一溴一碘乙酸 | 71815-43-5

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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
• 中文名称: 一溴一碘乙酸
• 中文别名: 溴碘乙酸
• 英文名称: bromoiodoacetic acid
• 英文别名: BIAA；Bromiodessigsaeure；2-bromo-2-iodoacetic acid
• CAS: 71815-43-5
• 化学式: C₂H₂BrIO₂
• 分子量: 264.845
• InChiKey: PMJXOVYMFHLFDD-UHFFFAOYSA-N

物化性质

• 沸点：
  272.1±25.0 °C(Predicted)
• 密度：
  2.990±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

制备方法与用途

生物活性方面，溴碘乙酸是一种碘代卤代酸，并且它是饮用水消毒副产物（DBPs）中的一个组成部分。

反应信息

• 作为反应物：
  描述：

  一溴一碘乙酸 在 甲醇 、 三氟化硼 、 ammonium hydroxide 作用下， 生成 2,2-二溴代乙酰胺 、 二碘乙酰胺 、 一溴一碘乙酰胺
  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：

  二碘乙酸 在 溴 作用下， 以 水 为溶剂， 反应 2.5h， 生成 二溴乙酸 、 一溴一碘乙酸
  参考文献：
  名称：

  新发现的碘酸饮用水消毒副产物的化学和生物学特性。

  摘要：

  碘酸饮用水消毒副产物（DBPs）最近在饮用水中的溴化物/碘化物浓度很高的饮用水样品中被发现，并用氯胺消毒。本文的目的是报告饮用水样品中碘乙酸（IA）和其他碘酸的化学分析鉴定，以解决IA在鼠伤寒沙门氏菌和哺乳动物细胞中的细胞毒性和遗传毒性，并报告其结构功能分析。 IA及其氯化和溴化单卤代类似物。碘酸DBPs被鉴定为碘乙酸，溴碘乙酸，（Z）-和（E）-3-溴-3-碘丙酸，（E）-2-碘-3-甲基丁烯二酸。IA代表了高毒性饮用水污染物的新类别（碘酸DBP）。IA在鼠伤寒沙门氏菌中的细胞毒性为2。分别比溴乙酸（BA）和氯乙酸（CA）高9倍和53.5倍。在中国仓鼠卵巢（CHO）细胞中发现了类似的细胞毒性趋势。IA的效力分别比BA和CA高3.2倍和287.5倍。该等级次序还以其遗传毒性表示，IA在鼠伤寒沙门氏菌TA100菌株中的致突变性分别比BA和CA高2.6倍和523.3倍。在CHO细胞中，IA的遗传毒性比BA高2

  DOI：

  10.1021/es049971v

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.
• Chemical and Biological Characterization of Newly Discovered Iodoacid Drinking Water Disinfection Byproducts
  作者：Michael J. Plewa、Elizabeth D. Wagner、Susan D. Richardson、Alfred D. Thruston、Yin-Tak Woo、A. Bruce McKague

  DOI：10.1021/es049971v

  日期：2004.9.1

  The iodoacid DBPs were identified as iodoacetic acid, bromoiodoacetic acid, (Z)- and (E)-3-bromo-3-iodopropenoic acid, and (E)-2-iodo-3-methylbutenedioic acid. IA represents a new class (iodoacid DBPs) of highly toxic drinking water contaminants. The cytotoxicity of IA in S. typhimurium was 2.9x and 53.5x higher than bromoacetic acid (BA) and chloroacetic acid (CA), respectively. A similar trend was

  碘酸饮用水消毒副产物（DBPs）最近在饮用水中的溴化物/碘化物浓度很高的饮用水样品中被发现，并用氯胺消毒。本文的目的是报告饮用水样品中碘乙酸（IA）和其他碘酸的化学分析鉴定，以解决IA在鼠伤寒沙门氏菌和哺乳动物细胞中的细胞毒性和遗传毒性，并报告其结构功能分析。 IA及其氯化和溴化单卤代类似物。碘酸DBPs被鉴定为碘乙酸，溴碘乙酸，（Z）-和（E）-3-溴-3-碘丙酸，（E）-2-碘-3-甲基丁烯二酸。IA代表了高毒性饮用水污染物的新类别（碘酸DBP）。IA在鼠伤寒沙门氏菌中的细胞毒性为2。分别比溴乙酸（BA）和氯乙酸（CA）高9倍和53.5倍。在中国仓鼠卵巢（CHO）细胞中发现了类似的细胞毒性趋势。IA的效力分别比BA和CA高3.2倍和287.5倍。该等级次序还以其遗传毒性表示，IA在鼠伤寒沙门氏菌TA100菌株中的致突变性分别比BA和CA高2.6倍和523.3倍。在CHO细胞中，IA的遗传毒性比BA高2