(2-chloroethyl) (naphthalen-2-yl) sulfide | 35374-43-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2-chloroethyl) (naphthalen-2-yl) sulfide
• 英文别名: β-Chlorethyl-2-napthyl-thioether；NpSim；(2-chloro-ethyl)-[2]naphthyl sulfide；(2-Chlor-aethyl)-[2]naphthyl-sulfid；2-Chlor-1-(naphthyl-(2)-mercapto)-aethan；2-(Naphthyl-(2)-mercapto)-aethylchlorid；2-(2-Chlor-aethylmercapto)-naphthalin；Naphthalene, 2-[(2-chloroethyl)thio]-；2-(2-chloroethylsulfanyl)naphthalene
• CAS: 35374-43-7
• 化学式: C₁₂H₁₁ClS
• mdl: MFCD12188772
• 分子量: 222.738
• InChiKey: AJHWGOSSSHMWPC-UHFFFAOYSA-N

物化性质

• 熔点：
  53 °C
• 沸点：
  354.7±25.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  (2-chloroethyl) (naphthalen-2-yl) sulfide 在 sodium perborate 、 溶剂黄146 作用下， 反应 3.0h， 以75%的产率得到2-(2-氯乙基磺酰基)萘
  参考文献：
  名称：

  Locus-Specific Microemulsion Catalysts for Sulfur Mustard (HD) Chemical Warfare Agent Decontamination

  摘要：

  The rates of catalytic oxidative decontamination of the chemical warfare agent (CWA) sulfur mustard (HD, bis(2-chlororethyl) sulfide) and a range (chloroethyl) sulfide simulants of variable lipophilicity have been examined using a hydrogen peroxide-based microemulsion system. SANS (small-angle neutron scattering), SAXS (small-angle X-ray scattering), PGSE-NMR (pulsed-gradient spin-echo NMR), fluorescence quenching, and electrospray mass spectroscopy (ESI-MS) were implemented to examine the distribution of HD, its simulants, and their oxidation/hydrolysis products in a model oil-in-water microemulsion. These measurements not only present a means of interpreting decontamination rates but also a rationale for the design of oxidation catalysts for these toxic materials. Here we show that by localizing manganese-Schiff base catalysts at the oil droplet-water interface or within the droplet core, a range of (chloroethyl) sulfides, including HD, spanning some 7 orders of octanol-water partition coefficient (K-ow), may be oxidized with equal efficacy using dilute (5 wt. % of aqueous phase) hydrogen peroxide as a noncorrosive, environmentally benign oxidant (e.g., t(1/2) (HD) similar to 18 s, (2-chloroethyl phenyl sulfide, C6H5SCH2CH2Cl) similar to 15 s, (thiodiglycol, S(CH2CH2OH)(2)) similar to 19 s {20 degrees C}). Our observations demonstrate that by programming catalyst lipophilicity to colocalize catalyst and substrate, the inherent compartmentalization of the microemulsion can be exploited to achieve enhanced rates of reaction or to exert control over product selectivity. A combination of SANS, ESI-MS and fluorescence quenching measurements indicate that the enhanced catalytic activity is due to the locus of the catalyst and not a result of partial hydrolysis of the substrate.

  DOI：

  10.1021/ja901872y
• 作为产物：
  描述：

  2-萘硫醇 在 氢氧化钾 、 五氯化磷 作用下， 生成 (2-chloroethyl) (naphthalen-2-yl) sulfide
  参考文献：
  名称：

  15.一硫代乙二醇。第四部分。芳基β-羟基-和β-氯-乙基硫化物

  摘要：

  DOI：

  10.1039/jr9330000046

文献信息

• Divergent electrolysis for the controllable coupling of thiols with 1,2-dichloroethane: a mild approach to sulfide and sulfoxide
  作者：Fei Ling、Tao Liu、Chao Xu、Jiaying He、Wangqin Zhang、Changwu Ling、Lei Liu、Weihui Zhong

