4-anilino-3,5-dinitro-benzoic acid | 7221-24-1

• 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: 4-anilino-3,5-dinitro-benzoic acid
• 英文别名: 4-Anilino-3,5-dinitro-benzoesaeure；2.6-Dinitro-diphenylamin-carbonsaeure-(4)；2,6-dinitrodiphenylamine-4-carboxylic acid；2.6-Dinitro-4-carboxy-diphenylamin；3,5-Dinitro-4-(phenylamino)benzoic acid；4-anilino-3,5-dinitrobenzoic acid
• CAS: 7221-24-1
• 化学式: C₁₃H₉N₃O₆
• 分子量: 303.231
• InChiKey: MDPOBYVJWFEBRC-UHFFFAOYSA-N

物化性质

• 沸点：
  461.7±45.0 °C(Predicted)
• 密度：
  1.581±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  141
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-anilino-3,5-dinitro-benzoic acid 在 五氯化磷 、 苯 作用下， 生成 4-anilino-3,5-dinitro-benzoic acid ethyl ester
  参考文献：
  名称：

  Lindemann; Wessel, Chemische Berichte, 1925, vol. 58, p. 1230

  摘要：

  DOI：
• 作为产物：
  描述：

  4-溴-3-硝基甲苯 在 potassium dichromate 、 硫酸 、 硝酸 作用下， 生成 4-anilino-3,5-dinitro-benzoic acid
  参考文献：
  名称：

  Jackson; Ittner, American Chemical Journal, 1897, vol. 19, p. 14

  摘要：

  DOI：

文献信息

• Micellar catalysis of organic reactions. 29. SNAr reactions with neutral nucleophiles
  作者：Trevor J. Broxton、Victor Marcou

  DOI：10.1021/jo00003a026

  日期：1991.2

  The reaction of a number of nitroactivated halobenzoates (1-4) with some primary and tertiary amines has been studied in the presence of micelles of cetyltrimethylammonium bromide (CTAB) and in water. With primary amines aminodehalogenation was observed, and it was found that if the reaction center of the aromatic substrate was located at the micelle water interface (compounds 1 and 2) the reaction was catalyzed by CTAB, but if the reaction center was more deeply buried into the micellar interior the reaction with aniline was inhibited by micelles of CTAB (compounds 3 and 4), while CTAB had little effect on the reaction of n-propylamine with compound 4. With the more sterically bulky tertiary amines, hydroxydehalogenation was observed rather than amino-dehalogenation, and the reactions were all catalyzed by CTAB, but for the substrate with a more deeply buried reaction center (compound 4), the catalysis was stronger than for that with a reaction center at or near the interface (compound 2). The mechanism of hydroxydehalogenation was found to be specific base catalysis by the tertiary amine. Thus the observation of micellar catalysis or inhibition of these reactions depends on the orientation of the organic substrate within the micellar aggregate and the reaction product, amine or phenol, depends on the steric bulk of the amine at least for the compounds investigated here which contain two substitutents ortho to the reaction center.
• Preston et al., Journal of the Chemical Society, 1942, p. 500,503
  作者：Preston et al.

  DOI：——

  日期：——
• BROXTON, TREVOR J.;MARCOU, VICTOR, J. ORG. CHEM., 56,(1991) N, C. 1041-1044
  作者：BROXTON, TREVOR J.、MARCOU, VICTOR

  DOI：——

  日期：——
• US4756715A
  申请人：——

  公开号：US4756715A

  公开（公告）日：1988-07-12
• Lindemann; Wessel, Chemische Berichte, 1925, vol. 58, p. 1230
  作者：Lindemann、Wessel

  DOI：——

  日期：——