOI：

  10.1080/15421406.2016.1200923

文献信息

• Microwave-Accelerated Iridium-Catalyzed Borylation of Aromatic C−H Bonds
  作者：Peter Harrisson、James Morris、Todd B. Marder、Patrick G. Steel

  DOI：10.1021/ol901306m

  日期：2009.8.20

  accelerates the Ir-catalyzed C−H borylation of aromatic substrates when compared with reactions carried out at the same temperature under standard heating conditions. Application to a one-pot single solvent process for tandem C−H borylation/Suzuki−Miyaura cross-coupling sequences using microwave-accelerated reactions gives fast and efficient access to a wide range of biaryl and heterobiaryl compounds.

  与在标准加热条件下在相同温度下进行的反应相比，微波加热可加速芳族底物的Ir催化CH硼化。通过微波加速反应应用于串联C–H硼酸酯化/ Suzuki-Miyaura交叉偶联序列的一锅单一溶剂工艺，可以快速，有效地获得各种联芳基和杂联芳基化合物。
• Sterically Controlled Alkylation of Arenes through Iridium-Catalyzed CH Borylation
  作者：Daniel W. Robbins、John F. Hartwig

  DOI：10.1002/anie.201208203

  日期：2013.1.14

  one‐pot method for the site‐selective alkylation of arenes controlled by steric effects is reported. The process occurs through Ir‐catalyzed CH borylation, followed by Pd‐ or Ni‐catalyzed coupling with alkyl electrophiles. This selectivity complements that of the typical Friedel–Crafts alkylation; meta‐selective alkylation of a broad range of arenes with various electronic properties and functional

  互补化学：报道了一种通过空间效应控制芳烃的位点选择性烷基化的单锅法。发生的过程通过铱催化的Ç  ħ硼基化，随后Pd或Ni基催化的亲电子烷基偶联。这种选择性补充了典型的Friedel-Crafts烷基化反应的选择性。元的宽范围的各种电子性质和官能团的芳烃-选择性的烷基化发生在良好的产率与部位选择性高。
• A New Synthetic Pathway to Symmetric Bisubstituted Naphthoquinones
  作者：Vasily A. Migulin

  DOI：10.1055/s-0039-1690725

  日期：2020.1

  straightforward and practical synthesis of 2,3-diiodo-1,4-naphthoquinone is reported. Based on the prepared diiodide, a new synthetic approach to symmetric bisubstituted 1,4-naphthoquinones via double Suzuki–Miyaura reaction at room temperature has been researched and developed. The presented general method combines broad-spectrum applicability, efficiency, and simplicity providing target materials

  报道了直接和实用的2，3-二碘-1，4-萘醌的合成。在制备的二碘化物的基础上，研究和开发了一种在室温下通过双铃木-宫浦双反应合成对称的双取代的1,4-萘醌的新方法。提出的通用方法结合了广谱的适用性，效率和简便性，以良好的定量产量提供了目标物质。
• Pendant Photochromic Conjugated Polymers Incorporating a Highly Functionalizable Thieno[3,4-<i>b</i>]thiophene Switching Motif
  作者：Garvin M. Peters、John D. Tovar

  DOI：10.1021/jacs.8b12617

  日期：2019.2.20

  chain to allow for electronic influence along the polymer backbone while avoiding substantial conformational demands that may affect solid-state performance. Herein, we report the synthesis of a series of thieno[3,4- b]thiophene (TT)-based photochromes that demonstrate drastically different optoelectronic properties upon cyclization. Experimental and computational investigations of aryl-extended model

  外部调制共轭聚合物光电特性的能力是现代有机电子产品的重要挑战。一种有吸引力的方法是将刺激响应分子系统（例如二芳基乙烯）结合到聚合物材料中。我们的方法涉及设计具有悬挂在主共轭链上的光致变色部分的聚合物，以允许沿聚合物主链的电子影响，同时避免可能影响固态性能的大量构象需求。在此，我们报告了一系列基于噻吩并 [3,4-b] 噻吩 (TT) 的光致变色材料的合成，它们在环化时表现出截然不同的光电特性。
• Iridium-catalyzed borylation of thiophenes: versatile, synthetic elaboration founded on selective C–H functionalization
  作者：Ghayoor A. Chotana、Venkata A. Kallepalli、Robert E. Maleczka、Milton R. Smith

  DOI：10.1016/j.tet.2008.02.111

  日期：2008.6

  various substituted thiophenes to synthesize poly-functionalized thiophenes in good to excellent yields. Apart from common functionalities compatible with iridium-catalyzed borylations, additional functional group tolerance to acyl (COMe), and trimethylsilyl (TMS) groups was also observed. High regioselectivities were observed in borylation of 3-and 2,5-di-substituted thiophenes. Electrophilic aromatic

  铱催化的硼酸化反应已应用于各种取代的噻吩以合成多官能化的噻吩，收率非常好。除了与铱催化的硼化反应兼容的常见官能团外，还观察到了对酰基 (COMe) 和三甲基甲硅烷基 (TMS) 基团的额外官能团耐受性。在 3-和 2,5-二取代噻吩的硼酸化中观察到高区域选择性。噻吩硼酸酯上的亲电芳族 CH/C-Si 溴化显示在不破坏 CB 键的情况下发生，并且一锅 CH 硼酸化/Suzuki-Miyaura 交叉偶联已在 2-和 3-硼酸化噻吩上完成。