4-nitrophenyl bis(chloromethyl)phosphinate | 33714-89-5

• 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: 4-nitrophenyl bis(chloromethyl)phosphinate
• 英文别名: P,P-bis(chloromethyl)-O-(4-nitrophenyl)phosphinate；4-nitrophenyl-bis(chloromethyl) phosphinate；p-nitrophenyl bis(chloromethyl)phosphinate；4-nitrophenylbis(chloromethyl)phosphinate；p-Nitrophenylbis-(chlormethyl)-phosphinat；Phosphinic acid, bis(chloromethyl)-, p-nitrophenyl ester；1-[bis(chloromethyl)phosphoryloxy]-4-nitrobenzene
• CAS: 33714-89-5
• 化学式: C₈H₈Cl₂NO₄P
• 分子量: 284.036
• InChiKey: YRDHSUNKJUPZEO-UHFFFAOYSA-N

物化性质

• 沸点：
  388.7±52.0 °C(Predicted)
• 密度：
  1.505±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-nitrophenyl bis(chloromethyl)phosphinate 在 2-dimethylaminomethylphenol-copper(II) 、 sodium dodecyl-sulfate 作用下， 以 水 为溶剂， 生成 4-硝基苯酚阴离子
  参考文献：
  名称：

  Effect of sodium dodecyl sulfate on the reactivity of copper(II) complexes with 2-dimethylaminomethylphenol

  摘要：

  The effects of the anionic surfactant sodium dodecyl sulfate on complex formation of 2-dimethylaminomethylphenol (1) with copper(II) in aqueous solutions and on the kinetics of the reactions of copper(II) complexes of 1 with 4-nitrophenylbis(chloromethyl)phosphinate (2) were studied. The reactivities of the complexes in these reactions are higher than that of 1 at all concentrations of SDS studied (0.010-0.200 mol L(-1)) with pH 7-9.

  DOI：

  10.1007/bf01433969
• 作为产物：
  描述：

  bis(chloromethyl)phosphinic chloride 、 4-nitrophenol sodium salt 以 四氢呋喃 为溶剂， 生成 4-nitrophenyl bis(chloromethyl)phosphinate
  参考文献：
  名称：

  有机磷化合物53的制备及其性质-双-（氯甲基）-次膦酸和-硫代次膦酸衍生物以及含有两个ClCH 2基团的叔膦氧化物和硫化物[1]

  摘要：

  通过在等量的酸结合剂存在下用醇，硫醇或胺处理双-氯甲基-次膦酸或-硫代次膦酰氯，以合理的收率形成双-氯甲基-次膦酸酯，-硫代膦酸酯和-次膦酰胺。出乎意料的是，硫代次膦酸酯没有显示出杀虫活性，只有β-枯基衍生物表现出低的除草活性。

  DOI：

  10.1002/hlca.19710540617

文献信息

• Protolytic properties and reactivity of aminomethylated calix[4]resorcarenes in reactions with esters of phosphorus acids
  作者：I. S. Ryzhkina、L. A. Kudryavtseva、A. R. Mustafina、Yu. E. Morozova、E. Kh. Kazakova、K. M. Enikeev、A. I. Konovalov

  DOI：10.1007/bf02496160

  日期：1999.3

  acid-base properties and the kinetics of reactions of aminomethylated calix[4]resorcarenes (AMC) withp-nitrophenyl esters of phosphorus acids in aqueous solutions of propan-2-ol (80 vol.% PriOH) were studied by potentiometry, UV spectrophotometry, and31P NMR spectroscopy. The effect of the length of the hydrocarbon radical and substituents at the nitrogen atom on the protolytic properties and reactivity

  用电位计、紫外分光光度法研究了氨甲基化杯[4]间苯二酚(AMC)与磷酸的对硝基苯酯在丙-2-醇(80 vol.% PriOH)水溶液中的酸碱性质和反应动力学和 31 P NMR 光谱。研究了烃基的长度和氮原子上的取代基对AMC的质子分解性质和反应活性的影响。所研究的反应分两个阶段进行。在第一阶段，形成磷酸化的 AMC，在第二阶段水解成相应的酸。
• Effect of structural preorganization on the reactivity of carbazoylmethyl derivatives of pyrogallol and calix[4]pyrogallol
  作者：T. N. Pashirova、M. V. Leonova、S. N. Podyachev、S. N. Sudakova、L. Ya. Zakharova、L. A. Kudryavtseva、A. I. Konovalov

