4-二乙氧基硫代膦酰氧基苯胺 | 3735-01-1

• 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: 4-二乙氧基硫代膦酰氧基苯胺
• 英文名称: O-(p-aminophenyl) O,O-diethyl phosphorothioate
• 英文别名: O,O-diethyl O-4-aminophenyl phosphorothioate；O,O-diethyl O-(4-aminophenyl) thiophosphate；aminoparathion；4-diethoxyphosphinothioyloxyaniline
• CAS: 3735-01-1
• 化学式: C₁₀H₁₆NO₃PS
• 分子量: 261.282
• InChiKey: XIZOTXGJXSTQDI-UHFFFAOYSA-N

物化性质

• 熔点：
  147-149 °C
• 沸点：
  346.2±44.0 °C(Predicted)
• 密度：
  1.1577 g/cm3
• 物理描述：
  Solid
• 溶解度：
  0.00 M
• 保留指数：
  1885

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  85.8
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2922199090

反应信息

• 作为反应物：
  描述：

  4-二乙氧基硫代膦酰氧基苯胺 在 间氯过氧苯甲酸 、 维生素 C 作用下， 以 甲醇 为溶剂， 反应 0.33h， 生成 O,O-diethyl O-(4-hydroxyaminophenyl) thiophosphate
  参考文献：
  名称：

  Aminoparathion: A Highly Reactive Metabolite of Parathion. 1. Reactions with Polyphenols and Polyphenol Oxidase

  摘要：

  Spiking of tomato and apple fruits with parathion at different levels of about 1-4 mg/kg irradiation and under simulated sunlight conditions resulted in nearly complete photodegradation within 13 h, but extractable parathion degradation products could not be found in any case. However, after irradiation of an unrealistically spiked apple (134 mg/kg) different photoproducts including aminoparathion (AP) were detectable by HPLC, proving that the hitherto postulated photochemistry of parathion indeed takes place in the fruit cuticle environment. Besides the photoreduction pathway it was shown for the first time that AP is also easily formed by reduction of the primary photoproduct nitrosoparathion with thiols (cysteine, glutathione), while ascorbic acid only leaves hydroxylaminoparathion. In the presence of polyphenols, AP was effectively bound to quinone intermediates formed by both silver oxide and polyphenol oxidases. For pyrocatechol, a disubstituted o-quinone derivative could be isolated as a dark red addition product and structurally be elucidated. However, in the presence of caffeic acid, catechol, naringin, and quercetin, respectively, insoluble dark colored polymers precipitated within 48 h, while in the supernatants AP was not detectable any more. Polymer-bound and nonextractable AP was proven by transesterification with sodium ethoxide releasing O,O,O-triethyl thiophosphate which was determined by GC. Additionally, AP itself was a substrate for polyphenol oxidases, resulting in a quinone imine intermediate which in turn reacted with excessive AP yielding deep red colored di- and trimerization products.

  DOI：

  10.1021/jf051520m
• 作为产物：
  描述：

  巴拉松 在 盐酸 、 sodium carbonate 、 溶剂黄146 、 锌 作用下， 以 乙醚 、 水 为溶剂， 反应 0.75h， 生成 4-二乙氧基硫代膦酰氧基苯胺
  参考文献：
  名称：

  基于小分子半抗原微量滴定板表面之间的共价键的对硫磷敏感免疫测定

  摘要：

  已经开发出用于检测对硫磷的灵敏竞争抑制酶联免疫吸附测定（CIELISA）。在该测定中，将小分子半抗原II（O，O-二乙基O-4-氨基苯基硫代磷酸酯）共价连接至戊二醛处理的微量滴定板。另外，4-（乙氧基（4-硝基苯氧基）磷硫酰氨基）丁酸-卵清蛋白（半抗原I–OVA）偶联物可作为包被抗原，用于与CIELISA格式的直接与半抗原II共价连接的板进行比较。所开发的测定方法显示出高度的敏感性（IC 10为0.08 ng mL -1）的选择性和稳定性。在样品分析中，通过此测定法检测到的对硫磷结果与通过高效液相色谱获得的结果一致。

  DOI：

  10.1007/s13738-016-1009-5

文献信息

• Development of a competitive format sorbent assay for the determination of parathion in water using molecular imprinted polymer as specific sorbent carrier
  作者：Jian She Tang、Li Xiang

