1-N-2,4-二硝基苯基二甲胺 | 1670-17-3

• 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: 1-N-2,4-二硝基苯基二甲胺
• 英文名称: N,N-dimethyl-2,4-dinitroaniline
• 英文别名: N,N-Dimethyl-2,4-dinitro-anilin；2,4-dinitro-N,N-dimethylaniline；2,4-Dinitro-N,N-dimethylanilin；2,4-Dinitro-dimethyl-anilin；N,N-dimethyl-2,4-dinitrobenzenamine
• CAS: 1670-17-3
• 化学式: C₈H₉N₃O₄
• mdl: MFCD00452305
• 分子量: 211.177
• InChiKey: HJFZYZBHIAWDEO-UHFFFAOYSA-N

物化性质

• 熔点：
  178 °C
• 沸点：
  350.85°C (rough estimate)
• 密度：
  1.4271 (rough estimate)
• 溶解度：
  氯仿（微溶）、甲醇（微溶、加热）

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  94.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-N-2,4-二硝基苯基二甲胺 在 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 生成 2,4-二硝基酚
  参考文献：
  名称：

  15 N NMR and FTIR studies of 2,4-dinitroanilines and their salts

  摘要：

  Twenty-two 2,4-dinitroanilines were synthesised and their pK(a) values were determined. The 2,4-dinitroanilines and their protonated forms were studied by N-15 NMR spectroscopy. The relations between the N-15 NMR chemical shifts and the pK(a) values of the 2,4-dinitroanilines and their salts were found to be linear. The deprotonation reaction of N-methyl-2,4-dinitroanilines and N-methyl-2,4,6-trinitroaniline by MTBD was successful only for the latter and yielded protonated MTBD molecule and the anion in which the electrons are strongly delocalised. The kinetic parameters of the 2,4-dinitroanilines in reactions with hydroxide ions in mixed solvent DMSO:water (95:5, v/v) were determinated and discussed. (C) 2000 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-2860(00)00379-3
• 作为产物：
  描述：

  N,N-二甲基苯胺 在 bismuth (III) nitrate pentahydrate 、 palladium diacetate 作用下， 以 2,2,2-三氟乙醇 、 三氟乙酸 为溶剂， 反应 24.0h， 以86%的产率得到1-N-2,4-二硝基苯基二甲胺
  参考文献：
  名称：

  Pd（OAc）2催化芳香胺的硝化反应

  摘要：

  利用Pd（OAc）2与Bi（NO 3）3 ·5H 2 O在三氟乙醇（TFE）和三氟乙酸（TFA）中催化的硝化反应，我们开发了一种高效且实用的方法来合成仲二硝基-芳香胺。该产品可用于制备5-胺-N-甲基-苯并咪唑酮，具有偶氮染料的经济优势。该方法还扩展到某些叔芳族胺的硝化反应。

  DOI：

  10.1016/j.tet.2015.04.013

文献信息

• Photoredox Catalyzed Dealkylative Aromatic Halogen Substitution with Tertiary Amines
  作者：Dmitry L. Lipilin、Alexander E. Frumkin、Alexey Y. Tyurin、Vitalij V. Levin、Alexander D. Dilman

  DOI：10.3390/molecules26113323

  日期：——

  A reaction of aromatic halides bearing electron-withdrawing groups with tertiary amines in the presence of an iridium catalyst under blue light irradiation is described. Products of the aromatic substitution of the halide by the dialkylamino fragment are obtained. The interaction of aryl radicals with tertiary amines to generate zwitterionic radical species is believed to be the key factor responsible

  描述了带有吸电子基团的芳香族卤化物与叔胺在铱催化剂存在下在蓝光照射下的反应。获得卤化物被二烷基氨基片段芳族取代的产物。芳基自由基与叔胺相互作用产生两性离子自由基物种被认为是影响反应效率的关键因素。
• Aromatic nucleophilic substitution reactions of 1-dialkylamino-substituted activated benzenes with various amines in dimethyl sulfoxide
  作者：Shizen Sekiguchi、Hiromi Ishikura、Yukitoshi Hirosawa、Nobuyuki Ono

  DOI：10.1016/s0040-4020(01)87755-3

  日期：1990.1

  In the reactions of 1-d1a1kylamino-2,4,6-trinitro- and 1-dialkylam1no-2, 4-dinitrobenzenes with various amines in dimethyl sulfoxide, 1-dialkylamino group is easily replaced with primary n-alkylamines at room temperature, and in a low yield with pyrrolidine only among secondary amines.

