2-溴-2-氯乙酸乙酯 | 22524-32-9

• 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: 2-溴-2-氯乙酸乙酯
• 英文名称: ethyl 2-bromo-2-chloroacetate
• 英文别名: Chlor-bromessigsaeureaethylester；Brom-chloressigsaeureethylester；bromo-chloro-acetic acid ethyl ester；Brom-chlor-essigsaeure-aethylester
• CAS: 22524-32-9
• 化学式: C₄H₆BrClO₂
• 分子量: 201.447
• InChiKey: ROKCSLROOSHJSM-UHFFFAOYSA-N

物化性质

• 密度：
  1.5890

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  2-溴-2-氯乙酸乙酯 在 氨 、 水 作用下， 生成 一溴一氯乙酰胺
  参考文献：
  名称：

  Cech; Steiner, Chemische Berichte, 1875, vol. 8, p. 1174

  摘要：

  DOI：
• 作为产物：
  描述：

  重氮乙酸乙酯 在 copper(II) bis(trifluoromethanesulfonate) 、 tetrabutylammonium dichlorobromate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以75%的产率得到2-溴-2-氯乙酸乙酯
  参考文献：
  名称：

  Tetrabutylammonium dichlorobromide: an efficient and mild reagent for geminal bromochlorination of α-diazo carbonyl compounds

  摘要：

  An efficient and mild one-pot procedure for geminal bromochlorination of alpha-diazo carbonyl compounds has been developed for the first time using tetrabutylammonium dichlorobromide (TBADCB) via metal carbenoids. This protocol was found to be highly selective and does not result in dichlorination or dibromination products. The reagent, TBADCB, is commercially available, easy to prepare and handle. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.12.117

文献信息

• 一种唑来膦酸中间体化合物
  申请人：鲁南制药集团股份有限公司

  公开号：CN112574113A

  公开（公告）日：2021-03-30

  本发明属于医药合成技术领域，具体涉及一种唑来膦酸中间体化合物。本发明以2,2‑双取代乙酸酯和咪唑为起始原料，经过取代反应、水解反应合成2,2‑咪唑乙酸盐酸盐中间体，该方法原料简单易得，反应条件温和，操作过程简便，经济环保；利用该中间体化合物制备的唑来膦酸收率可达到85.27％，且无双膦酸杂质，纯度高达99.8％以上。
• 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.
• Preparation of Triazines by the Reaction of Biguanide and Esters¹
  作者：C. G. Overberger、Francis W. Michelotti、Philip M. Carabateas

  DOI：10.1021/ja01561a044

  日期：1957.2
• CCXIV.—Dichloroacetates and chlorobromoacetates from αβ-dichlorovinyl ethyl ether
  作者：Holland Crompton、Phyllis Mary Triffitt

  DOI：10.1039/ct9211901874

  日期：——
• Smith, Journal of the Chemical Society, 1927, p. 1101
  作者：Smith

  DOI：——

  日期：——