  DOI：10.1016/j.cclet.2010.05.014

  日期：2010.11

  A rapid, simple, and reliable competitive molecular imprinted polymer sorbent assay (MIPSA) was developed and validated for measurement of parathion in water samples. This assay employed a molecular imprinted polymer (MIP) that was synthesized with non-covalent imprinting method as capture reagent and p-aminoparathion conjugate of horseradish peroxidase (para-HRP) as an enzyme label. The assay depended on a competitive binding reaction between the enzyme conjugate and analyte for the binding sites of the MIP. The optimized analysis conditions of 10 ng mL(-1) para-HRP and 10 mg mL(-1) polymer were found. The assay was acceptable to detect parathion in water samples under the optimized conditions, with a limit of detection of 50 ng mL(-1). Mean analytical recoveries of added parathion in water samples ranged from 101.2% to 105%. The precision of the assay was satisfactory; relative standard deviation ranged from 4.3% to 6%. (C) 2010 Jian She Tang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• Gupalo, A. P.; Khmilevskaya, M. I.; Turkevich, V. V., Journal of general chemistry of the USSR, 1986, vol. 56, # 6, p. 1108 - 1112
  作者：Gupalo, A. P.、Khmilevskaya, M. I.、Turkevich, V. V.、Vas'kiv, A. P.

  DOI：——

  日期：——
• GUPALO A. P.; XMILEVSKAYA M. I.; TURKEVICH V. V.; VASKIV A. P., ZH. OBSHCH. XIMII, 56,(1986) N 6, 1258-1262
  作者：GUPALO A. P.、 XMILEVSKAYA M. I.、 TURKEVICH V. V.、 VASKIV A. P.

  DOI：——

  日期：——
• A sensitive immunoassay for parathion based on covalent linkage between small molecules hapten microtiter plates surface
  作者：Na Sai、Wenjing Sun、Yuntang Wu、Zhong Sun、Guowei Huang

  DOI：10.1007/s13738-016-1009-5

  日期：2017.1

  A sensitive competitive inhibition enzyme-linked immunosorbent assay (CIELISA) for the detection of parathion has been developed. In this assay, a small molecule hapten II (O,O-diethyl O-4-aminophenyl phosphorothioate) was covalent linked to glutaric dialdehyde treated-microtiter plates. In addition, 4-(ethoxy(4-nitrophenoxy) phosphorothioylamino) butanoic acid-ovalbumin (hapten I–OVA) conjugate served

  已经开发出用于检测对硫磷的灵敏竞争抑制酶联免疫吸附测定（CIELISA）。在该测定中，将小分子半抗原II（O，O-二乙基O-4-氨基苯基硫代磷酸酯）共价连接至戊二醛处理的微量滴定板。另外，4-（乙氧基（4-硝基苯氧基）磷硫酰氨基）丁酸-卵清蛋白（半抗原I–OVA）偶联物可作为包被抗原，用于与CIELISA格式的直接与半抗原II共价连接的板进行比较。所开发的测定方法显示出高度的敏感性（IC 10为0.08 ng mL -1）的选择性和稳定性。在样品分析中，通过此测定法检测到的对硫磷结果与通过高效液相色谱获得的结果一致。
• Aminoparathion: A Highly Reactive Metabolite of Parathion. 1. Reactions with Polyphenols and Polyphenol Oxidase
  作者：Bruno Rung、Wolfgang Schwack

  DOI：10.1021/jf051520m

  日期：2005.11.1

  Spiking of tomato and apple fruits with parathion at different levels of about 1-4 mg/kg irradiation and under simulated sunlight conditions resulted in nearly complete photodegradation within 13 h, but extractable parathion degradation products could not be found in any case. However, after irradiation of an unrealistically spiked apple (134 mg/kg) different photoproducts including aminoparathion (AP) were detectable by HPLC, proving that the hitherto postulated photochemistry of parathion indeed takes place in the fruit cuticle environment. Besides the photoreduction pathway it was shown for the first time that AP is also easily formed by reduction of the primary photoproduct nitrosoparathion with thiols (cysteine, glutathione), while ascorbic acid only leaves hydroxylaminoparathion. In the presence of polyphenols, AP was effectively bound to quinone intermediates formed by both silver oxide and polyphenol oxidases. For pyrocatechol, a disubstituted o-quinone derivative could be isolated as a dark red addition product and structurally be elucidated. However, in the presence of caffeic acid, catechol, naringin, and quercetin, respectively, insoluble dark colored polymers precipitated within 48 h, while in the supernatants AP was not detectable any more. Polymer-bound and nonextractable AP was proven by transesterification with sodium ethoxide releasing O,O,O-triethyl thiophosphate which was determined by GC. Additionally, AP itself was a substrate for polyphenol oxidases, resulting in a quinone imine intermediate which in turn reacted with excessive AP yielding deep red colored di- and trimerization products.

表征谱图