  DOI：10.1039/d1gc03440e

  日期：——

  Organosulfurs are important commodity chemicals and indispensable synthetic intermediates in modern chemistry that were traditionally synthesized using metal catalysts, oxidants or strong bases, which caused numerous environmental pollution issues. The divergent synthesis of these scaffolds via a single catalysis under catalyst and oxidant free conditions is a fantastic idea to overcome these drawbacks

  有机硫是现代化学中重要的大宗化学品和不可缺少的合成中间体，传统上采用金属催化剂、氧化剂或强碱合成，造成了诸多环境污染问题。这些支架的不同合成通过在无催化剂和无氧化剂条件下的单一催化是克服这些缺点的绝妙想法。在这里，我们报告了一种安全、实用和环保的电化学方法，用于 1,2-二氯乙烷 (DCE) 与硫醇的可控脱氯偶联，提供增值的 β-氯乙基硫，作为高效后期的通用构件。 -阶段转化为生物活性分子。该协议的温和性和实用性进一步证明了抗痛风药物磺吡酮的全合成，三步总收率为 32%。
• Abdel-Wahab, Aboel-Magd A.; El-Khawaga, Ahmed M.; El-Zohry, Maher F., Phosphorus and Sulfur and the Related Elements, 1984, vol. 19, p. 31 - 44
  作者：Abdel-Wahab, Aboel-Magd A.、El-Khawaga, Ahmed M.、El-Zohry, Maher F.、Khalaf, Ali A.

  DOI：——

  日期：——
• Locus-Specific Microemulsion Catalysts for Sulfur Mustard (HD) Chemical Warfare Agent Decontamination
  作者：Ian A. Fallis、Peter C. Griffiths、Terence Cosgrove、Cecile A. Dreiss、Norman Govan、Richard K. Heenan、Ian Holden、Robert L. Jenkins、Stephen J. Mitchell、Stuart Notman、Jamie A. Platts、James Riches、Thomas Tatchell

  DOI：10.1021/ja901872y

  日期：2009.7.22

  The rates of catalytic oxidative decontamination of the chemical warfare agent (CWA) sulfur mustard (HD, bis(2-chlororethyl) sulfide) and a range (chloroethyl) sulfide simulants of variable lipophilicity have been examined using a hydrogen peroxide-based microemulsion system. SANS (small-angle neutron scattering), SAXS (small-angle X-ray scattering), PGSE-NMR (pulsed-gradient spin-echo NMR), fluorescence quenching, and electrospray mass spectroscopy (ESI-MS) were implemented to examine the distribution of HD, its simulants, and their oxidation/hydrolysis products in a model oil-in-water microemulsion. These measurements not only present a means of interpreting decontamination rates but also a rationale for the design of oxidation catalysts for these toxic materials. Here we show that by localizing manganese-Schiff base catalysts at the oil droplet-water interface or within the droplet core, a range of (chloroethyl) sulfides, including HD, spanning some 7 orders of octanol-water partition coefficient (K-ow), may be oxidized with equal efficacy using dilute (5 wt. % of aqueous phase) hydrogen peroxide as a noncorrosive, environmentally benign oxidant (e.g., t(1/2) (HD) similar to 18 s, (2-chloroethyl phenyl sulfide, C6H5SCH2CH2Cl) similar to 15 s, (thiodiglycol, S(CH2CH2OH)(2)) similar to 19 s 20 degrees C}). Our observations demonstrate that by programming catalyst lipophilicity to colocalize catalyst and substrate, the inherent compartmentalization of the microemulsion can be exploited to achieve enhanced rates of reaction or to exert control over product selectivity. A combination of SANS, ESI-MS and fluorescence quenching measurements indicate that the enhanced catalytic activity is due to the locus of the catalyst and not a result of partial hydrolysis of the substrate.
• 15. Monothioethylene glycol. Part IV. Aryl β-hydroxy- and β-chloro-ethyl sulphides
  作者：George Baddeley、G. Macdonald Bennett

  DOI：10.1039/jr9330000046

  日期：——