3,3'-dichloro-4,4'-dinitro-biphenyl | 37989-84-7

• 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: 3,3'-dichloro-4,4'-dinitro-biphenyl
• 英文别名: 3,3'-Dichlor-4,4'-dinitro-biphenyl；2-Chloro-4-(3-chloro-4-nitrophenyl)-1-nitrobenzene
• CAS: 37989-84-7
• 化学式: C₁₂H₆Cl₂N₂O₄
• 分子量: 313.097
• InChiKey: GPEWLWUJPTXWAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 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：
  91.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,3'-dichloro-4,4'-dinitro-biphenyl 在 sodium hydrogensulfide 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 N-[2-chloro-4-(3-chloro-4-nitrophenyl)phenyl]acetamide
  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 双氧水 作用下， 以 甲醇 、 水 为溶剂， 反应 0.33h， 以66.28%的产率得到3,3'-dichloro-4,4'-dinitro-biphenyl
  参考文献：
  名称：

  Process for the preparation of high quality 3,3′,4,4′-tetraminobiphenyl

  摘要：

  本发明涉及一种制备高纯度高质量3,3′,4,4′-四氨基联苯(TAB)的方法，高产量。本发明还公开了一种制备3,3′,4,4′-四氨基联苯(TAB)的三步法：(1)使用50％的aq.H2O2氧化3,3′-二氯-4,4′-二氨基联苯(DCB)，(2)将所得的3,3′-二硝基-4,4′-二硝基联苯(DCDNB)进行氨解，(3)使用氯化亚锡和浓盐酸还原3,3′-二氨基-4,4′-二硝基联苯(DADNB)。

  公开号：

  US06835854B1

文献信息

• Process for the preparation of high quality 3,3′,4,4′-tetraminobiphenyl
  申请人：Council of Scientific and Industrial Research

  公开号：US06835854B1

  公开（公告）日：2004-12-28

  The present invention relates to a process for the preparation of pure high quality 3,3′, 4,4′-tetraminobiphenyl (TAB) in high yields. The present invention also discloses a process for the preparation of 3,3′,4,4′ tetraminobiphenyl (TAB) comprising a three step process: (1) oxidation 3,3′-dichloro 4,4′-diaminobiphenyl (DCB) with 50% aq. H2O2, (2) ammonolysis of the resulting 3,3′-dinitro 4,4′-dinitrobiphenyl (DCDNB) and (3) reduction of 3,3′-diamino-4,4′-dinitrobiphenyl (DADNB) with stannous chloride and concentrated hydrochloric acid.

  本发明涉及一种制备高纯度高质量3,3′,4,4′-四氨基联苯(TAB)的方法，高产量。本发明还公开了一种制备3,3′,4,4′-四氨基联苯(TAB)的三步法：(1)使用50％的aq.H2O2氧化3,3′-二氯-4,4′-二氨基联苯(DCB)，(2)将所得的3,3′-二硝基-4,4′-二硝基联苯(DCDNB)进行氨解，(3)使用氯化亚锡和浓盐酸还原3,3′-二氨基-4,4′-二硝基联苯(DADNB)。
• Liquid crystal aligning agent and aligning agent-applied liquid crystal display device
  申请人：JAPAN SYNTHETIC RUBBER CO., LTD.

  公开号：EP0503918A1

  公开（公告）日：1992-09-16

  A liquid crystal aligning agent containing a polymer selected from the group consisting of a polyamic acid having a steroidal skeleton and an imidized product thereof; and a liquid crystal display device to which the liquid crystal aligning agent is applied.

  一种液晶对准剂，含有选自具有甾体骨架的聚酰胺酸及其亚酰胺化产物的聚合物；以及一种涂有该液晶对准剂的液晶显示装置。
• 33. The replacement of the diazonium by the nitro-group. Part II. Extension of the method to nitronaphthylamines, benzidine, and 3 : 3′-dichlorobenzidine
  作者：Herbert H. Hodgson、Edward R. Ward

  DOI：10.1039/jr9470000127

  日期：——
• US728
  申请人：——

  公开号：——

  公开（公告）日：——
• PROCESS FOR THE PREPARATION OF HIGH QUALITY 3,3',4,4'-TETRAMINOBIPHENYL
  申请人：Council of Scientific and Industrial Research

  公开号：EP1727781B1

  公开（公告）日：2009-05-06