2-amino-4-hydroxylamino-5-hydroxyl-6-nitrotoluene | 220493-56-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-amino-4-hydroxylamino-5-hydroxyl-6-nitrotoluene
• 英文别名: 4-amino-6-hydroxylamino-3-methyl-2-nitrophenol；4-amino-6-(hydroxyamino)-3-methyl-2-nitrophenol
• CAS: 220493-56-1
• 化学式: C₇H₉N₃O₄
• 分子量: 199.166
• InChiKey: FKJGBYBJSUZHRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 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：
  124
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-羟基氨基-4,6-二硝基甲苯 在 biological components of crude cell extract Clostridium acetobutylicum 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 48.0h， 生成 2-amino-4-hydroxylamino-5-hydroxyl-6-nitrotoluene
  参考文献：
  名称：

  Bamberger Rearrangement during TNT Metabolism by Clostridium acetobutylicum

  摘要：

  Studies were conducted to isolate and identify polar and oxygen-sensitive intermediates of 2,4,6-trinitrotoluene (TNT) transformation by Clostridium acetobutylicum. Studies conducted in anaerobic cell extracts demonstrated that a polar product formed from the transformation of 2,4-dihydroxylamino-6-nitrotoluene by a mechanism known as the Bamberger rearrangement. The product was stabilized by derivatization with acetic anhydride, and the structure was confirmed by mass spectroscopy, (1)H NMR, and IR spectroscopy techniques. The reaction occurred in the presence of cell extract and H(2) but did not occur in cell extract-free controls. From spectroscopic data, the product of 2,4-dihydroxylamino-6-nitrotoluene rearrangement was identified as either 2-amino-4-hydroxylamino-5-hydroxyl-6-nitrotoluene (4-amino-6-hydroxylamino-3-methyl-2-nitrophenol) or 2-hydroxylamino-4-amino-5-hydroxyl-6-nitrotoluene (6-amino-4-hydroxylamino-3-methyl-2-nitrophenol). Acid-catalyzed rearrangement of 2,4-dihydroxylamino-6-nitrotoluene resulted in a single product, which after derivatization, was identical to a derivatized product from cell extracts. Acid-catalyzed Bamberger rearrangement occurs with the hydroxyl addition para to the participating hydroxylamine, indicating that the 2-amino-4-hydroxylamino-5-hydroxyl-6-nitrotoluene (4-amino-6-hydroxylamino-3-methyl-2-nitrophenol) was the product isolated form cell extracts. This product was also confirmed in whole cell systems that had been fed TNT. Following derivatization of the culture broth, a product was isolated that was identical to hose isolated from crude cell extracts and acid catalysis experiments.

  DOI：

  10.1021/es970612s

文献信息

• NITRO-BASED EXPLOSIVE REMEDIATION
  申请人：Craig A. Morrie

  公开号：US20110052537A1

  公开（公告）日：2011-03-03

  Embodiments of techniques for remediating soil contaminated with compounds, particularly nitro-based explosives, are disclosed. Plants capable of taking up the compounds are grown within contaminated soil for a period of time. The plants are exposed to anaerobic microbes in the rumen of a ruminant animal. The ruminal anaerobic microbes degrade the remediable compounds and render them substantially nontoxic to the animal. In some embodiments, the remediable compounds are nitroaromatic compounds, and are degraded by nitroreductases. In other embodiments, microbes are transferred from a consortium enriched in microbes capable of degrading the remediable compounds to a ruminant animal that lacks microbes capable of degrading the remediable compounds. In other embodiments, methods for isolating and identifying ruminal anaerobic microbes capable of degrading remediable compounds are disclosed.

  本发明揭示了一种用于修复含有化合物的土壤，特别是含有硝基炸药的技术实施方案。在受污染的土壤中种植能够吸收这些化合物的植物，一段时间后，将这些植物暴露在反刍动物瘤胃内的厌氧微生物中。瘤胃内的厌氧微生物降解可修复的化合物，并使其在动物体内基本无毒。在某些实施方案中，可修复的化合物是硝基芳香化合物，并通过硝基还原酶降解。在其他实施方案中，从富含能够降解可修复化合物的微生物群落中转移微生物到缺乏能力降解可修复化合物的反刍动物体内。在其他实施方案中，揭示了用于分离和鉴定能够降解可修复化合物的瘤胃内厌氧微生物的方法。
• Bamberger Rearrangement during TNT Metabolism by <i>Clostridium acetobutylicum</i>
  作者：J. B. Hughes、C. Wang、K. Yesland、A. Richardson、R. Bhadra、G. Bennett、F. Rudolph

  DOI：10.1021/es970612s

  日期：1998.2.1

  Studies were conducted to isolate and identify polar and oxygen-sensitive intermediates of 2,4,6-trinitrotoluene (TNT) transformation by Clostridium acetobutylicum. Studies conducted in anaerobic cell extracts demonstrated that a polar product formed from the transformation of 2,4-dihydroxylamino-6-nitrotoluene by a mechanism known as the Bamberger rearrangement. The product was stabilized by derivatization with acetic anhydride, and the structure was confirmed by mass spectroscopy, (1)H NMR, and IR spectroscopy techniques. The reaction occurred in the presence of cell extract and H(2) but did not occur in cell extract-free controls. From spectroscopic data, the product of 2,4-dihydroxylamino-6-nitrotoluene rearrangement was identified as either 2-amino-4-hydroxylamino-5-hydroxyl-6-nitrotoluene (4-amino-6-hydroxylamino-3-methyl-2-nitrophenol) or 2-hydroxylamino-4-amino-5-hydroxyl-6-nitrotoluene (6-amino-4-hydroxylamino-3-methyl-2-nitrophenol). Acid-catalyzed rearrangement of 2,4-dihydroxylamino-6-nitrotoluene resulted in a single product, which after derivatization, was identical to a derivatized product from cell extracts. Acid-catalyzed Bamberger rearrangement occurs with the hydroxyl addition para to the participating hydroxylamine, indicating that the 2-amino-4-hydroxylamino-5-hydroxyl-6-nitrotoluene (4-amino-6-hydroxylamino-3-methyl-2-nitrophenol) was the product isolated form cell extracts. This product was also confirmed in whole cell systems that had been fed TNT. Following derivatization of the culture broth, a product was isolated that was identical to hose isolated from crude cell extracts and acid catalysis experiments.