  在二甲基亚砜中1-d1a1kylamino-2,4,6-三硝基和1-dialkam1no-2、4-二硝基苯与各种胺的反应中，1-二烷基氨基很容易在室温下被伯正烷基胺取代，并且仅仲胺中吡咯烷的收率低。
• First Application of Heterogeneous Cobalt Catalysis in C_sp2-N Cross-Coupling of Activated Chloroarenes under Ligand-Free Conditions
  作者：Nirmalya Mukherjee、Tanmay Chatterjee、Brindaban C. Ranu

  DOI：10.1002/ejoc.201500418

  日期：2015.6

  A heterogeneous CoII/Al2O3 catalyst efficiently catalyses the N-arylation of N-heterocycles and open-chain secondary amines by activated chloroarenes and chloroheteroarenes under ligand-free conditions in water to give a series of functionalized tertiary amines. The catalyst was prepared by immobilizing CoBr2 onto the surface of Al2O3, and was characterized by X-ray diffraction, X-ray photoelectron

  多相 CoII/Al2O3 催化剂在水中无配体条件下，通过活化的氯芳烃和氯杂芳烃有效催化 N-杂环和开链仲胺的 N-芳基化，得到一系列官能化叔胺。该催化剂通过将 CoBr2 固定在 Al2O3 表面上制备，并通过 X 射线衍射、X 射线光电子能谱、扫描电子显微镜和能量色散 X 射线分析进行表征。这种催化剂最多可以循环使用六次，而催化活性没有任何明显的损失。
• Reaction Products of Activated Aromatic and Heteroaromatic Chlorides with <i>N,N</i>-Disubstituted Formamides
  作者：Zdzisław Brzozowski、Jarosław Sławiński

  DOI：10.1080/00397910903136118

  日期：2010.5.11

  N-disubstituted aromatic amines (3a–g) was obtained in very good yield by the reaction of adequate doubly activated aromatic or heteroaromatic halides (1a–e) with N,N-disubstituted formamides (2a–c). Analogously, starting from 4-chloro-3-pyridinesulfonamide, the appropriate 4-dialkylamino-1H +-pyridinium-3-(N-formyl)sulfonamidates (5a,b) were obtained in 52–60% yield. Mechanisms of the reactions are discussed

  通过足够的双活化芳香族或杂芳香族卤化物（1a-e）与 N,N-二取代甲酰胺（2a-c）反应，以非常好的收率获得了几种 N,N-二取代芳香胺（3a-g）。类似地，从 4-氯-3-吡啶磺酰胺开始，以 52-60% 的产率获得了合适的 4-二烷基氨基-1H +-吡啶鎓-3-(N-甲酰基)磺酰胺 (5a,b)。讨论了反应机理。
• General method for nucleophilic aromatic substitution of aryl fluorides and chlorides with dimethylamine using hydroxide-assisted decomposition of N,N-dimethylforamide
  作者：Juana Garcia、Jacob Sorrentino、Emily J. Diller、Daniel Chapman、Zachary R. Woydziak

  DOI：10.1080/00397911.2016.1147051

  日期：2016.3.3

  and convenient procedure for the nucleophilic aromatic substitution of aryl fluorides and chlorides with dimethylamine was developed using a hydroxide-assisted thermal decomposition of N,N-dimethylforamide. These conditions are tolerant of nitro, nitrile, aldehyde, ketone, and amide groups but will undergo acyl substitution to form amides for methyl esters and acyl chlorides. Isolated yields of the products

  摘要 利用 N,N-二甲基甲酰胺的氢氧化物辅助热分解，开发了一种实用且方便的方法，用于芳基氟化物和氯化物与二甲胺的亲核芳香取代。这些条件耐受硝基、腈、醛、酮和酰胺基团，但会发生酰基取代以形成甲酯和酰氯的酰胺。产品的分离产率范围为 44% 至 98%，其中 17 个实例的大多数产率大于 70%。图形概要