2-Phenyl-azo-N-methylanilin | 74936-84-8

• 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: 2-Phenyl-azo-N-methylanilin
• 英文别名: Methylaminoazobenzene；N-methyl-2-phenyldiazenylaniline
• CAS: 74936-84-8
• 化学式: C₁₃H₁₃N₃
• 分子量: 211.266
• InChiKey: CPKKERYUBQHXOC-UHFFFAOYSA-N

物化性质

• 沸点：
  369.3±25.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  36.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  sodium tetrachloropalladate(II) 、 2-Phenyl-azo-N-methylanilin 以 甲醇 为溶剂， 以55%的产率得到
  参考文献：
  名称：

  A strategy of Pd(II) assisted C–H activation in 2-alkylamino azobenzene ligands: Syntheses, characterisation and structure of a new family of orthopalladated complexes

  摘要：

  Several 2-(arylazo)-N-alkyl aniline ligands, 1a-11a, have been prepared by the reaction between 2-(arylazo) aniline and the appropriate alkyl halide in the presence of K2CO3. Treatment of sodium tetrachloropallaclate with 1a-11a in methanol afforded the orthopalladated complexes 1b-11b, where the ligand is tridentate (C,N,N). The ligands and complexes were characterised from spectroscopic data and confirmed by X-ray studies. The X-ray Structure of 9b displayed an unsupported Pd(II)Pd-...(II) interaction (3.301 angstrom). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2005.05.022
• 作为产物：
  描述：

  2-苯基偶氮苯甲酰苯胺 在 盐酸 、 氢氧化钾 、 sodium hydroxide 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 107.0h， 生成 2-Phenyl-azo-N-methylanilin
  参考文献：
  名称：

  Syntheses and Properties of 1-Methyl-3-phenylaminobenzimidazolium Salts, Models of DNA Adducts of N7-Arylaminodeoxyguanosinium Salt

  摘要：

  When arylaminating carcinogens are administered to cells, they mainly generate the C8-arylamino-2'-deoxyguanosine adduct in DNA. A mechanism for this was proposed in which N7-arylaminated 2'-deoxyguanosine acts as an intermediate; however, it remained unclear whether this is actually the case. To elucidate the mechanisms involved in the generation of this adduct, a series of 5-substituted 1-methylbenzimidazole derivatives were used as models of the imidazole moiety of 2'-deoxyguanosine. Syntheses of a series of 5-substituted (CH3, H, F, CF3, or NO2) 1-methyl-3-phenylaminobenzimidazolium salts (7) and their related compounds were carried out, and the chemical characteristics of these products were examined. Keating compound 7 at 80 degreesC for 48 h in H2O/MeOH provided 5-substituted 1-methyl-2-oxo-2,3-dihydrobenzimidazoles but only when this compound contained a CF3 or NO2 substituent. Compound 7 decomposed in alkaline media, and its rate of decomposition increased when this compound had a stronger electron-withdrawing substituent. The product obtained under these conditions was 4-substituted N-1-methyl-2-phenylazoaniline. On the other hand, when 1-methyl-3-(4-nitrophenylamino)benzimidazolium salt was treated under the same conditions as described above, it generated, a demethylated product, 1-(4-nitrophenylamino)benzimidazole, when heated in H2O/MeOH and N-1-formyl-N-1-methyl-2-phenylazoaniline when treated in alkaline media. When the chemical characteristics of 3-phenylamino and 3-amino groups were compared using 3-substituted 1-methyl-5-(trifluoromethyl)benzimidazole the 3-phenylamino derivative was found to be more reactive.

  DOI：

  10.1021/tx0000724

文献信息

• FILLER COMPOSITION INDICATING READINESS TO SAND
  申请人：ILLINOIS TOOL WORKS INC.

