溴二氯乙酸甲酯 | 20428-76-6

• 物质功能分类: 分析化学 - 标准品 - 挥发性有机化合物(VOCs)
• 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: 溴二氯乙酸甲酯
• 中文别名: 一溴二氯乙酸甲酯
• 英文名称: bromodichloroacetic acid methyl ester
• 英文别名: Dichlorbromessigsaeure-methylester；Methyl bromodichloroacetate；methyl 2-bromo-2,2-dichloroacetate
• CAS: 20428-76-6
• 化学式: C₃H₃BrCl₂O₂
• 分子量: 221.866
• InChiKey: VCMGKXLUCUYXBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  8
• 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

安全信息

• 危险品标志：
  F,Xi
• 安全说明：
  S16,S26,S36
• 危险类别码：
  R40,R36/37/38,R38
• WGK Germany：
  1
• 危险品运输编号：
  UN 2398 3/PG 2
• 海关编码：
  2905199090

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  一溴二氯乙酸	bromodichloroacetic acid	71133-14-7	C2HBrCl2O2	207.839
  二氯乙酸甲酯	dichloroacetic acid methyl ester	116-54-1	C3H4Cl2O2	142.97

反应信息

• 作为反应物：
  描述：

  溴二氯乙酸甲酯 在 ammonium hydroxide 作用下， 生成 溴代氯乙酰胺
  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：

  二氯乙酸甲酯 在 三溴化磷 、 copper(I) bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以35.5 %的产率得到溴二氯乙酸甲酯
  参考文献：
  名称：

  CN116023261

  摘要：

  公开号：

文献信息

• In Situ Derivatization/Solid-Phase Microextraction for the Determination of Haloacetic Acids in Water
  作者：M. N. Sarrión、F. J. Santos、M. T. Galceran

  DOI：10.1021/ac000479d

  日期：2000.10.1

  An in situ derivatization solid-phase microextraction method has been developed for the determination of haloacetic acids (HAAs) in water. The analytical procedure involves derivatization of HAAs to their methyl esters with dimethyl sulfate, headspace sampling using solid-phase microextraction (SPME), and gas chromatography-ion trap mass spectrometry (GC/ITMS) determination. Parameters affecting both derivatization efficiency and headspace SPME procedure, such as the selection of the SPME coating, derivatization−extraction time and temperature, and ionic strength, were optimized. The commercially available Carboxen-poly(dimethylsiloxane) (CAR-PDMS) fiber appears to be the most suitable for the determination of HAAs. Moreover, the formation of HAA methyl esters was dramatically improved (up to 90-fold) by the addition of tetrabutylammonium hydrogen sulfate (4.7 μmol) to the sample as ion-pairing agent in the derivatization step. The precision of the in situ derivatization/HS-SPME/GC/ITMS method evaluated using an internal standard gave relative standard deviations (RSDs) between 6.3 and 11.4%. The method was linear over 2 orders of magnitude, and detection limits were compound-dependent, but ranged from 10 to 450 ng/L. The method was compared with the EPA method 552.2 for the analysis of HAAs in various water samples, and good agreement was obtained. Consequently, in situ derivatization/HS-SPME/GC/ITMS is proposed for the analysis of HAAs in water.

  开发了一种原位衍生化固相微萃取方法，用于水中卤乙酸（HAAs）的测定。分析过程涉及HAAs与二甲基硫酸酯衍生化为甲酯，使用固相微萃取（SPME）进行顶空采样，以及采用气相色谱-离子阱质谱（GC/ITMS）进行测定。优化了影响衍生化效率和顶空SPME过程的参数，如SPME涂层的选择、衍生化-萃取时间与温度以及离子强度等。市售的Carboxen-聚（二甲基硅氧烷）（CAR-PDMS）纤维似乎最适合于HAAs的测定。此外，在衍生化步骤中，向样品中添加四丁基硫酸氢铵（4.7 μmol）作为离子配对剂，显著提高了HAA甲酯的形成（高达90倍）。使用内标法评估的原位衍生化/HS-SPME/GC/ITMS方法的精密度给出了相对标准偏差（RSDs）在6.3%至11.4%之间。该方法在线性范围超过2个数量级，检出限因化合物而异，但范围在10至450 ng/L之间。该方法与EPA方法552.2针对各种水样中HAAs的分析进行了比较，得到了良好的一致性。因此，提出原位衍生化/HS-SPME/GC/ITMS用于水中HAAs的分析。
• Koebrich,G.; Fischer,R.H., Chemische Berichte, 1968, vol. 101, p. 3219 - 3229
  作者：Koebrich,G.、Fischer,R.H.

  DOI：——

  日期：——
• 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.
• CN116023261
  申请人：——

  公开号：——

  公开（公告）日：——