Chloronitroacetic acid methyl ester | 82208-51-3

• 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: Chloronitroacetic acid methyl ester
• 英文别名: methyl chloronitroacetate；Chlor-nitro-essigsaeure-methylester；methyl 2-chloro-2-nitroacetate
• CAS: 82208-51-3
• 化学式: C₃H₄ClNO₄
• 分子量: 153.522
• InChiKey: ILDQLKIDLMWEMK-UHFFFAOYSA-N

物化性质

• 沸点：
  25 °C(Press: 0.2 Torr)
• 密度：
  1.4536 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  9
• 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：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Chloronitroacetic acid methyl ester 反应 20.0h， 以0.81 g的产率得到草酸铵甲酯
  参考文献：
  名称：

  Decomposition products of halonitroacetic acid derivatives

  摘要：

  The halonitro group O2NCHX of chloro- and bromonitroacetic acid derivatives underwent reduction to H2NCO upon boiling. The same derivatives decomposed to oxalic acid upon long storage. Likely chemical transformation pathways are discussed.

  DOI：

  10.1007/bf00863925
• 作为产物：
  描述：

  2-氯-3-羟基-2-硝基丙酸甲酯 在 sodium dichromate 、 硫酸 作用下， 生成 Chloronitroacetic acid methyl ester
  参考文献：
  名称：

  Martynov,I.V. et al., Journal of general chemistry of the USSR, 1963, vol. 33, p. 3308 - 3310

  摘要：

  DOI：

文献信息

• Martynov, I. V.; Postnova, L. V.; Bikkineev, R. Kh., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, # 8, p. 1571 - 1573
  作者：Martynov, I. V.、Postnova, L. V.、Bikkineev, R. Kh.、Yurtanov, A. I.

  DOI：——

  日期：——
• Reduction of chloro-and bromonitroacetate esters
  作者：A. I. Yurtanov、E. S. Naidovskii、Yu. P. Belov、I. V. Martynov

  DOI：10.1007/bf00956377

  日期：1987.5
• Halonitromethane Drinking Water Disinfection Byproducts:  Chemical Characterization and Mammalian Cell Cytotoxicity and Genotoxicity
  作者：Michael J. Plewa、Elizabeth D. Wagner、Paulina Jazwierska、Susan D. Richardson、Paul H. Chen、A. Bruce McKague

  DOI：10.1021/es030477l

  日期：2004.1.1

  Halonitromethanes are drinking water disinfection byproducts that have recently received a high priority for health effects research from the U.S. Environmental Protection Agency (EPA). Our purpose was to identify and synthesize where necessary the mixed halonitromethanes and to determine the chronic cytotoxicity and the acute genotoxicity of these agents in mammalian cells. The halonitromethanes included bromonitromethane (BNM), dibromonitromethane (DBNM), tribromonitromethane (TBNM), bromochloronitromethane (BCNM), dibromochloronitromethane (DBCNM), bromodichloronitromethane (BDCNM), chloronitromethane (CNM), dichloronitromethane (DCNM), and trichloronitromethane (TCNM). Low- and high-resolution gas chromatography/mass spectrometry (GC/MS) was used to identify the mixed chloro-bromo nitromethanes in finished drinking waters, and analytical standards that were not commercially available were synthesized (BDCNM, DBCNM, TBNM, CNM, DCNM, BCNM). The rank order of their chronic cytotoxicity (72 h exposure) to Chinese hamster ovary (CHO) cells was DBNM > DBCNM > BNM > TBNM > BDCNM > BCNM > DCNM > CNM > TCNM. The rank order to induce genomic DNA damage in CHO cells was DBNM > BDCNM > TBNM > TCNM > BNM > DBCNM > BCNM > DCNM > CNM. The brominated nitromethanes were more cytotoxic and genotoxic than their chlorinated analogues. This research demonstrated the integration of the procedures for the analytical chemistry and analytical biology when working with limited amounts of sample. The halonitromethanes are potent mammalian cell cytotoxins and genotoxins and may pose a hazard to the public health and the environment.
• Substitution of halogen atom in ?-halonitro compounds of the aliphatic series
  作者：A. I. Yurtanov、S. K. Baidildaeva、A. N. Chekhlov、N. S. Zefirov

  DOI：10.1007/bf00717345

  日期：1994.5

  Ethyl alpha-halo-alpha-nitropropionate and -butyrate were prepared by alkylating ammonium salts of ethyl bromo- and chloronitroacetates. The addition of alkyl acrylates to alkyl chloronitroacetates or their salts gives dialkyl alpha-chloro-alpha-nitroglutarates. Sodium salts of ethyl alpha-nitro-alpha-sulfo-beta-hydroxypropionate and -butyrate were obtained by the sulfo-dehalogenation of ethyl alpha-chloro-alpha-nitro-beta-hydroxypropionate and -butyrate with sodium dithionite. Esters of a-amino acid hydrochlorides were prepared by the reduction of alkyl alpha-chloro-alpha-nitrocarboxylates. The hydrogenation of alkyl nitrosulfoacetates leads to the corresponding disodium salts of alkyl aminodisulfoacetates and piperazine-2,5-dione.
• Replacement of halogen in ?-halonitro-compounds of the aliphatic series. 3. Preparation and properties of sodium salts of esters of nitrosulfoacetic acid
  作者：A. I. Yurtanov、A. V. Yarkov、T. I. Ignat'eva、V. O. Zavel'skii、B. K. Beznosko、O. V. Novikova、V. N. Semyonova、I. V. Martynov

  DOI：10.1007/bf00959883

  日期：1988.11