N,N-dimethyl-4-(2-chloro-4-nitrophenylazo)aniline | 3150-84-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: N,N-dimethyl-4-(2-chloro-4-nitrophenylazo)aniline
• 英文别名: 4-[(E)-(2-Chloro-4-nitrophenyl)diazenyl]-N,N-dimethylaniline；4-[(2-chloro-4-nitrophenyl)diazenyl]-N,N-dimethylaniline
• CAS: 3150-84-3
• 化学式: C₁₄H₁₃ClN₄O₂
• 分子量: 304.736
• InChiKey: GUMVUIYWNPHCHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2927000090

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-4-(2-chloro-4-nitrophenylazo)aniline 在 乙醇 、 水 、 sodium sulfite 作用下， 反应 1.0h， 生成 4-[(4-氨基-2-氯苯基)偶氮]-N,N-二甲基苯胺
  参考文献：
  名称：

  WO2008/34650

  摘要：

  公开号：
• 作为产物：
  描述：

  N,N-二甲基苯胺 在 盐酸 、 sodium nitrite 、 potassium carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 3.0h， 生成 N,N-dimethyl-4-(2-chloro-4-nitrophenylazo)aniline
  参考文献：
  名称：

  WO2008/34650

  摘要：

  公开号：

文献信息

• Synthesis of a nitrite functionalized star-like poly ionic compound as a highly efficient nitrosonium source and catalyst for the diazotization of anilines and subsequent facile synthesis of azo dyes under solvent-free conditions
  作者：Hassan Valizadeh、Ashkan Shomali、Jalal Ghorbani、Saeideh Noorshargh

  DOI：10.1016/j.dyepig.2015.02.007

  日期：2015.6

  star-like poly ionic (NFSPI) compound was synthesized and used as a highly efficient nitrosonium source and catalyst for the conversion of aniline derivatives to diazonium salts. Azo dyes were prepared via in situ azo-coupling reaction of these diazoniums with active aromatic compounds under solvent-free conditions in very short reaction time in excellent yields. NFSPI plays dual role as a three-dimensional

  合成了亚硝酸盐官能化的星形聚离子（NFSPI）化合物，并将其用作高效的硝态氮源和催化剂，用于将苯胺衍生物转化为重氮盐。偶氮染料是通过在没有溶剂的条件下，这些重氮鎓与活性芳香族化合物在非常短的反应时间内以极高的收率进行原位偶氮偶合反应而制备的。NFSPI由于具有多离子特性，因此可作为三维硝态氮源和催化剂发挥双重作用。分离出的产物经FT-IR光谱，1 H-NMR，13确证。C-NMR光谱和CHNSO分析。通过FT-IR光谱，SEM图像，EDX和CHNSO分析确认了非均相试剂和催化剂的结构。通过该程序合成各种产物的产率和反应时间与文献报道的值进行了比较。
• The Thermal Isomerization of Azobenzenes. III. Substituent, Solvent, and Pressure Effects on the Thermal Isomerization of Push-pull Azobenzenes
  作者：Norio Nishimura、Shinya Kosako、Yoshimi Sueishi

  DOI：10.1246/bcsj.57.1617

  日期：1984.6

  4-(dimethylamino)azobenzene (DAAB) derivatives, and no fundamental difference in the kinetic-substituent effects was observed between NDAAB and DAAB. The volume of activation, which is of a negative value, varies remarkably from solvent to solvent and from substituent to substituent; its magnitude increases generally with an increase in the solvent polarity. Even for DAAB and 4,4′-bis(diethylamino)azobenzene (BDEAAB)

  研究了取代基、溶剂和压力对 4-二甲氨基-4'-硝基偶氮苯 (NDAAB) 衍生物的热顺反异构化速率的影响。2-甲基-和 2'-氯-NDAAB 异构化速度比 NDAAB 快，2'-甲基-和 2-氯-NDAAB 异构化速度比 NDAAB 慢。对于 2,2'-二甲基-和 2,2'-二氯-NDAAB，速率介于单取代的速率之间。这些发现与 4-（二甲氨基）偶氮苯 (DAAB) 衍生物的发现非常相似，在 NDAAB 和 DAAB 之间没有观察到动力学取代基效应的根本差异。活化体积为负值，随溶剂和取代基的不同而显着变化；它的大小通常随着溶剂极性的增加而增加。即使对于 DAAB 和 4，4'-双（二乙氨基）偶氮苯 (BDEAAB)，极性溶剂中的外部压力可明显加快该速率。得出的结论是，观察到的结果与逆...
• New Generation of Nitrite Functionalized Star-like Polyvinyl Imidazolium Compound: Application as a Nitrosonium Source and Three Dimensional Nanocatalyst for the Synthesis of Azo Dyes
  作者：Ashkan Shomali、Hassan Valizadeh、Saeideh Noorshargh

  DOI：10.2174/1570178614666170321125216

  日期：2017.6.14

  Background: The compounds with three-dimensional and ionic structures have attracted considerable attentions because of their unique characteristics as a drug carrier and catalyst. Star-like poly ionic compounds are a new generation of three-dimensional structures which have both; the exclusive ionic features and three-dimensional structures. Recently, we reported the synthesis of diazonium salts from aniline derivatives using carboxyl and nitrite functionalized graphene quantum dots. Methods: Nitrite-functionalized star-like polyionic (NFSP) compound was synthesized as a new generation of three-dimensional nanocatalyst. Herein, the use of NFSP as an efficient reagent and nanocatalyst for the diazotization of aniline derivatives and subsequent synthesis of azo dyes via the reaction with active phenolates under solvent-free conditions was reported. Results: In order to demonstrate the positive impact of NFSP efficiency, the reaction times and yields of the products were compared with other methods and catalysts which have been reported previously. The brilliant performance of NFSP can be ascribed to multifunctional reagent and also trapping the ingredient within catalyst cavities. Conclusion: A highly effective and cost-effective method has been developed for the preparation of azo dyes. In reported method, new three-dimensional catalyst with highly ionic characteristic and multifunctional nitrosonium source is available. These special features reduced the required amount of catalyst, reaction time and also increased the efficiency of catalyst.

  背景：具有三维和离子结构的化合物因其作为药物载体和催化剂的独特特性而备受关注。星状多离子化合物是新一代的三维结构化合物，同时具有独特的离子特性和三维结构。最近，我们报道了利用羧基和亚硝基功能化石墨烯量子点从苯胺衍生物中合成重氮盐的方法：合成了亚硝酸盐功能化星状多离子（NFSP）化合物，作为新一代三维纳米催化剂。结果：为了证明 NFSP 效率的积极影响，将反应时间和产物产率与之前报道过的其他方法和催化剂进行了比较。 NFSP 的出色性能可归因于多功能试剂以及催化剂空腔内成分的捕获。 结论：已开发出一种高效、经济的偶氮染料制备方法。在报告的方法中，新型三维催化剂具有高离子特性和多功能硝基锍源。这些特点不仅减少了催化剂的用量，缩短了反应时间，还提高了催化剂的效率。
• WO2008/34650
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  公开号：——

  公开（公告）日：——