  DOI：10.1007/s11172-007-0381-9

  日期：2007.12

  The aggregation behavior of carbazoylmethyl derivatives of pyrogallol and calix[4]pyrogallol was studied by conductometry and dynamic light scattering in water-DMF media. The formation of mixed nanoaggregates in the presence of cationic surfactants was revealed. The effect of structural preorganization of these compounds on their reactivity in the acylation by 4-nitrophenylacetate and the catalytic

  通过电导测定法和动态光散射在水-DMF 介质中研究了连苯三酚和杯[4] 连苯三酚的咔唑基甲基衍生物的聚集行为。揭示了在阳离子表面活性剂存在下混合纳米聚集体的形成。研究了这些化合物的结构预组织对其4-硝基苯乙酸酯酰化反应活性和磷酸酯水解催化活性的影响。
• Aggregation and catalytic activity of 2-hydroxybenzylated polyethyleneimines in water-organic solutions
  作者：G. A. Gaynanova、A. V. Yurina、S. S. Lukashenko、E. P. Zhil’tsova、L. Ya. Zakharova、L. A. Kudryavtseva、A. I. Konovalov

  DOI：10.1007/s11172-010-0243-8

  日期：2010.7

  The aggregation of 2-hydroxybenzylated derivatives of polyethyleneimine in a water—DMF medium in the absence and in the presence of cationic surfactants was studied. The catalytic activity of modified polyethyleneimines in hydrolysis of phosphorus acid esters depends on the pH of the medium and increases with the formation of polymer-colloidal complexes. The polymer-colloidal complexes based on surfactants with two hydroxyethyl substituents in the head group have the maximum catalytic activity (increase in the reaction rate by up to three orders of magnitude).

  研究了聚乙烯亚胺的 2-羟基苄基衍生物在没有阳离子表面活性剂和有阳离子表面活性剂的情况下在水-DMF 介质中的聚集情况。改性聚乙烯亚胺在水解磷酸酯时的催化活性取决于介质的 pH 值，并随着聚合物胶体复合物的形成而增加。以头基中含有两个羟乙基取代基的表面活性剂为基础的聚合物-胶体复合物具有最大的催化活性（反应速率最多可提高三个数量级）。
• The reaction of 2-aminomethylphenols and their copper(II) complexes with esters of phosphorus acids
  作者：I. S. Ryzhkina、L. A. Kudryavtseva、K. M. Enikeev、V. I. Morozov、G. A. Boos、Yu. I. Sal'nikov

  DOI：10.1007/bf02495075

  日期：2000.8

  Abstract2-Alkyl- and 2-dialkylaminomethylphenols (AMP) with different hydrophobic substituents at the nitrogen atom and their copper(II) complexes (CAMP) react with the esters of phosphorus acids in aqueous solutions of ethanol in two stages: phosphorylated AMP (PAMP) are formed at the first stage and then hydrolyzed to the corresponding acids. The reactivity of AMP and PAMP significantly decreases

  摘要在氮原子上具有不同疏水取代基的 2-烷基和 2-二烷基氨基甲基苯酚 (AMP) 及其铜 (II) 络合物 (CAMP) 与磷酸酯在乙醇水溶液中分两个阶段反应：磷酸化 AMP (PAMP)在第一阶段形成，然后水解成相应的酸。当氮原子上取代基的疏水性和空间位阻增加时，AMP 和 PAMP 的反应性显着降低。发现了 CAMP 的逆相关性。
• Supramolecular systems based on poly(ethyleneimines) and calix[4]resorcinarenes with alkylphosphonate fragments. Aggregation and catalytic activity
  作者：T. N. Pashirova、S. S. Lukashenko、E. M. Kosacheva、L. Z. Rizvanova、G. A. Gainanova、I. R. Knyazeva、A. R. Burilov、L. A. Kudryavtseva、A. I. Konovalov

  DOI：10.1007/s11172-007-0145-6

  日期：2007.5

  Aggregation in poly(ethylenimine)-calix[4]resorcinarene-water-DMF systems was studied by the methods of conductometry and dynamic light scattering. The sizes (radii) of the aggregates formed and the critical micelle concentrations were determined. The catalytic activity for these systems in the hydrolisys of phosphorus acid esters was shown.

  采用电导法和动态光散射法研究了聚(乙烯亚胺)-杯[4]间苯二酚-水-DMF体系中的聚集现象。确定形成的聚集体的尺寸（半径）和临界胶束浓度。显示了这些系统在磷酸酯水解中的催化活性。