TEMPO甲基丙烯酸酯 | 15051-46-4

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: TEMPO甲基丙烯酸酯
• 中文别名: 4-甲基丙烯酰氧-2,2,6,6-四甲基哌啶1-氧自由基；PTMA单体；4-甲基丙烯酰氧-TEMPO自由基；TEMPO甲基丙烯酸甲酯
• 英文名称: 4-methacryloxy-2,2,6,6-tetramethyl-1-piperidinyloxyl
• 英文别名: 4-methacryloyloxy-2,2,6,6-tetramethylpiperidin-1-oxyl；4-methacryloyloxy-2,2,6,6-tetramethylpiperidinyloxy；4-Methacryloyloxy-2,2,6,6-tetramethylpiperidine-1-oxyl；4-Methacryloyloxy-2,2,6,6-tetramethyl-piperidin-1-oxid
• CAS: 15051-46-4
• 化学式: C₁₃H₂₂NO₃
• 分子量: 240.323
• InChiKey: BTWSPOZXDCFMLX-UHFFFAOYSA-N

物化性质

• 熔点：
  87.0 to 91.0 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  30.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• WGK Germany：
  1
• 危险性防范说明：
  P280
• 危险性描述：
  H317

反应信息

• 作为反应物：
  描述：

  TEMPO甲基丙烯酸酯 在 hexafluorophosphoric acid 、 sodium hypochlorite 作用下， 以 水 为溶剂， 反应 4.0h， 以5.4%的产率得到4-methacryloyl-1-oxo-2,2,6,6-tetramethylpiperidinium hexafluorophosphate
  参考文献：
  名称：

  Synthesis of Poly(oxoammonium salt)s and Their Electrical Properties in the Organic Thin Film Device

  摘要：

  我们分别通过 TEMPO 取代聚合物的化学氧化法或草铵单体的传统自由基聚合法合成了两种氧化还原活性聚（草铵盐）。与不含自由基的聚氧化铵盐相比，自由基浓度为 6-43% 的聚氧化铵盐组成的二极管结构薄膜器件表现出电阻开关行为（导通-关断比 >103），这表明自由基/氧化铵盐的共存导致了 I-V 特性的显著变化。

  DOI：

  10.1246/cl.2009.1160
• 作为产物：
  描述：

  阻聚剂701 、 甲基丙烯酸酐 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 13.5h， 以90%的产率得到TEMPO甲基丙烯酸酯
  参考文献：
  名称：

  Strategies for the Generation of Molecularly Imprinted Polymeric Nitroxide Catalysts

  摘要：

  [GRAPHICS]Two strategies for preparing catalytically active molecularly imprinted nitroxide-containing polymers are outlined. Both strategies rely upon the thermal rearrangement chemistry of tertiary amine N-oxides. To this end, several polymers were prepared and the polymeric nitroxides were revealed by oxidation with m-CPBA. All of the resulting polymeric catalysts proved to be competent mediators of the oxidation of alcohols.

  DOI：

  10.1021/ol051749n

文献信息

• Functional Nitroxyls for Use in Delayed-Onset Polyolefin Cross-Linking
  作者：David K. Hyslop、J. Scott Parent

  DOI：10.1021/ma3016135

  日期：2012.10.23

  macroradicals in the early stages of the process and to subsequently generate a covalent network through the oligomerization of polymer-bound acrylate functionality. Selectivity of alkyl radical trapping by AOTEMPO to give alkoxyamine intermediates in preference to acrylate addition products is discovered using model compound studies and through rheological measurements of linear low density polyethylene

  描述了控制聚烯烃自由基交联的动力学和产率的新方法，其中4-丙烯酰氧基-2,2,6,6-四甲基哌啶-N-oxyl（AOTEMPO）用于在该方法的早期阶段淬灭大自由基，并随后通过与聚合物结合的丙烯酸酯官能团的低聚反应生成共价网络。使用模型化合物研究和通过线性低密度聚乙烯交联的流变测量，发现了由AOTEMPO捕获烷基自由基以优先于丙烯酸酯加成产物生成烷基氧基胺中间体的选择性。后者证明了AOTEMPO能够延迟交联的开始，同时又不影响所得热固性材料的交联密度。定量和讨论了试剂用量，过氧化物分解速率和可聚合官能团结构的影响。
• TW2018/40535
  申请人：——

  公开号：——

  公开（公告）日：——
• Battery-Inspired, Nonvolatile, and Rewritable Memory Architecture:  a Radical Polymer-Based Organic Device
  作者：Yasunori Yonekuta、Kentaro Susuki、Kenichi Oyaizu、Kenji Honda、Hiroyuki Nishide*

  DOI：10.1021/ja075553p

  日期：2007.11.1

  A nonvolatile, bistable, and rewritable organic memory device based on radical polymers was prepared and tested. The excellent performance of a battery-inspired memory architecture with a configuration of p- and n-type charge-transporting radical polymers sandwiching a dielectric layer was characterized. The ON-OFF ratio was more than 4 orders of magnitude, and retention and endurance cycles of more than 10(4) and 10(3), respectively, were accomplished.
• Tacticity Influence on the Electrochemical Reactivity of Group Transfer Polymerization-Synthesized PTMA
  作者：Hugo A. López-Peña、Lindsay S. Hernández-Muñoz、Bernardo A. Frontana-Uribe、Felipe J. González、Ignacio González、Carlos Frontana、Judith Cardoso

  DOI：10.1021/jp301207v

  日期：2012.5.10

  Spectroscopic, thermal, and electrochemical characterization results are presented for the redox active polymer poly(2,2,6,6-tetramethyl-1-piperinidyloxy-4-yl methacrylate) or PTMA, synthesized by group transfer polymerization (GTP), and its precursors 4-hydroxy-tetramethylpiperidine-N-oxyl (HO-TEMPO) and 4-methacryloyloxy-tetramethylpiperidine-N-oxyl (MO-TEMPO). DSC analysis of synthesized PTMA showed that the glass transition temperature (T-g) of the polymer structure occurs at 155 degrees C, corroborated by dynamic mechanical analysis (DMA), which is higher when compared with T-g data for PTMA synthesized by other methods. Also, the amount of radical species present in PTMA synthesized by GTP reactions (100%) is higher than the values typically upon synthesizing PTMA by radical polymerization. Electrochemical and spectroelectrochemical-electron spin resonance studies in acetonitrile revealed two redox events in the PTMA polymer, one of which is reversible, accounting for ca. 80% of the spins in the polymer and giving rise to the battery behavior. The other redox event is irreversible, accounting for the remaining ca. 20% of spins, which has not previously been reported. These two redox events are linked to a structural property associated with the tacticity of the polymer, where the reversible feature (responsible for cathode behavior) is the dominant species. This corresponds to a number of isotactic domains of the polymer (determined by high temperature H-1 NMR). The second feature accounts for the three-line impurity observed in the ESR, which has been reported previously but poorly explained, associated to the number of heterotactic/syndiotactic triads.