二溴氯乙酰胺 | 855878-13-6

• 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: 二溴氯乙酰胺
• 英文名称: dibromochloroacetamide
• 英文别名: 2,2-dibromo-2-chloroacetamide
• CAS: 855878-13-6
• 化学式: C₂H₂Br₂ClNO
• 分子量: 251.305
• InChiKey: MBEDDIHHCDUVJV-UHFFFAOYSA-N

物化性质

• 沸点：
  247.1±40.0 °C(Predicted)
• 密度：
  2.509±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  7
• 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：
  43.1
• 氢给体数：
  1
• 氢受体数：
  1

制备方法与用途

生物活性方面，二溴氯甲酸（Dibromochloroacetamide）属于溴代卤代乙酰胺类化合物，是一种在饮用水消毒过程中形成的副产品。

反应信息

• 作为反应物：
  描述：

  二溴氯乙酰胺 、 硫酸 、 水 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Levy; Jedlicka, Justus Liebigs Annalen der Chemie, 1888, vol. 249, p. 86

  摘要：

  DOI：
• 作为产物：
  描述：

  1,1,1,3,3-五溴-3-氯丙酮 在 ammonium hydroxide 作用下， 以 乙醚 为溶剂， 生成 二溴氯乙酰胺
  参考文献：
  名称：

  Perhaloketones—XVII

  摘要：

  DOI：

  10.1016/s0040-4020(01)82752-6

文献信息

• Neumeister, Chemische Berichte, 1882, vol. 15, p. 602
  作者：Neumeister

  DOI：——

  日期：——
• Hydrolysis of haloacetonitriles: LINEAR FREE ENERGY RELATIONSHIP, kinetics and products
  作者：Victor Glezer、Batsheva Harris、Nelly Tal、Berta Iosefzon、Ovadia Lev

  DOI：10.1016/s0043-1354(98)00361-3

  日期：1999.6

  The hydrolysis rates of mono-, di- and trihaioacetonitriles were studied in aqueous buffer solutions at different pH. The stability of haloacetonitriles decreases and the hydrolysis rate increases with increasing pH and number of halogen atoms in the molecule: The monochloroacetonitriles are the most stable and are also less affected by pH-changes, while the trihaloacetonitriles are the least stable and most sensitive to pH changes. The stability of haloacetonitriles also increases by substitution of chlorine atoms with bromine atoms. The hydrolysis rates in different buffer solutions follow first order kinetics with a minimum hydrolysis rate at intermediate pH. Thus, haloacetonitriles have to be preserved in weakly acid solutions between sampling and analysis. The corresponding haloacetamides are formed during hydrolysis and in basic solutions they can hydrolyze further to give haloacetic acids. Linear free energy relationship can be used for prediction of degradation of haloacetonitriles during hydrolysis in water solutions. (C) 1999 Elsevier Science Ltd. All rights reserved.
• 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.
• Zincke; Kegel, Chemische Berichte, 1890, vol. 23, p. 241
  作者：Zincke、Kegel

  DOI：——

  日期：——
• Zincke; Kegel, Chemische Berichte, 1890, vol. 23, p. 1720
  作者：Zincke、Kegel

  DOI：——

  日期：——