(2-dodecasulfanyl-ethyl)-phosphonic acid | 920279-24-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: (2-dodecasulfanyl-ethyl)-phosphonic acid
• 英文别名: [2-(Dodecylsulfanyl)ethyl]phosphonic acid；2-dodecylsulfanylethylphosphonic acid
• CAS: 920279-24-9
• 化学式: C₁₄H₃₁O₃PS
• 分子量: 310.438
• InChiKey: MBAKOZIAEBSQTA-UHFFFAOYSA-N

物化性质

• 熔点：
  89 °C(Solv: acetone (67-64-1))
• 沸点：
  458.4±47.0 °C(Predicted)
• 密度：
  1.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  82.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙烯基膦酸 、 十二硫醇 在 偶氮二异丁腈 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以80%的产率得到(2-dodecasulfanyl-ethyl)-phosphonic acid
  参考文献：
  名称：

  New alkylated and perfluoroalkylated phosphonic acids: Synthesis, adhesive and water-repellent properties on aluminum substrates

  摘要：

  This paper describes the synthesis of phosphonic acids (R-S-(CH2)(2)-PO(OH)(2)) containing a perfluoroalkylated chain (R = C6F13-(CH2)(2), C8F17-(CH2)(2)) or an alkyl group (R = C12H25, C18H37). These compounds, obtained in excellent yield by telomerization of vinyl phosphonic acid in the presence of alkylated or perfluorinated mercaptans used as transfer agents, were characterized by H-1, F-19 and P-31 nuclear magnetic resonance. Thermal characterization by differential scanning calorimetry (DSC) showed the presence of mesophases for compounds containing C8F17 and C18H37 end groups. A lamellar structure with a layered or bilayered organization was identified by small angle X-ray scattering (SAXS). Adhesion of these compounds on aluminum surfaces is improved by the presence of phosphonic groups. Hydrophobic properties of coated aluminum surfaces are enhanced by fluorinated groups. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2006.03.003

文献信息

• New alkylated and perfluoroalkylated phosphonic acids: Synthesis, adhesive and water-repellent properties on aluminum substrates
  作者：M. Essahli、M. El Asri、A. Boulahna、M. Zenkouar、M. Viguier、Y. Hervaud、B. Boutevin

  DOI：10.1016/j.jfluchem.2006.03.003

  日期：2006.7

  This paper describes the synthesis of phosphonic acids (R-S-(CH2)(2)-PO(OH)(2)) containing a perfluoroalkylated chain (R = C6F13-(CH2)(2), C8F17-(CH2)(2)) or an alkyl group (R = C12H25, C18H37). These compounds, obtained in excellent yield by telomerization of vinyl phosphonic acid in the presence of alkylated or perfluorinated mercaptans used as transfer agents, were characterized by H-1, F-19 and P-31 nuclear magnetic resonance. Thermal characterization by differential scanning calorimetry (DSC) showed the presence of mesophases for compounds containing C8F17 and C18H37 end groups. A lamellar structure with a layered or bilayered organization was identified by small angle X-ray scattering (SAXS). Adhesion of these compounds on aluminum surfaces is improved by the presence of phosphonic groups. Hydrophobic properties of coated aluminum surfaces are enhanced by fluorinated groups. (c) 2006 Elsevier B.V. All rights reserved.