苄基-(3-硝基-苯基)-胺 | 33334-94-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 苄基-(3-硝基-苯基)-胺
• 英文名称: N-benzyl-m-nitroaniline
• 英文别名: N-benzyl-3-nitroaniline；N-(3-nitrophenyl)benzylamine；N-Benzyl-m-nitroanilin
• CAS: 33334-94-0
• 化学式: C₁₃H₁₂N₂O₂
• mdl: MFCD00097793
• 分子量: 228.25
• InChiKey: OVZNWAWUJPSLHM-UHFFFAOYSA-N

物化性质

• 熔点：
  106 °C
• 沸点：
  223-224 °C(Press: 3 Torr)
• 密度：
  1.258±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2921420090

反应信息

• 作为反应物：
  描述：

  苄基-(3-硝基-苯基)-胺 在 ammonium formate 作用下， 以 乙二醇 为溶剂， 反应 9.0h， 以77%的产率得到N¹-benzylbenzene-1,3-diamine
  参考文献：
  名称：

  铜纳米颗粒/甲酸铵可高度化学选择性还原芳香族硝基化合物。

  摘要：

  通过将铜纳米颗粒和甲酸铵在乙二醇中的组合在120摄氏度下实现了芳香族硝基化合物向相应氨基衍生物的高度化学选择性还原。在多种其他可还原官能团的存在下成功进行了还原在分子中，例如Cl，I，OCH2Ph，NHCH2Ph，COR，COOR，CN等。反应非常干净，收率很高。

  DOI：

  10.1021/jo800863m
• 作为产物：
  描述：

  N-苄基-N-(3-硝基苯基)甲酰胺 生成 苄基-(3-硝基-苯基)-胺
  参考文献：
  名称：

  Mori,K. et al., Chemical and pharmaceutical bulletin, 1971, vol. 19, p. 1722 - 1727

  摘要：

  DOI：

文献信息

• Room-Temperature Copper-Catalyzed Carbon-Nitrogen Coupling of Aryl Iodides and Bromides Promoted by Organic Ionic Bases
  作者：Chu-Ting Yang、Yao Fu、Yao-Bing Huang、Jun Yi、Qing-Xiang Guo、Lei Liu

  DOI：10.1002/anie.200903158

  日期：2009.9.21

  solubility alone does not explain the performance of organic ionic bases in the room‐temperature coupling of aryl iodides and even bromides with aliphatic and aromatic amines and N‐heterocycles (NuH; see scheme). Conductivity measurements show that these organic ionic bases, which contain tetraalkylammonium or ‐phosphonium cations, are readily ionized in organic solvents.

  仅仅良好的溶解度并不能解释有机离子碱在芳基碘化物甚至溴化物与脂族和芳族胺以及N杂环的室温偶联中的性能（NuH；参见方案）。电导率测量表明，这些含有四烷基铵或阳离子的有机离子碱在有机溶剂中很容易被电离。
• Copper-catalyzed formation of carbon-heteroatom and carbon-carbon bonds
  申请人：——

  公开号：US20030065187A1

  公开（公告）日：2003-04-03

  The present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide or amine moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In additional embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between a nitrogen atom of an acyl hydrazine and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of a nitrogen-containing heteroaromatic, e.g., indole, pyrazole, and indazole, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-oxygen bond between the oxygen atom of an alcohol and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. The present invention also relates to copper-catalyzed methods of forming a carbon-carbon bond between a reactant comprising a nucleophilic carbon atom, e.g., an enolate or malonate anion, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. Importantly, all the methods of the present invention are relatively inexpensive to practice due to the low cost of the copper comprised by the catalysts.

  本发明涉及铜催化的碳-杂原子和碳-碳键形成方法。在某些实施例中，本发明涉及铜催化的方法，用于在酰胺或胺基团的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在其他实施例中，本发明涉及铜催化的方法，用于在酰基肼的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在另一些实施例中，本发明涉及铜催化的方法，用于在含氮杂环芳烃（例如吲哚、吡唑和吲哌）的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在某些实施例中，本发明涉及铜催化的方法，用于在醇的氧原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氧键。本发明还涉及铜催化的方法，用于在包含亲核碳原子的反应物（例如烯醇酸盐或丙二酸盐负离子）与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-碳键。重要的是，由于催化剂中铜的低成本，本发明的所有方法都相对廉价。
• FeS-NH₄CL-CH₃OH-H₂O: AN EFFICIENT AND INEXPENSIVE SYSTEM FOR REDUCTION OF NITROARENES TO ANILINES^*
  作者：D. G. Desai、S. S. Swami、S. K. Dabhade、M. G. Ghagare

  DOI：10.1081/scc-100104012

  日期：2001.1.1

  Nitroarenes are reduced to corresponding anilines with FeS-NH4Cl-CH3OH-H2O system in good yields. *Work carried out at R. B. N. B. College, Shrirampur – 413 709, India.

  用 FeS-NH4Cl-CH3OH-H2O 系统以良好的收率将硝基芳烃还原为相应的苯胺。*工作在 RBNB College, Shrirampur – 413 709, India 进行。
• Metal-Free Reduction of Aromatic and Aliphatic Nitro Compounds to Amines: A HSiCl₃-Mediated Reaction of Wide General Applicability
  作者：M. Orlandi、F. Tosi、M. Bonsignore、M. Benaglia

  DOI：10.1021/acs.orglett.5b01698

  日期：2015.8.21

  A new, mild, metal-free, HSiCl3-mediated reduction of both aromatic and aliphatic nitro groups to amines that is of wide general applicability, tolerant of many functional groups, and respectful of the stereochemical integrity of stereocenters is reported.

  报道了一种新的，温和的，不含金属的，HSiCl 3介导的将芳族和脂肪族硝基均还原为胺的方法，该方法具有广泛的通用性，可耐受许多官能团，并尊重立体中心的立体化学完整性。
• N-Alkylation of amines with alcohols over nanosized zeolite beta
  作者：Marri Mahender Reddy、Macharla Arun Kumar、Peraka Swamy、Mameda Naresh、Kodumuri Srujana、Lanka Satyanarayana、Akula Venugopal、Nama Narender

  DOI：10.1039/c3gc41345d

  日期：——

  Direct N-alkylation of amines with alcohols was successfully performed by using nanosized zeolite beta, which showed the highest catalytic activity among other conventional zeolites. This method has several advantages, such as eco-friendliness, moderate to high yields, and simple work-up procedure. The catalyst was successfully recovered and reused without significant loss of activity and only water is produced as co-product. In addition, imines were also efficiently prepared from the tandem reactions of amines with 2-, 3- and 4-nitrobenzyl alcohols using nanosized zeolite beta.

  使用纳米尺寸的Beta沸石成功实现了胺与醇的直接N-烷基化反应，Beta沸石在其他传统沸石中显示出最高的催化活性。该方法具有多个优点，如环保性、适中至高产率以及简便的后续处理程序。催化剂可成功回收并重复使用，活性无明显损失，副产物仅为水。此外，通过使用纳米尺寸的Beta沸石，胺与2-、3-和4-硝基苄醇的串联反应也能高效制备亚胺。