1,4-bis[(butylsulfanyl)methyl]benzene | 177752-90-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,4-bis[(butylsulfanyl)methyl]benzene
• 英文别名: α,α'-bis(n-butylthio)-p-xylene；1,4-Bis(butylsulfanylmethyl)benzene
• CAS: 177752-90-8
• 化学式: C₁₆H₂₆S₂
• 分子量: 282.514
• InChiKey: VAMJSEHMOOUGSJ-UHFFFAOYSA-N

物化性质

• 沸点：
  385.0±22.0 °C(Predicted)
• 密度：
  1.001±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-bis[(butylsulfanyl)methyl]benzene 在 盐酸 、 tellurium oxide 、 双氧水 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以60%的产率得到1,4-bis[(butylsulfinyl)methyl]benzene
  参考文献：
  名称：

  Identification and Quantification of Polymerization Defects in ¹³C-Labeled Sulfinyl and Gilch OC₁C₁₀−PPV by NMR Spectroscopy

  摘要：

  By using selectively C-13-labeled sulfinyl and Gilch polymers, only noneliminated groups were demonstrated to be present in significant amounts (ca. 6.9%) in the sulfinyl conjugated OC1C10-PPV. By means of a two-step elimination procedure, this amount could be reduced to a level less than 0.5%. In the Gilch route on the other hand, a tolane-bisbenzyl unit was confirmed to be the main structural defect. Furthermore, noneliminated groups were clearly present. For both polymerization routes no indications for other types of defects such as cross-links or branching, were detected while strong indications for carbonyl type end groups were found. The nature of all "defects" was elucidated by applying liquid 1D and 2D NMR spectroscopy and the amount was calculated based on fully quantitative C-13 NMR spectra.

  DOI：

  10.1021/ma030025t
• 作为产物：
  描述：

  丁硫醇 、 1,4-对二氯苄 在 sodium t-butanolate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 以98%的产率得到1,4-bis[(butylsulfanyl)methyl]benzene
  参考文献：
  名称：

  Identification and Quantification of Polymerization Defects in ¹³C-Labeled Sulfinyl and Gilch OC₁C₁₀−PPV by NMR Spectroscopy

  摘要：

  By using selectively C-13-labeled sulfinyl and Gilch polymers, only noneliminated groups were demonstrated to be present in significant amounts (ca. 6.9%) in the sulfinyl conjugated OC1C10-PPV. By means of a two-step elimination procedure, this amount could be reduced to a level less than 0.5%. In the Gilch route on the other hand, a tolane-bisbenzyl unit was confirmed to be the main structural defect. Furthermore, noneliminated groups were clearly present. For both polymerization routes no indications for other types of defects such as cross-links or branching, were detected while strong indications for carbonyl type end groups were found. The nature of all "defects" was elucidated by applying liquid 1D and 2D NMR spectroscopy and the amount was calculated based on fully quantitative C-13 NMR spectra.

  DOI：

  10.1021/ma030025t

文献信息

• Highly Selective Route for Producing Unsymmetrically Substituted Monomers toward Synthesis of Conjugated Polymers Derived from Poly(<i>p</i>-phenylene vinylene)
  作者：Albert J. J. M. van Breemen、Dirk J. M. Vanderzande、Peter J. Adriaensens、Jan M. J. V. Gelan

  DOI：10.1021/jo9821022

  日期：1999.4.1

  A new convenient route for producing unsymmetrically substituted sulfinyl monomers of precursor polymers toward poly(p-phenylene vinylene) is described. Upon treating a symmetrical bissulfonium salt with a thiolate anion, an unexpected high selectivity for the monosubstituted thioethers (90%) is obtained. Optimization of the reaction conditions showed that the stoichiometry of the reactants in this

  描述了一种制备前体聚合物的不对称取代的亚磺酰基单体向聚对苯撑亚乙烯基的简便方法。用硫醇盐阴离子处理对称的双s盐时，获得了对单取代硫醚的出乎意料的高选择性（90％）。反应条件的优化表明，该反应中反应物的化学计量对于确保高选择性和防止不希望的副反应很重要。等摩尔量的试剂在环境温度下反应可获得最佳结果。提出了与这些结果一致的机理，并得到了紫外线可见光实验的支持。硫醚的选择性氧化产生亚磺酰基单体。通过使用此新路线，可以将总产量提高2倍
• Scope and Limitations of a New Highly Selective Synthesis of Unsymmetrical Monomers for the Synthesis of Precursors toward Poly(arylenevinylene)s
  作者：Michael Van Der Borght、Dirk Vanderzande、Peter Adriaensens、Jan Gelan

  DOI：10.1021/jo990111k

  日期：2000.1.1

  In our laboratory a precursor route to poly(p-phenylenevinylene) derivatives is developed in which unsymmetrically substituted p-xylene derivatives, possessing a benzylic sulfinylalkyl group, are used as monomers. Because of this unsymmetry, we were forced to investigate thoroughly the synthesis of these sulfoxides, as we start from symmetric and readily accessible molecules, namely, bis(halomethyl)-p-xylene

  在我们的实验室中，开发了一种制备聚对对苯乙炔衍生物的前体路线，其中使用具有亚苄基亚磺酰基烷基的不对称取代的对二甲苯衍生物作为单体。由于这种不对称性，我们被迫彻底研究这些亚砜的合成，因为我们从对称且易于获得的分子即双（卤代甲基）-对二甲苯衍生物开始。在以前的出版物中，提出了生产这些不对称取代的亚磺酰基单体的极其有效的新途径。本文扩展了这些先前报告的结果。为了检查这种优雅路线的范围和局限性，将该新方法应用于初始工作中未包括的各种衍生物的合成。
• A process for producing polymers of alpha,omega-unsaturated conjugated compounds
  申请人：Aventis Research & Technologies GmbH & Co. KG

  公开号：EP0705857B1

  公开（公告）日：2000-01-19
• US5763539A
  申请人：——

  公开号：US5763539A

  公开（公告）日：1998-06-09
• Identification and Quantification of Polymerization Defects in ¹³C-Labeled Sulfinyl and Gilch OC₁C₁₀−PPV by NMR Spectroscopy
  作者：H. Roex、P. Adriaensens、D. Vanderzande、J. Gelan

  DOI：10.1021/ma030025t

  日期：2003.7.1

  By using selectively C-13-labeled sulfinyl and Gilch polymers, only noneliminated groups were demonstrated to be present in significant amounts (ca. 6.9%) in the sulfinyl conjugated OC1C10-PPV. By means of a two-step elimination procedure, this amount could be reduced to a level less than 0.5%. In the Gilch route on the other hand, a tolane-bisbenzyl unit was confirmed to be the main structural defect. Furthermore, noneliminated groups were clearly present. For both polymerization routes no indications for other types of defects such as cross-links or branching, were detected while strong indications for carbonyl type end groups were found. The nature of all "defects" was elucidated by applying liquid 1D and 2D NMR spectroscopy and the amount was calculated based on fully quantitative C-13 NMR spectra.