O,O-二甲基-N-乙酰基硫代磷酰胺 | 42072-27-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫代磷酸及其衍生物
• 中文名称: O,O-二甲基-N-乙酰基硫代磷酰胺
• 英文名称: O,O-dimethyl N-acetylphosphoramidothioate
• 英文别名: O,O-dimethyl-N-acetylphosphoroamidothioate；O,O-Dimethyl acetylthiophosphoramidate；N-dimethoxyphosphinothioylacetamide
• CAS: 42072-27-5
• 化学式: C₄H₁₀NO₃PS
• 分子量: 183.168
• InChiKey: QXKNLUMRVZYMRN-UHFFFAOYSA-N

物化性质

• 密度：
  1.261±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  79.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2931900090

制备方法与用途

化学性质 工业品酰化物是一种淡黄色或无色液体，相对密度1.27，在静置时会固化。纯品熔点为50.5℃，分解温度为154.5℃。常温下稳定，能溶于丙酮、二氯乙烷、氯仿等有机溶剂，并且稍溶于水。

用途 O, O-二甲基-N-乙酰基硫代磷酰胺（简称酰化物）是有机磷杀虫剂乙酰甲胺磷的中间体。

生产方法 其制备方法是以精胺为原料进行乙酰化反应。将一定量的精胺和冰醋酸加入到乙酰化反应釜中，搅拌并冷却至0℃以下，在微负压条件下滴加三氯化磷，并控制温度在43℃左右。滴完后继续保温反应10分钟，在真空下抽除氯化氢气体30分钟后冷却至15℃，然后滴加氨水进行中和，确保温度不超过30℃，使pH值达到6～7。静置分层后，所得到的油层即为所需的酰化物。

反应信息

• 作为反应物：
  描述：

  O,O-二甲基-N-乙酰基硫代磷酰胺 在 ammonium sulfide 、 硫化氢 作用下， 以98%的产率得到S-ammonium-N-acetoyl-O-methylphosphoroamidothioate
  参考文献：
  名称：

  S-Ammonium-O-hydrocarbyl-N-acyl phosphoramidothioate salt production and

  摘要：

  将O,O-二烷基-N-酰基磷氨基硫酸盐与氨基硫化物或多硫化物在液氨反应介质中反应制备S-铵盐。

  公开号：

  US03957928A1
• 作为产物：
  描述：

  精胺 、 乙酸酐 在 磷酸 作用下， 反应 1.0h， 生成 O,O-二甲基-N-乙酰基硫代磷酰胺
  参考文献：
  名称：

  Development of an Enzyme-Linked Immunosorbent Assay for the Detection of the Organophosphorus Insecticide Acephate

  摘要：

  A competitive indirect enzyme-linked immunosorbent assay (ciELISA) for the organophosphorus insecticide acephate, 0,S-dimethyl acetylphosphoramidothioate, was developed using a polyclonal antibody. Five different haptens mimicking the analyte were synthesized and conjugated with the carrier proteins bovine serum albumin (BSA) and keyhole limpet hemocyanin (KLH) by the N-hydroxysuccinimide active ester and diazotization methods. Polyclonal antibodies raised against hapten-KLH conjugates in rabbits and hapten-BSA conjugates as coating antigens were screened and selected for the assay in the homologous and heterologous ELISA systems. The effects of various assay conditions such as detergent, organic solvents, pH, and preincubation of the mixture of the polyclonal antibody and the analyte on the sensitivity were evaluated. The IC50 value for acephate was 25 ng/mL in an optimized heterologous system using hapten-4-BSA as a coating antigen and a polyclonal antibody no. 8377 against hapten-1-KLH, showing the detection range of 5-140 ng/ mL and the lowest detection limit of 2 ng/mL. The cross-reactivities of the structurally related organophosphorus insecticides, including the major metabolite of the analyte, methamidophos, were less than 1%. Recoveries from the analyte-fortified tap water, mulberry leaves, and lettuce samples in the assay were in the range of 72-121% by simple extraction, concentration, and dilution. These results indicate that the ELISA could be a convenient and supplemental analytical tool for monitoring acephate residues in environmental and agricultural samples.

  DOI：

  10.1021/jf021020i

文献信息

• Synthesis and Characterization of O,S-Dimethylphosphoramidothioate and N-Acetyl O,S-Dimethylphosphoramidothioate
  作者：S. Ghadimi、S. L. Mousavi、Z. Rahnama、M. Rahimi

  DOI：10.1080/10426500902797079

  日期：2010.1.29

  O,S-Dimethylphosphoramidothioate (methamidophos) and N-acetyl O,S-dimethylphos- phoramidothioate (acephate) were synthesized by new methods to investigate the structure-activity study of acetyl cholinesterase (AChE) inhibition through the parameters of logP, 31P, and IC50. After their characterization by NMR (31P, 31P1H}, 13C, and 1H), IR, and mass spectroscopy, logP and 31P (31P chemical shift in NMR) were used to evaluate lipophilicity and electronical properties. The logP values for methamidophos and acephate were experimentally determined by the GC-shake-flask method, and the ability of the compounds to inhibit human AChE was evaluated by a modified Ellman's assay. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.