N-methyl-2-nitro-N-nitrosoaniline | 89937-90-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-methyl-2-nitro-N-nitrosoaniline
• 英文别名: N-nitroso N-methyl-N-(2-nitroaniline)；N-Methyl-2-nitro-N-nitroso-anilin；Methyl-(2-nitro-phenyl)-nitrosamin；N-methyl-N-(2-nitrophenyl)nitrous amide
• CAS: 89937-90-6
• 化学式: C₇H₇N₃O₃
• 分子量: 181.151
• InChiKey: RYQGCRRFWIHSSX-UHFFFAOYSA-N

物化性质

• 沸点：
  345.9±34.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 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：
  78.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-methyl-2-nitro-N-nitrosoaniline 在 ammonium sulfide 作用下， 生成 2-(N-methyl-hydrazino)-aniline
  参考文献：
  名称：

  Hempel, Journal fur praktische Chemie (Leipzig 1954), 1890, vol. <2>41, p. 164

  摘要：

  DOI：
• 作为产物：
  描述：

  N-甲基-2-硝基苯胺 在 盐酸 、 1-(4-(nitrosooxy)butyl)-3-methylimidazolium chloride 作用下， 以 水 为溶剂， 反应 1.5h， 以89%的产率得到N-methyl-2-nitro-N-nitrosoaniline
  参考文献：
  名称：

  离子液体1-（4-硝化丁基）-3-甲基咪唑鎓盐作为在温和条件下对仲胺进行有效N-亚硝化的新试剂

  摘要：

  摘要1-（4-硝基丁基）-3-甲基咪唑鎓盐已开发为一种新型试剂，可在0°C到室温下对仲胺进行高效亚硝化。通过在温和和非均质条件下使用此任务特定的离子液体，可以以极高的收率制备各种N-亚硝胺。 图形概要

  DOI：

  10.1007/s00706-011-0574-7

文献信息

• Effect of Oxygen on the Reaction of Secondary Amines with Nitric Oxide.
  作者：Takashi ITOH、Yuji MATSUYA、Hiromi MAETA、Michiko MIYAZAKI、Kazuhiro NAGATA、Akio OHSAWA

  DOI：10.1248/cpb.47.133

  日期：——

  Secondary amines were allowed to react with nitric oxide in the presence of oxygen to afford N-nitrosamines in good yields. Detailed investigation revealed that the reaction proceeded by two pathways; the one involves the catalytic behavior of oxygen, and the other consumes a stoichiometrical amount of oxygen. Both pathways afforded the same nitroso adducts.

  二级胺可在氧存在下与一氧化氮反应，以良好的产率获得N-亚硝基胺。详细研究表明，该反应经过两条路径进行；其中一条涉及氧的催化行为，另一条则消耗了定量的氧。两条路径均生成了相同的硝基加合物。
• Reaction of Secondary and Tertiary Amines with Nitric Oxide in the Presence of Oxygen.
  作者：Takashi ITOH、Yuji MATSUYA、Hiromi MAETA、Michiko MIYAZAKI、Kazuhiro NAGATA、Akio OHSAWA

  DOI：10.1248/cpb.47.819

  日期：——

  In order to clarify the role of oxygen in the reaction of amines with nitric oxide, secondary amines were allowed to react with nitric oxide in the presence of oxygen. Although N-nitrosamines were obtained as the main products in every case, the yields depended on the substituents and reaction solvents. Detailed investigation revealed that the rection proceeded by at least two pathways : one involving oxygen as a catalyst, and the other consuming the stoichiometric amount of oxygen. Both paths afforded the same nitroso adducts. It was suggested that a third path, a catalytic process via Drago's salts was also possible. The same reaction was applied to a tertiary amine, and it was found that the oxygen was consumed stoichiometrically in this case.

  为了阐明氧在胺与一氧化氮反应中的作用，使二元胺在有氧条件下与一氧化氮反应。虽然每种情况都主要得到N-亚硝基胺产物，但其产率取决于取代基和反应溶剂。详细研究表明，这一反应至少通过两种途径进行：一种涉及氧气作为催化剂，另一种则消耗当量氧。两条途径都生成相同的亚硝基加合物。有人提出，还可能存在第三条途径，即通过德拉戈盐的催化过程。将同样的反应应用于三元胺，结果发现，这次氧气是按化学计量被消耗的。
• Observation of a single-pot aromatic reductive denitration
  作者：Angelo G. Giumanini、Giancarlo Verardo

  DOI：10.1139/v97-054

  日期：1997.4.1

  4,N,N-Trimethyl-3-nitrobenzenamine gave reductive denitration products (ca. 28%) upon treatment with n-butyl nitrite in the presence of catalytic amounts of ammonium chloride and water in an unprecedented one-reagent single-pot process. The three isomeric N,N-dimethylnitrobenzenamines showed the same behaviour to a much lesser extent; the ortho isomer was partially (7%) transformed into 1-methylbenzotriazole. Keywords: aromatic protolytic denitration, nitroaromatics, n-butyl nitrite, E- and Z-nitrosamine.

  4，N，N-三甲基-3-硝基苯胺在氯化铵和水存在下，与正丁硝酸酯处理后产生还原脱硝产物（约28%）在一个前所未有的单试剂单锅过程中。三种同分异构的N，N-二甲基硝基苯胺以较小程度显示相同行为；邻位异构体部分（7%）转化为1-甲基苯并三唑。关键词：芳香质子化脱硝，硝基芳烃，正丁硝酸酯，E-和Z-亚硝胺。
• Rhodium(<scp>iii</scp>)-catalyzed indole synthesis at room temperature using the transient oxidizing directing group strategy
  作者：Yaping Shang、Krishna Jonnada、Subhash Laxman Yedage、Hua Tu、Xiaofeng Zhang、Xin Lou、Shijun Huang、Weiping Su

  DOI：10.1039/c9cc04529e

  日期：——

  temperature have been developed using an in situ generated N-nitroso group as a transient oxidizing directing group. Due to mild reaction conditions, this method enabled synthesis of a broad range of N-alkyl indoles, including even two indole-based medicinal compounds. Our work disclosed the feasibility of the transient oxidizing directing group strategy in C–H functionalization reactions, which possesses

  在室温下，N-烷基苯胺与内部炔烃的Rh催化反应已经使用原位生成的N-亚硝基作为过渡性氧化导向基团进行了开发。由于反应条件温和，该方法能够合成多种N-烷基吲哚，甚至包括两种基于吲哚的药用化合物。我们的工作揭示了在C–H功能化反应中采用瞬态氧化指导基团策略的可行性，该策略具有增强整体步骤经济性和赋予底物新的反应性模式的潜力。
• Regioselective nitration of anilines with Fe(NO₃)₃·9H₂O as a promoter and a nitro source
  作者：Yang Gao、Yuanyou Mao、Biwei Zhang、Yingying Zhan、Yanping Huo

  DOI：10.1039/c8ob00841h

  日期：——

  An efficient Fe(NO3)3·9H2O promoted ortho-nitration reaction of aniline derivatives has been developed. This reaction may go through a nitrogen dioxide radical (NO2˙) intermediate, which is generated by the thermal decomposition of iron(III) nitrate. The practicality of the present method using nontoxic and inexpensive iron reagents has been shown by the broad substrate scope and applications.

  已经开发出一种有效的Fe（NO 3）3 ·9H 2 O促进苯胺衍生物的邻位硝化反应。该反应可能通过二氧化氮自由基（NO 2）中间体，该中间体是由硝酸铁（III）的热分解产生的。广泛的底物范围和应用已经证明了使用无毒且廉价的铁试剂的本方法的实用性。