O,O-dimethyl O-(3-formyl-4-nitro)phenyl phosphorothioate | 59417-72-0

• 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
• 英文名称: O,O-dimethyl O-(3-formyl-4-nitro)phenyl phosphorothioate
• 英文别名: O,O-dimethyl O-(4-nitro-m-formylphenyl)phosphorothioate；formylfenitrothion；Phosphorothioic acid, O,O-dimethyl O-(3-formyl-4-nitrophenyl) ester；5-dimethoxyphosphinothioyloxy-2-nitrobenzaldehyde
• CAS: 59417-72-0
• 化学式: C₉H₁₀NO₆PS
• 分子量: 291.221
• InChiKey: FTYFFKWTWYUKLS-UHFFFAOYSA-N

物化性质

• 沸点：
  398.3±52.0 °C(Predicted)
• 密度：
  1.469±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  O,O-dimethyl O-(3-formyl-4-nitro)phenyl phosphorothioate 在 二甲基二环氧乙烷 作用下， 以100%的产率得到O,O-dimethyl O-(3-formyl-4-nitro)phenyl phosphate
  参考文献：
  名称：

  Unequivocal Identification of Compounds Formed in the Photodegradation of Fenitrothion in Water/Methanol and Proposal of Selected Transformation Pathways

  摘要：

  The photodegradation of fenitrothion was examined in a mixture of distilled water/methanol (5:1), The UV irradiation was carried out with a high-pressure Hg lamp during 7 h. For the identification of further breakdown products, fenitrooxon and carboxyfenitrothion were also irradiated under experimental conditions identical to those for fenitrothion. The identification of the breakdown products formed was carried out by gas chromatography-mass spectrometry (GC-MS) with electron impact (EI) and comparison with authentic standards synthesized in the laboratory. A total of 21 photoproducts of oxidation, isomerization, denitration, and solvolysis that may be of concern in environmental studies were unequivocally identified. Among them were formyldenitrofenitrothion, carbomethoxydenitro-fenitrooxon, and hydroxymethyldenitrofenitrooxon. A proposed mechanism of the process is presented. Selected pathways for the photodegradation of fenitrothion were examined: (i) degradation through hydrolysis, with eventual remethylation; (ii) P=S to P=O oxidation; (iii) denitration; and (iv) oxidation of the methyl substituent through hydroxymethyl and formyl to give the corresponding carboxy derivatives.

  DOI：

  10.1021/jf00039a044
• 作为产物：
  描述：

  5-羟基-2-硝基苯甲醛 、 二甲基硫代磷酰氯 在 sodium hydroxide 作用下， 以 丙酮 、 苯 为溶剂， 反应 8.0h， 生成 O,O-dimethyl O-(3-formyl-4-nitro)phenyl phosphorothioate
  参考文献：
  名称：

  在热带和亚热带条件下，14C-杀14硫酮在紫外线和阳光的作用下分解。

  摘要：

  研究了在阳光和紫外线下硅胶色谱板上以及极性和非极性溶剂中（14）C-杀fe硫酮在豆类植物叶片表面和不同表面（例如玻璃，石英）上对太阳光的稳定性。和塑料）也被确定。鉴定出主要的光产物为羧基杀nitro硫磷，杀nitro磷，杀fe磷和3-甲基-4-硝基苯酚以及少量的3-羧基-4-硝基苯酚和甲基对硫磷。西维因和溴氰菊酯类杀虫剂的加入略微加快了杀nitro硫酮在硅胶板上和溶液中的光分解。

  DOI：

  10.1016/j.chemosphere.2007.07.063

文献信息

• Unequivocal Identification of Compounds Formed in the Photodegradation of Fenitrothion in Water/Methanol and Proposal of Selected Transformation Pathways
  作者：G. Durand、J. L. Abad、F. Sanchez-Baeza、A. Messeguer、D. Barcelo

  DOI：10.1021/jf00039a044

  日期：1994.3

  The photodegradation of fenitrothion was examined in a mixture of distilled water/methanol (5:1), The UV irradiation was carried out with a high-pressure Hg lamp during 7 h. For the identification of further breakdown products, fenitrooxon and carboxyfenitrothion were also irradiated under experimental conditions identical to those for fenitrothion. The identification of the breakdown products formed was carried out by gas chromatography-mass spectrometry (GC-MS) with electron impact (EI) and comparison with authentic standards synthesized in the laboratory. A total of 21 photoproducts of oxidation, isomerization, denitration, and solvolysis that may be of concern in environmental studies were unequivocally identified. Among them were formyldenitrofenitrothion, carbomethoxydenitro-fenitrooxon, and hydroxymethyldenitrofenitrooxon. A proposed mechanism of the process is presented. Selected pathways for the photodegradation of fenitrothion were examined: (i) degradation through hydrolysis, with eventual remethylation; (ii) P=S to P=O oxidation; (iii) denitration; and (iv) oxidation of the methyl substituent through hydroxymethyl and formyl to give the corresponding carboxy derivatives.
• Decomposition of 14C-fenitrothion under the influence of UV and sunlight under tropical and subtropical conditions
  作者：S.M.A.D. Zayed、F. Mahdy

  DOI：10.1016/j.chemosphere.2007.07.063

  日期：2008.2

  ultraviolet light was investigated, Its stability to sunlight on leaf surfaces of bean plants and on different surfaces (such as glass, quartz and plastic) was also determined. The main photoproducts were identified as carboxyfenitrothion, fenitrooxon, carboxyfenitrooxon and 3-methyl-4-nitrophenol and a small amount 3-caboxy-4-nitrophenol and methyl parathion. The addition of carbaryl and deltamethrin

  研究了在阳光和紫外线下硅胶色谱板上以及极性和非极性溶剂中（14）C-杀fe硫酮在豆类植物叶片表面和不同表面（例如玻璃，石英）上对太阳光的稳定性。和塑料）也被确定。鉴定出主要的光产物为羧基杀nitro硫磷，杀nitro磷，杀fe磷和3-甲基-4-硝基苯酚以及少量的3-羧基-4-硝基苯酚和甲基对硫磷。西维因和溴氰菊酯类杀虫剂的加入略微加快了杀nitro硫酮在硅胶板上和溶液中的光分解。