  公开号：US20190023931A1

  公开（公告）日：2019-01-24

  A vehicle bond filler formulation is provided that includes a part A having curable resin and a monomer reactive diluent. A part B storage-separate, cure initiator package contains a free-radical cure initiator. At least one color changing dye adapted to change color upon mixing the part A and the part B and within ±5 minutes of cure of the curable resin to a sandable condition is present in either the part A or a separate part C, a guide coat colorant, or a combination thereof. A process of for repairing a vehicle body is also provided that includes mixing a part A containing the at least one color changing dye with the part B to form an internal guide coat mixture applied to a substrate of the vehicle body in need of repair. The mixture cures causing the color changing dye to the terminal change color within ±5 minutes of cure of the curable resin to a sandable condition.
• PRIMER WITH INTERNAL GUIDE COAT
  申请人：Twardowska Helena

  公开号：US20200239710A1

  公开（公告）日：2020-07-30

  A free radical curable automotive body primer is provided that has a color change corresponding to the progress of the cure process until a dry to sand condition has been attained and an internal colored guide coat that does not change color given its exposure to ambient air and as a result, has a different color on the surface of the primer than when in bulk, allowing for the detection and removal of low spots or other imperfections from a vehicle body by additional sanding of the inventive primer to remove oxidized guide coat colorant surface regions. The cure color change is achieved through resort to at least one color changing dye that reacts with a free radical cure initiator during the vehicle body priming process and changes color to indicate when the primer composition has achieved a level of cure so as to be dry enough to sand.
• Syntheses and Properties of 1-Methyl-3-phenylaminobenzimidazolium Salts, Models of DNA Adducts of N7-Arylaminodeoxyguanosinium Salt
  作者：Toyo Kaiya、Tomoko Fujiwara、Kohfuku Kohda

  DOI：10.1021/tx0000724

  日期：2000.10.1

  When arylaminating carcinogens are administered to cells, they mainly generate the C8-arylamino-2'-deoxyguanosine adduct in DNA. A mechanism for this was proposed in which N7-arylaminated 2'-deoxyguanosine acts as an intermediate; however, it remained unclear whether this is actually the case. To elucidate the mechanisms involved in the generation of this adduct, a series of 5-substituted 1-methylbenzimidazole derivatives were used as models of the imidazole moiety of 2'-deoxyguanosine. Syntheses of a series of 5-substituted (CH3, H, F, CF3, or NO2) 1-methyl-3-phenylaminobenzimidazolium salts (7) and their related compounds were carried out, and the chemical characteristics of these products were examined. Keating compound 7 at 80 degreesC for 48 h in H2O/MeOH provided 5-substituted 1-methyl-2-oxo-2,3-dihydrobenzimidazoles but only when this compound contained a CF3 or NO2 substituent. Compound 7 decomposed in alkaline media, and its rate of decomposition increased when this compound had a stronger electron-withdrawing substituent. The product obtained under these conditions was 4-substituted N-1-methyl-2-phenylazoaniline. On the other hand, when 1-methyl-3-(4-nitrophenylamino)benzimidazolium salt was treated under the same conditions as described above, it generated, a demethylated product, 1-(4-nitrophenylamino)benzimidazole, when heated in H2O/MeOH and N-1-formyl-N-1-methyl-2-phenylazoaniline when treated in alkaline media. When the chemical characteristics of 3-phenylamino and 3-amino groups were compared using 3-substituted 1-methyl-5-(trifluoromethyl)benzimidazole the 3-phenylamino derivative was found to be more reactive.
• A strategy of Pd(II) assisted C–H activation in 2-alkylamino azobenzene ligands: Syntheses, characterisation and structure of a new family of orthopalladated complexes
  作者：Jahar lal Pratihar、Nilkamal Maiti、Poulami Pattanayak、Surajit Chattopadhyay

  DOI：10.1016/j.poly.2005.05.022

  日期：2005.10

  Several 2-(arylazo)-N-alkyl aniline ligands, 1a-11a, have been prepared by the reaction between 2-(arylazo) aniline and the appropriate alkyl halide in the presence of K2CO3. Treatment of sodium tetrachloropallaclate with 1a-11a in methanol afforded the orthopalladated complexes 1b-11b, where the ligand is tridentate (C,N,N). The ligands and complexes were characterised from spectroscopic data and confirmed by X-ray studies. The X-ray Structure of 9b displayed an unsupported Pd(II)Pd-...(II) interaction (3.301 angstrom). (c) 2005 Elsevier Ltd. All rights reserved.