2,4-dinitro-6-hydroxybenzyl alcohol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,4-dinitro-6-hydroxybenzyl alcohol
• 英文别名: 2,4-Dinitro-6-hydroxybenzyl alcohol；2-(hydroxymethyl)-3,5-dinitrophenol
• 化学式: C₇H₆N₂O₆
• 分子量: 214.134
• InChiKey: YXRAFGQISPUZSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  132
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,4,6-三硝基甲苯 在 Myriophyllum aquaticum 作用下， 以 水 为溶剂， 反应 288.0h， 生成 2-氨基-4,6-二硝基甲苯 、 4-氨基-2,6-二硝基甲苯 、 2-氨基-4,6-二硝基苯甲酸 、 2,4-dinitro-6-hydroxybenzyl alcohol
  参考文献：
  名称：

  Characterization of Oxidation Products of TNT Metabolism in Aquatic Phytoremediation Systems of Myriophyllum aquaticum

  摘要：

  TNT transformation processes in sediment-free, "natural", aquatic phytoremediation systems of Myriophyllum aquaticum were investigated with specific interest in oxidation products. Extraction procedures combining liquid-liquid extractions and solid-phase extractions were developed for the isolation of the mostly acidic, oxidized TNT metabolites. Six compounds unique from the reduction products of TNT were isolated and characterized by UV-vis, H-1, and C-13 NMR spectroscopy, by mass spectroscopy, and by chemical synthesis where feasible. These compounds include 2-amino-4,6-dinitrobenzoic acid, 2,4-dinitro-6-hydroxy-benzyl alcohol, 2-N-acetoxyamino-4,6-dinitrobenzaldehyde, 2,4-dinitro-6-hydroxytoluene, and two binuclear metabolites unique from the customary azoxytetranitro-toluenes. The monoaryl compounds show clear evidence of oxidative transformations, methyl oxidation and/or aromatic hydroxylation. It is possible that oxidative transformation(s) preceded nitro reduction since studies on exposure of M. aquaticum to either 2-amino-4,6-dinitrotoluene or 4-amino-2,6-dinitrotoluene did not yield any of the oxidation products identified here. The accumulation of oxidation products was significant: 2-amino-4,6-dinitrobenzoic acid, 4.4%; 2,4-dinitro-6-hydroxy-benzyl alcohol, 8.1%; 2-N-acetoxyamino-4,6-dinitrobenzaldehyde, 7.8%; and, 2,4-dinitro-6-hydroxytoluene, 15.6%. The binuclear metabolites accounted for an estimated 5.6%. This study is the first direct evidence for oxidative transformations in aquatic phytoremediation systems.

  DOI：

  10.1021/es990436i

文献信息

• Characterization of Oxidation Products of TNT Metabolism in Aquatic Phytoremediation Systems of <i>Myriophyllum</i> <i>aquaticum</i>
  作者：R. Bhadra、R. J. Spanggord、D. G. Wayment、J. B. Hughes、J. V. Shanks

  DOI：10.1021/es990436i

  日期：1999.10.1

  TNT transformation processes in sediment-free, "natural", aquatic phytoremediation systems of Myriophyllum aquaticum were investigated with specific interest in oxidation products. Extraction procedures combining liquid-liquid extractions and solid-phase extractions were developed for the isolation of the mostly acidic, oxidized TNT metabolites. Six compounds unique from the reduction products of TNT were isolated and characterized by UV-vis, H-1, and C-13 NMR spectroscopy, by mass spectroscopy, and by chemical synthesis where feasible. These compounds include 2-amino-4,6-dinitrobenzoic acid, 2,4-dinitro-6-hydroxy-benzyl alcohol, 2-N-acetoxyamino-4,6-dinitrobenzaldehyde, 2,4-dinitro-6-hydroxytoluene, and two binuclear metabolites unique from the customary azoxytetranitro-toluenes. The monoaryl compounds show clear evidence of oxidative transformations, methyl oxidation and/or aromatic hydroxylation. It is possible that oxidative transformation(s) preceded nitro reduction since studies on exposure of M. aquaticum to either 2-amino-4,6-dinitrotoluene or 4-amino-2,6-dinitrotoluene did not yield any of the oxidation products identified here. The accumulation of oxidation products was significant: 2-amino-4,6-dinitrobenzoic acid, 4.4%; 2,4-dinitro-6-hydroxy-benzyl alcohol, 8.1%; 2-N-acetoxyamino-4,6-dinitrobenzaldehyde, 7.8%; and, 2,4-dinitro-6-hydroxytoluene, 15.6%. The binuclear metabolites accounted for an estimated 5.6%. This study is the first direct evidence for oxidative transformations in aquatic phytoremediation systems.