2,3-bis(pentafluorobenzyl)pyrenedicarboxylate | 137300-28-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 2,3-bis(pentafluorobenzyl)pyrenedicarboxylate
• 英文别名: Bis[(pentafluorophenyl)methyl] pyrene-1,2-dicarboxylate；bis[(2,3,4,5,6-pentafluorophenyl)methyl] pyrene-1,2-dicarboxylate
• CAS: 137300-28-8
• 化学式: C₃₂H₁₂F₁₀O₄
• 分子量: 650.429
• InChiKey: TYXOTOKDHSMAII-UHFFFAOYSA-N

物化性质

• 沸点：
  617.1±50.0 °C(Predicted)
• 密度：
  1.620±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  46
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  苯并[a]芘 、 α-溴-2,3,4,5,6-五氟甲基苯酸酯 在 18-冠醚-6 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 26.0h， 以0.14%的产率得到2,3-bis(pentafluorobenzyl)pyrenedicarboxylate
  参考文献：
  名称：

  Polar Forms of Benzo[a]pyrene May Be Ubiquitous in the Environment

  摘要：

  Previously, we reported that polar polycyclic aromatic compounds (polar PAC) can be detected by first oxidizing them with KO2/O-2 and then detecting the carboxylic acid products, after pentafluorobenzylation, by gas chromatography electron capture mass spectrometry (Allam et at. Anal. Chem. 1992, 65, 1723-1727). For example, we used the method in the cited study to detect a benzo[a]pyrene tetrahydrotetraol hydrolysis product derived from benzo[a]pyrene-exposed lymphocytes after isolation of the DNA. However,the method was limited in its sensitivity by the presence of an interfering, analyte-like peak in the final mass chromatograms. Now, the results of our current work strong ly suggest that the contamination leading to the unwanted peak is ubiquitous in the urban environment. Results from the analysis of a standard reference sample of urban particulate matter (SRM 1649) yielded a level of 10 ng of contaminant in a 5-mg sample (2 mu g/g). The concentration of this polar contaminant is comparable to the certified value for benzo[a]pyrene of 14.5 ng (2.9 mu g/g). Furthermore, our mass spectral data show evidence for the presence of many other polar PAC in the sample. These observations add to the concern raised by related environmental health studies focused on the potential impact of airborne polar PAC on human health.

  DOI：

  10.1021/es9710722

文献信息

• Polar Forms of Benzo[<i>a</i>]pyrene May Be Ubiquitous in the Environment
  作者：Yasser Ismail、Arthur L. Lafleur、Roger W. Giese

  DOI：10.1021/es9710722

  日期：1998.9.1

  Previously, we reported that polar polycyclic aromatic compounds (polar PAC) can be detected by first oxidizing them with KO2/O-2 and then detecting the carboxylic acid products, after pentafluorobenzylation, by gas chromatography electron capture mass spectrometry (Allam et at. Anal. Chem. 1992, 65, 1723-1727). For example, we used the method in the cited study to detect a benzo[a]pyrene tetrahydrotetraol hydrolysis product derived from benzo[a]pyrene-exposed lymphocytes after isolation of the DNA. However,the method was limited in its sensitivity by the presence of an interfering, analyte-like peak in the final mass chromatograms. Now, the results of our current work strong ly suggest that the contamination leading to the unwanted peak is ubiquitous in the urban environment. Results from the analysis of a standard reference sample of urban particulate matter (SRM 1649) yielded a level of 10 ng of contaminant in a 5-mg sample (2 mu g/g). The concentration of this polar contaminant is comparable to the certified value for benzo[a]pyrene of 14.5 ng (2.9 mu g/g). Furthermore, our mass spectral data show evidence for the presence of many other polar PAC in the sample. These observations add to the concern raised by related environmental health studies focused on the potential impact of airborne polar PAC on human health.