一溴一氯硝基甲烷 | 135531-25-8

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 一溴一氯硝基甲烷
• 中文别名: 溴(氯)硝基甲烷
• 英文名称: bromochloronitromethane
• 英文别名: bromo-chloro-nitromethane
• CAS: 135531-25-8
• 化学式: CHBrClNO₂
• 分子量: 174.381
• InChiKey: QUGLTGHXUDTPKJ-UHFFFAOYSA-N

物化性质

• 沸点：
  132.7±20.0 °C(Predicted)
• 密度：
  2.106±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少量）、DMSO（少量）、甲醇（少量）

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

制备方法与用途

生物活性方面，溴氯硝基甲烷（Bromochloronitromethane）属于卤代硝基甲烷类化合物，是饮用水中的一种消毒副产物。

反应信息

• 作为产物：
  描述：

  methyl bromochloronitroacetate 在 硫酸 作用下， 反应 3.0h， 生成 一溴一氯硝基甲烷
  参考文献：
  名称：

  Halonitromethane Drinking Water Disinfection Byproducts:  Chemical Characterization and Mammalian Cell Cytotoxicity and Genotoxicity

  摘要：

  Halonitromethanes are drinking water disinfection byproducts that have recently received a high priority for health effects research from the U.S. Environmental Protection Agency (EPA). Our purpose was to identify and synthesize where necessary the mixed halonitromethanes and to determine the chronic cytotoxicity and the acute genotoxicity of these agents in mammalian cells. The halonitromethanes included bromonitromethane (BNM), dibromonitromethane (DBNM), tribromonitromethane (TBNM), bromochloronitromethane (BCNM), dibromochloronitromethane (DBCNM), bromodichloronitromethane (BDCNM), chloronitromethane (CNM), dichloronitromethane (DCNM), and trichloronitromethane (TCNM). Low- and high-resolution gas chromatography/mass spectrometry (GC/MS) was used to identify the mixed chloro-bromo nitromethanes in finished drinking waters, and analytical standards that were not commercially available were synthesized (BDCNM, DBCNM, TBNM, CNM, DCNM, BCNM). The rank order of their chronic cytotoxicity (72 h exposure) to Chinese hamster ovary (CHO) cells was DBNM > DBCNM > BNM > TBNM > BDCNM > BCNM > DCNM > CNM > TCNM. The rank order to induce genomic DNA damage in CHO cells was DBNM > BDCNM > TBNM > TCNM > BNM > DBCNM > BCNM > DCNM > CNM. The brominated nitromethanes were more cytotoxic and genotoxic than their chlorinated analogues. This research demonstrated the integration of the procedures for the analytical chemistry and analytical biology when working with limited amounts of sample. The halonitromethanes are potent mammalian cell cytotoxins and genotoxins and may pose a hazard to the public health and the environment.

  DOI：

  10.1021/es030477l