dimethyl (2-chloro-5-methylphenyl)phosphonate | 920266-98-4

• 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: dimethyl (2-chloro-5-methylphenyl)phosphonate
• 英文别名: Dimethyl (2-chloro-5-methylphenyl)phosphonate；1-chloro-2-dimethoxyphosphoryl-4-methylbenzene
• CAS: 920266-98-4
• 化学式: C₉H₁₂ClO₃P
• 分子量: 234.619
• InChiKey: RJUSSXXADYYGSM-UHFFFAOYSA-N

物化性质

• 沸点：
  85-92 °C(Press: 1 Torr)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-chloroacetylenephosphonic acid dimethyl ester 、 天然橡胶 在 对苯二酚 、 aluminum oxide 、 potassium permanganate 作用下， 以 丙酮 为溶剂， 反应 12.0h， 生成 dimethyl (2-chloro-4-methylphenyl)phosphonate 、 dimethyl (2-chloro-5-methylphenyl)phosphonate
  参考文献：
  名称：

  A methodology for synthesis of primary o-phenylenebisphosphines and o-chlorophenylphosphines

  摘要：

  On the basis of the reaction of ethynediylbisphosphonates and chloroethynylphosphonates with classical donor alka-1,3-dienes, a general strategy for synthesis of o-bisphosphanylbenzenes and o-chlorophosphanylbenzenes, which includes two consecutive steps: Diels-Alder condensation -> aromatization of the carbocyclic phosphonate (bisphosphonate) formed -> reduction of the phosphonate groups, was developed. Convenient procedures are devised for aromatization of phosphorus-containing cyclohexa-1,4-dienes and for reduction of o-phenylenebisphosphonates and o-clorophenylphosphonates to primary phosphines. A series of new alkylsubstituted phosphonic chlorides were prepared, and a possibility of functionalization of methyl-substituted o-phenylenebisphosphonates and o-clorophenylphosphonates by the methyl groups is demonstrated.

  DOI：

  10.1134/s1070363206060089

文献信息

• A methodology for synthesis of primary o-phenylenebisphosphines and o-chlorophenylphosphines
  作者：S. N. Tverdomed、A. V. Dogadina、B. I. Ionin

  DOI：10.1134/s1070363206060089

  日期：2006.6

  On the basis of the reaction of ethynediylbisphosphonates and chloroethynylphosphonates with classical donor alka-1,3-dienes, a general strategy for synthesis of o-bisphosphanylbenzenes and o-chlorophosphanylbenzenes, which includes two consecutive steps: Diels-Alder condensation -> aromatization of the carbocyclic phosphonate (bisphosphonate) formed -> reduction of the phosphonate groups, was developed. Convenient procedures are devised for aromatization of phosphorus-containing cyclohexa-1,4-dienes and for reduction of o-phenylenebisphosphonates and o-clorophenylphosphonates to primary phosphines. A series of new alkylsubstituted phosphonic chlorides were prepared, and a possibility of functionalization of methyl-substituted o-phenylenebisphosphonates and o-clorophenylphosphonates by the methyl groups is demonstrated.