(4-溴苯基硫代)二甲基叔丁基硅烷 | 153312-70-0

• 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: (4-溴苯基硫代)二甲基叔丁基硅烷
• 中文别名: (4-溴苯基硫代)二甲基-叔丁基硅烷
• 英文名称: (4-bromophenylthio)-dimethyl-tert-butyl-silane
• 英文别名: (4-bromophenylsulfanyl)-tert-butyldimethylsilane；(4-Bromophenylthio)dimethyl-tert-butylsilane；(4-bromophenyl)sulfanyl-tert-butyl-dimethylsilane
• CAS: 153312-70-0
• 化学式: C₁₂H₁₉BrSSi
• 分子量: 303.338
• InChiKey: ZVSDFKXSTADQGI-UHFFFAOYSA-N

物化性质

• 熔点：
  42-44 °C(lit.)
• 沸点：
  120-130 °C0.2-0.3 mm Hg(lit.)
• 密度：
  1.20±0.1 g/cm3(Predicted)
• 闪点：
  >230 °F
• 稳定性/保质期：
  在常温常压下保持稳定，应避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  5.55
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 安全说明：
  S26

反应信息

• 作为反应物：
  描述：

  (4-溴苯基硫代)二甲基叔丁基硅烷 在 正丁基锂 、 potassium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 4.25h， 生成 4-甲硫基苯硼酸
  参考文献：
  名称：

  Boronated thiophenols: a preparation of 4-mercaptophenylboronic acid and derivatives

  摘要：

  4-Mercaptophenylboronic acid derivatives were prepared by a metallation/boration sequence from S-protected 3-bromothiophenols; the t-butyldimethylsilylthioether was found suitable to allow subsequent regeneration of the mercapto group after boration. The parent compound, 4-mercaptophenylboronic acid, could thus be obtained and was subsequently S-alkylated; 4-boronophenylthioacetic acid was prepared without the need to protect the boronic acid group. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(99)00086-8
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 4-溴苯硫酚 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以92%的产率得到(4-溴苯基硫代)二甲基叔丁基硅烷
  参考文献：
  名称：

  Boronated thiophenols: a preparation of 4-mercaptophenylboronic acid and derivatives

  摘要：

  4-Mercaptophenylboronic acid derivatives were prepared by a metallation/boration sequence from S-protected 3-bromothiophenols; the t-butyldimethylsilylthioether was found suitable to allow subsequent regeneration of the mercapto group after boration. The parent compound, 4-mercaptophenylboronic acid, could thus be obtained and was subsequently S-alkylated; 4-boronophenylthioacetic acid was prepared without the need to protect the boronic acid group. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(99)00086-8

文献信息

• GlucoSiFA and LactoSiFA: New Types of Carbohydrate-Tagged Silicon-Based Fluoride Acceptors for 18F-Positron Emission Tomography (PET)
  作者：Anja Wiegand、Vera Wiese、Britta Glowacki、Ljuba Iovkova、Ralf Schirrmacher、Klaus Jurkschat、Norbert Krause

  DOI：10.1055/s-0037-1611656

  日期：2019.3

  GlucoSiFA derivatives bearing an azide or alkynyl side chain were obtained from peracetyl-d-glucose using as key step a tosylate substitution by a SiFA thiolate obtained from 4-(di-tert-butylfluorsilyl)benzenethiol. In analogy, two-fold SiFA-substituted maltose and lactose derivatives were synthesized via bistosylates. Introduction of an ­acetal-protecting group in β-d-azidolactose allowed the synthesis of a LactoSiFA derivative bearing only one SiFA moiety.

  从过醋酸乙酰-D-葡萄糖中获得带有偶氮或炔基侧链的GlucoSiFA衍生物，其中关键步骤是通过从4-(二-叔丁基氟硅基)苯硫醇获得的SiFA硫醇酯对甙基进行磺酸酯取代。类似地，通过双磺酸酯合成了双SiFA取代的麦芽糖和乳糖衍生物。在β-D-偶氮乳糖中引入缩醛保护基允许合成只带有一个SiFA基团的LactoSiFA衍生物。
• <i>para</i>-Functionalized Aryl-di-<i>tert</i>-butylfluorosilanes as Potential Labeling Synthons for¹⁸F Radiopharmaceuticals
  作者：Ljuba Iovkova、Björn Wängler、Esther Schirrmacher、Ralf Schirrmacher、Gabriele Quandt、Guido Boening、Markus Schürmann、Klaus Jurkschat

  DOI：10.1002/chem.200802266

  日期：2009.2.16

  es, p‐(tBu2FSi)C6H4X (X=functional group), have been made available and broaden the spectrum of silicon‐based 18F acceptors (SiFAs) for potential PET applications. For example, the [18F]maleimido derivative 1 has been employed for the synthesis of [18F]1‐ labeled rat serum albumin (RSA), the applicability of which for PET has been verified by in vivo experiments.

  广谱：新型对位官能化的芳基-二叔丁基氟硅烷p-（t Bu 2 FSi）C 6 H 4 X（X =官能团）已经面世，并拓宽了硅基18 F受体的范围（SiFA）用于潜在的PET应用。例如，[ 18 F]马来酰亚胺衍生物1已用于[ 18 F] 1-标记的大鼠血清白蛋白（RSA）的合成，其在PET中的适用性已通过体内实验得到验证。
• Boron‐Centered Lewis Superacid through Redox‐Active Ligands: Application in C−F and S−F Bond Activation
  作者：Laura Köring、Arne Stepen、Bernhard Birenheide、Simon Barth、Maxim Leskov、Roland Schoch、Felix Krämer、Frank Breher、Jan Paradies

  DOI：10.1002/anie.202216959

  日期：2023.3.20

  synthesis of strong boron-centered Lewis superacids. The Lewis superacids were characterized by NMR, XRD and FIA computation. The ferrocenium-substituted boranes were applied in catalytic C−F and S−F bond activations.

  二茂铁取代的硼烷和硼酸酯的氧化可以直接合成以硼为中心的强路易斯超强酸。路易斯超强酸通过 NMR、XRD 和 FIA 计算来表征。二茂铁取代的硼烷用于催化 C-F 和 S-F 键活化。
• Boronated thiophenols: a preparation of 4-mercaptophenylboronic acid and derivatives
  作者：Abdelghani Brikh、Christophe Morin

  DOI：10.1016/s0022-328x(99)00086-8

  日期：1999.6

  4-Mercaptophenylboronic acid derivatives were prepared by a metallation/boration sequence from S-protected 3-bromothiophenols; the t-butyldimethylsilylthioether was found suitable to allow subsequent regeneration of the mercapto group after boration. The parent compound, 4-mercaptophenylboronic acid, could thus be obtained and was subsequently S-alkylated; 4-boronophenylthioacetic acid was prepared without the need to protect the boronic acid group. (C) 1999 Elsevier Science S.A. All rights reserved.