1,4-bis(vinylthio)butane | 36648-04-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1,4-bis(vinylthio)butane
• 英文别名: 1,4-bis(vinylthio)-n-butane；1.4-Bis-vinylmercapto-butan；1.4-Divinylmercapto-butan；1,4-Di-(thiovinyl)-butan；1,1'-butane-1,4-diylbissulfanyl-bis-ethene；1,4-bis-vinylsulfanyl-butane；1,4-Bis(ethenylsulfanyl)butane
• CAS: 36648-04-1
• 化学式: C₈H₁₄S₂
• 分子量: 174.331
• InChiKey: DHJVCSJNAGATMB-UHFFFAOYSA-N

物化性质

• 沸点：
  83 °C(Press: 0.7 Torr)
• 密度：
  0.975±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  10
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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(vinylthio)butane 在 氢氧化钾 作用下， 以 甲醇 、 六甲基磷酰三胺 、 二甲基亚砜 为溶剂， 生成 1,4-bis-(2-vinylsulfanyl-ethylsulfanyl)-butane
  参考文献：
  名称：

  Method for synthesis of?,?-unsaturated sulfides from dithiolacetates

  摘要：

  DOI：

  10.1007/bf00854503
• 作为产物：
  描述：

  calcium carbide 、 1,4-丁二硫醇 在 水 、 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以89%的产率得到1,4-bis(vinylthio)butane
  参考文献：
  名称：

  Calcium carbide as a convenient acetylene source in the synthesis of unsaturated sulfides, promising functionalized monomers

  摘要：

  Calcium carbide was studied as a useful solid-state reagent to incorporate acetylene unit into synthetic procedures. Atom-economic thiol-yne click reaction was successfully performed with single and double additions. Heterocyclic thiols and aliphatic dithiols reacted with acetylene generated in situ from calcium carbide to afford corresponding vinyl sulfides and bis(thiovinyl)ethers in good to high yields.

  DOI：

  10.1016/j.mencom.2015.11.004

文献信息

• Mass Spectral Studies on Vinylic Degradation Products of Sulfur Mustards under Gas Chromatography/Mass Spectrometry Conditions
  作者：L. Sai Sachin、R. Karthikraj、K. Kalyan Kumar、T. Sony、N. Prasada Raju、S. Prabhakar

  DOI：10.1255/ejms.1398

  日期：2015.12

  Sulfur mustards are a class of vesicant chemical warfare agents that rapidly degrade in environmental samples. The most feasible degradation products of sulfur mustards are chloroethyl vinylic compounds and divinylic compounds, which are formed by the elimination of one and two HCl molecules from sulfur mustards, respectively. The detection and characterization of these degradation products in environmental samples are an important proof for the verification of sulfur mustard usage. In this study, we synthesized a set of sulfur mustard degradation products, i.e., divinylic compounds (1–7) and chloroethyl vinylic compounds (8–14), and characterized using gas chromatography/mass spectrometry (GC/MS) under electron ionization (EI) and chemical ionization (CI) (methane) conditions. The EI mass spectra of the studied compounds mainly included the fragment ions that resulted from homolytic cleavages with or without hydrogen migrations. The divinylic compounds (1–7) showed [M – SH]⁺ ions, whereas the chloroethylvinyl compounds (8–14) showed [M – Cl]⁺ and [M – CH₂CH₂Cl]⁺ ions. Methane/CI mass spectra showed [M + H]⁺ ions and provided molecular weight information. The GC retention index (RI) values were also calculated for the studied compounds. The EI and CI mass spectral data together with RI values are extremely useful for off-site analysis for the verification of the chemical weapons convention and also to participate in official Organization for the Prohibition of Chemical Weapons proficiency tests.

  硫芥子是一类气泡剂化学战剂，它们在环境样品中迅速降解。硫芥子最可行的降解产物是氯乙基乙烯化合物和二乙烯化合物，它们分别通过从硫芥子中消除一个和两个HCl分子形成。在环境样品中检测和表征这些降解产物对于验证硫芥子的使用是重要的证据。在这项研究中，我们合成了一组硫芥子降解产物，即二乙烯化合物（1-7）和氯乙基乙烯化合物（8-14），并使用气相色谱/质谱联用（GC/MS）在电子电离（EI）和化学电离（CI）（甲烷）条件下进行表征。研究化合物的EI质谱主要包括由于有或无氢迁移而导致的自由裂解的碎片离子。二乙烯化合物（1-7）显示[M - SH]⁺离子，而氯乙基乙烯化合物（8-14）显示[M - Cl]⁺和[M - CH₂CH₂Cl]⁺离子。甲烷/CI质谱显示[M + H]⁺离子并提供分子量信息。还计算了研究化合物的GC保留指数（RI）值。EI和CI质谱数据以及RI值对于离线分析以验证化学武器公约以及参加官方禁化武组织的熟练测试非常有用。