methyl-phosphonic acid 2-methoxy-ethyl ester | 170005-05-7

• 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: methyl-phosphonic acid 2-methoxy-ethyl ester
• 英文别名: 2-methoxyethyl methylphosphonic acid；2-Methoxyethyl methyl-phosphonic acid；2-methoxyethoxy(methyl)phosphinic acid
• CAS: 170005-05-7
• 化学式: C₄H₁₁O₄P
• 分子量: 154.103
• InChiKey: OVJINGLXJWTWBM-UHFFFAOYSA-N

物化性质

• 沸点：
  226.8±42.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  丙醇 、 methyl-phosphonic acid 2-methoxy-ethyl ester 在 silica gel 、 N,N'-二环己基碳二亚胺 作用下， 反应 1.17h， 以76.5%的产率得到O-propyl 2-methoxyethyl methylphosphonate
  参考文献：
  名称：

  Surface-Mediated Synthesis of O-Alkyl 2-Methoxyethyl Alkylphosphonates Under Solvent Free Conditions: Potential Marker of Nerve Agents

  摘要：

  This article describes rapid and efficient surface mediated synthesis of O-alkyl 2-methoxyethyl alkylphosphonates from alkylphosphonic acids and alcohols using dicyclohexyl carbodiimide (DCC)-Celite as a solid support. These compounds are markers of nerve agents. 2-Methoxyethyl methylphosphonic acids (2a-d) were reacted with various alcohols to yield O-alkyl 2-methoxyethyl alkylphosphonates (AMEAPs, 3a-m). This synthetic method has advantages over other methods in terms of selectivity, shorter reaction time, high yield, and easy work-up.

  DOI：

  10.1080/10426500903496705
• 作为产物：
  描述：

  乙二醇甲醚 、 甲基膦酸 在 苯胂酸 作用下， 以 甲苯 为溶剂， 生成 methyl-phosphonic acid 2-methoxy-ethyl ester
  参考文献：
  名称：

  PREPARATION, DERIVATIZATION WITH TRIMETHYLSILYLDIAZOMETHANE, AND GC/MS ANALYSIS OF A “POOL” OF ALKYL METHYLPHOSPHONIC ACIDS FOR USE AS QUALITATIVE STANDARDS IN SUPPORT OF COUNTERTERRORISM AND THE CHEMICAL WEAPONS CONVENTION

  摘要：

  There are hundreds of nerve agents in the class of alkyl methylphosphonofluoridates covered by Schedule 1 of the CWC (Chemical Weapons Convention). Hydrolysis of these sarin-like nerve agents results in all equal number of alkyl methylphosphonic acids. These allkyl methylphosphonic acids are persistent and provide good evidence of specific agent production or use. In order to support the CWC and counterterrorism activities, it is desirable to have ready access to each of these hydrolysis products for use as qualitative standards. A means for simultaneously producing multiple alkyl methylphosphonates from methylphosphonic acid and the corresponding alcohols was developed. Derivatization of these alkyl methylphosphonic acids with trimethylsilyldiazomethane yields the corresponding methyl esters which are suitable for GC/MS analysis.

  DOI：

  10.1080/10426500490459632

文献信息

• PREPARATION, DERIVATIZATION WITH TRIMETHYLSILYLDIAZOMETHANE, AND GC/MS ANALYSIS OF A “POOL” OF ALKYL METHYLPHOSPHONIC ACIDS FOR USE AS QUALITATIVE STANDARDS IN SUPPORT OF COUNTERTERRORISM AND THE CHEMICAL WEAPONS CONVENTION
  作者：Michael D. Crenshaw、David B. Cummings

  DOI：10.1080/10426500490459632

  日期：2004.6

  There are hundreds of nerve agents in the class of alkyl methylphosphonofluoridates covered by Schedule 1 of the CWC (Chemical Weapons Convention). Hydrolysis of these sarin-like nerve agents results in all equal number of alkyl methylphosphonic acids. These allkyl methylphosphonic acids are persistent and provide good evidence of specific agent production or use. In order to support the CWC and counterterrorism activities, it is desirable to have ready access to each of these hydrolysis products for use as qualitative standards. A means for simultaneously producing multiple alkyl methylphosphonates from methylphosphonic acid and the corresponding alcohols was developed. Derivatization of these alkyl methylphosphonic acids with trimethylsilyldiazomethane yields the corresponding methyl esters which are suitable for GC/MS analysis.
• Surface-Mediated Synthesis of <i>O-A</i>lkyl 2-Methoxyethyl Alkylphosphonates Under Solvent Free Conditions: Potential Marker of Nerve Agents
  作者：Rajesh Kumar、A. K. Gupta、M. P. Kaushik

  DOI：10.1080/10426500903496705

  日期：2010.9.27

  This article describes rapid and efficient surface mediated synthesis of O-alkyl 2-methoxyethyl alkylphosphonates from alkylphosphonic acids and alcohols using dicyclohexyl carbodiimide (DCC)-Celite as a solid support. These compounds are markers of nerve agents. 2-Methoxyethyl methylphosphonic acids (2a-d) were reacted with various alcohols to yield O-alkyl 2-methoxyethyl alkylphosphonates (AMEAPs, 3a-m). This synthetic method has advantages over other methods in terms of selectivity, shorter reaction time, high yield, and easy work-up.