2-Chloro-4-(3-chloro-4-nitrophenyl)aniline | 413567-75-6

• 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: 2-Chloro-4-(3-chloro-4-nitrophenyl)aniline
• CAS: 413567-75-6
• 化学式: C₁₂H₈Cl₂N₂O₂
• 分子量: 283.114
• InChiKey: FNYYXQKTOLJOEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Chloro-4-(3-chloro-4-nitrophenyl)aniline 在 盐酸 、 氧气 、 二氧化氮 、 臭氧 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 0.17h， 生成 4-amino-3,3'-dichloro-5,4'-dinitrobiphenyl
  参考文献：
  名称：

  Identification of a New Mutagenic Polychlorinated Biphenyl Derivative in the Waka River, Wakayama, Japan, Showing Activation of an Aryl Hydrocarbon Receptor-Dependent Transcription

  摘要：

  Water samples from the Waka River, which runs through an area housing many chemical industry facilities in Wakayama, Japan, have been found to show significant mutagenicity, especially without a mammalian metabolic activation system (S9 mix) in the Salmonella typhimuirium YG1024 strain. Mutagens in the river water were adsorbed to 3 kg of blue cotton, extracted with methanol/ammonia, and separated by several low- and high-pressure liquid chromatography steps with reversed-phase columns, One mutagen (0.6 mg), accounting for 50% of the total mutagenicity of the adsorbed materials, was isolated. On the basis of the mass, high-resolution mass, H-1 NMR and C-13 NMR spectra, the chemical was determined to have a polychlorinated biphenyl skeleton with nitro and amino substitution groups. Well-designed chemical synthesis of the putative mutagen revealed it to be 4-amino-3,3'-dichloro-5,4'-dinitrobiphenyt. This novel compound exerted strong mutagenicity without the S9 mix, inducing 66 000 and 140 000 revertants/nmol in S. typhimurium TA98 and YG1024, respectively. Moreover, this polychlorinated biphenyl derivative was proven to activate the human aryl hydrocarbon receptor-mediated transcription in a lac Z reporter gene assay with an efficiency almost the same as that of beta-naphthoflavone, well-known to be a synthetic aryl hydrocarbon receptor agonist. It is possible that the mutagen is formed unintentionally via postemission modification of drainage water containing parent chemicals, such as 3,3'-dichlorobenzidine or 3,3'-dichloro-4,4'-dinitrobiphenyl, which are known to be raw materials in the manufacture of polymers and dye intermediates in chemical plants.

  DOI：

  10.1021/tx010163g
• 作为产物：
  描述：

  3,3′-二氯联苯胺 在 sodium hydrogensulfide 、 双氧水 、 溶剂黄146 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 10.0h， 生成 2-Chloro-4-(3-chloro-4-nitrophenyl)aniline
  参考文献：
  名称：

  Identification of a New Mutagenic Polychlorinated Biphenyl Derivative in the Waka River, Wakayama, Japan, Showing Activation of an Aryl Hydrocarbon Receptor-Dependent Transcription

  摘要：

  Water samples from the Waka River, which runs through an area housing many chemical industry facilities in Wakayama, Japan, have been found to show significant mutagenicity, especially without a mammalian metabolic activation system (S9 mix) in the Salmonella typhimuirium YG1024 strain. Mutagens in the river water were adsorbed to 3 kg of blue cotton, extracted with methanol/ammonia, and separated by several low- and high-pressure liquid chromatography steps with reversed-phase columns, One mutagen (0.6 mg), accounting for 50% of the total mutagenicity of the adsorbed materials, was isolated. On the basis of the mass, high-resolution mass, H-1 NMR and C-13 NMR spectra, the chemical was determined to have a polychlorinated biphenyl skeleton with nitro and amino substitution groups. Well-designed chemical synthesis of the putative mutagen revealed it to be 4-amino-3,3'-dichloro-5,4'-dinitrobiphenyt. This novel compound exerted strong mutagenicity without the S9 mix, inducing 66 000 and 140 000 revertants/nmol in S. typhimurium TA98 and YG1024, respectively. Moreover, this polychlorinated biphenyl derivative was proven to activate the human aryl hydrocarbon receptor-mediated transcription in a lac Z reporter gene assay with an efficiency almost the same as that of beta-naphthoflavone, well-known to be a synthetic aryl hydrocarbon receptor agonist. It is possible that the mutagen is formed unintentionally via postemission modification of drainage water containing parent chemicals, such as 3,3'-dichlorobenzidine or 3,3'-dichloro-4,4'-dinitrobiphenyl, which are known to be raw materials in the manufacture of polymers and dye intermediates in chemical plants.

  DOI：

  10.1021/tx010163g

文献信息

• Identification of a New Mutagenic Polychlorinated Biphenyl Derivative in the Waka River, Wakayama, Japan, Showing Activation of an Aryl Hydrocarbon Receptor-Dependent Transcription
  作者：Takeji Takamura-Enya、Tetsushi Watanabe、Atsuko Tada、Teruhisa Hirayama、Haruo Nukaya、Takashi Sugimura、Keiji Wakabayashi

  DOI：10.1021/tx010163g

  日期：2002.3.1

  Water samples from the Waka River, which runs through an area housing many chemical industry facilities in Wakayama, Japan, have been found to show significant mutagenicity, especially without a mammalian metabolic activation system (S9 mix) in the Salmonella typhimuirium YG1024 strain. Mutagens in the river water were adsorbed to 3 kg of blue cotton, extracted with methanol/ammonia, and separated by several low- and high-pressure liquid chromatography steps with reversed-phase columns, One mutagen (0.6 mg), accounting for 50% of the total mutagenicity of the adsorbed materials, was isolated. On the basis of the mass, high-resolution mass, H-1 NMR and C-13 NMR spectra, the chemical was determined to have a polychlorinated biphenyl skeleton with nitro and amino substitution groups. Well-designed chemical synthesis of the putative mutagen revealed it to be 4-amino-3,3'-dichloro-5,4'-dinitrobiphenyt. This novel compound exerted strong mutagenicity without the S9 mix, inducing 66 000 and 140 000 revertants/nmol in S. typhimurium TA98 and YG1024, respectively. Moreover, this polychlorinated biphenyl derivative was proven to activate the human aryl hydrocarbon receptor-mediated transcription in a lac Z reporter gene assay with an efficiency almost the same as that of beta-naphthoflavone, well-known to be a synthetic aryl hydrocarbon receptor agonist. It is possible that the mutagen is formed unintentionally via postemission modification of drainage water containing parent chemicals, such as 3,3'-dichlorobenzidine or 3,3'-dichloro-4,4'-dinitrobiphenyl, which are known to be raw materials in the manufacture of polymers and dye intermediates in chemical plants.