methyl chloroiodoacetate | 53235-05-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl chloroiodoacetate
• 英文别名: Methyl-iod-chlor-acetat；Methylchloriodacetat；Acetic acid, chloroiodo-, methyl ester；methyl 2-chloro-2-iodoacetate
• CAS: 53235-05-5
• 化学式: C₃H₄ClIO₂
• 分子量: 234.421
• InChiKey: PNAAWBJWSUNQPD-UHFFFAOYSA-N

物化性质

• 沸点：
  193.8±20.0 °C(Predicted)
• 密度：
  2.090±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl chloroiodoacetate 在 ammonium hydroxide 作用下， 生成 chloroiodoacetamide
  参考文献：
  名称：

  Occurrence, Synthesis, and Mammalian Cell Cytotoxicity and Genotoxicity of Haloacetamides: An Emerging Class of Nitrogenous Drinking Water Disinfection Byproducts

  摘要：

  The haloacetamides, a class of emerging nitrogenous drinking water disinfection byproduct (DBPs), were analyzed for their chronic cytotoxicity and for the induction of genomic DNA damage in Chinese hamster ovary cells. The rank order for cytotoxicity of 13 haloacetamides was DIAcAm > IAcAm > BAcAm > TBAcAm > BIAcAm > DBCAcAm > CIAcAm > BDCAcAm > DBAcAm > BCAcAm > CAcAm > DCAcAm > TCAcAm. The rank order of their genotoxicity was TBAcAm > DIAcAm IAcAm > BAcAm > DBCAcAm > BIAcAm > BDCAcAm > CIAcAm > BCAcAm > DBAcAm > CAcAm > TCAcAm. DCAcAm was not genotoxic. Cytotoxicity and genotoxicity were primarily determined by the leaving tendency of the halogens and followed the order I > Br > > CI. With the exception of brominated trihaloacetamides, most of the toxicity rank order was consistent with structure-activity relationship expectations. For di- and trihaloacetamides, the presence of at least one good leaving halogen group (I or Br but not CI) appears to be critical for significant toxic activity. Log P was not a factor for monohaloacetamides but may play a role in the genotoxicity of trihaloacetamides and possible activation of dihaloacetamides by intracellular GSH and -SH compounds. With the advent of the U.S. EPA Stage 2 DBP regulations, water utilities are considering the use of disinfectants that are alternatives to chlorine. The use of these alternative disinfectants will shift the distribution of DBP chemical classes. The emergence of new, highly toxic iodinated, nitrogenous DBPs, as illustrated by the discovery of bromoiodoacetamide as a new DBP, underscores the importance of comparative toxicity studies to assist in the overall goal of safer drinking water practice.

  DOI：

  10.1021/es071754h
• 作为产物：
  描述：

  二氯乙酸甲酯 在 potassium iodide 作用下， 以 丙酮 为溶剂， 生成 methyl chloroiodoacetate
  参考文献：
  名称：

  卤甲基金属化合物：LXIX。某些功能卤代甲基汞化合物的制备

  摘要：

  有机汞试剂PhHgCCl 2 SO 2 Ph，PhHgCBr 2 SO 2 Ph，PhHgCClICO 2 Me，环-C 6 H 11 HgCCl 2 CO 2 Me，PhCH 2 CH 2 HgCCl 2 CO 2 Me，PhHgCHClCO 2 -Et和PhHgCCl 2 CONMe 2已经制备了它们，并研究了它们作为二价碳转移试剂的应用。

  DOI：

  10.1016/s0022-328x(00)95166-0

文献信息

• Occurrence, Synthesis, and Mammalian Cell Cytotoxicity and Genotoxicity of Haloacetamides: An Emerging Class of Nitrogenous Drinking Water Disinfection Byproducts
  作者：Michael J. Plewa、Mark G. Muellner、Susan D. Richardson、Francesca Fasano、Katherine M. Buettner、Yin-Tak Woo、A. Bruce McKague、Elizabeth D. Wagner

  DOI：10.1021/es071754h

  日期：2008.2.1

  The haloacetamides, a class of emerging nitrogenous drinking water disinfection byproduct (DBPs), were analyzed for their chronic cytotoxicity and for the induction of genomic DNA damage in Chinese hamster ovary cells. The rank order for cytotoxicity of 13 haloacetamides was DIAcAm > IAcAm > BAcAm > TBAcAm > BIAcAm > DBCAcAm > CIAcAm > BDCAcAm > DBAcAm > BCAcAm > CAcAm > DCAcAm > TCAcAm. The rank order of their genotoxicity was TBAcAm > DIAcAm IAcAm > BAcAm > DBCAcAm > BIAcAm > BDCAcAm > CIAcAm > BCAcAm > DBAcAm > CAcAm > TCAcAm. DCAcAm was not genotoxic. Cytotoxicity and genotoxicity were primarily determined by the leaving tendency of the halogens and followed the order I > Br > > CI. With the exception of brominated trihaloacetamides, most of the toxicity rank order was consistent with structure-activity relationship expectations. For di- and trihaloacetamides, the presence of at least one good leaving halogen group (I or Br but not CI) appears to be critical for significant toxic activity. Log P was not a factor for monohaloacetamides but may play a role in the genotoxicity of trihaloacetamides and possible activation of dihaloacetamides by intracellular GSH and -SH compounds. With the advent of the U.S. EPA Stage 2 DBP regulations, water utilities are considering the use of disinfectants that are alternatives to chlorine. The use of these alternative disinfectants will shift the distribution of DBP chemical classes. The emergence of new, highly toxic iodinated, nitrogenous DBPs, as illustrated by the discovery of bromoiodoacetamide as a new DBP, underscores the importance of comparative toxicity studies to assist in the overall goal of safer drinking water practice.
• Halomethylmetal compounds
  作者：Dietmar Seyferth、Robert A. Woodruff

  DOI：10.1016/s0022-328x(00)95166-0

  日期：1974.5

  The organomercury reagents PhHgCCl2SO2Ph, PhHgCBr2SO2Ph, PhHgCClICO2Me, cyclo-C6H11HgCCl2CO2Me, PhCH2CH2HgCCl2CO2Me, PhHgCHClCO2-Et and PhHgCCl2CONMe2 have been prepared and their application as divalent carbon transfer reagents has been examined.

  有机汞试剂PhHgCCl 2 SO 2 Ph，PhHgCBr 2 SO 2 Ph，PhHgCClICO 2 Me，环-C 6 H 11 HgCCl 2 CO 2 Me，PhCH 2 CH 2 HgCCl 2 CO 2 Me，PhHgCHClCO 2 -Et和PhHgCCl 2 CONMe 2已经制备了它们，并研究了它们作为二价碳转移试剂的应用。