2-溴-3-硝基苯甲酰胺 | 35757-19-8

• 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: 2-溴-3-硝基苯甲酰胺
• 英文名称: 2-bromo-3-nitrobenzamide
• 英文别名: 2-bromo-3-nitro-benzoic acid amide；2-Brom-3-nitro-benzoesaeure-amid；2-Brom-3-nitro-benzamid
• CAS: 35757-19-8
• 化学式: C₇H₅BrN₂O₃
• 分子量: 245.032
• InChiKey: TXFBJRKUCSPKPD-UHFFFAOYSA-N

物化性质

• 熔点：
  170-171 °C
• 沸点：
  287.8±25.0 °C(Predicted)
• 密度：
  1.799±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  88.9
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  2-溴-3-硝基苯甲酰胺 在 copper(l) iodide 、 sodium azide 、 乙醇 、 caesium carbonate 作用下， 以71%的产率得到2-氨基-3-硝基苯甲酰胺
  参考文献：
  名称：

  Copper-Catalyzed Direct Amination of Ortho-Functionalized Haloarenes with Sodium Azide as the Amino Source

  摘要：

  A simple copper-catalyzed direct amination of ortho-functionalized haloarenes (2-halobenzoic acid, 2-halobenzamide, and N-(2-bromophenyl)acetamide derivatives) has been developed with use of NaN3 as the amino source in ethanol, and the corresponding ortho-functionalized aromatic amines were synthesized in good to excellent yields. The protocol undergoes one-pot Ullmann-type coupling of ortho-functionalized haloarenes with NaN3 to lead to ortho-functionalized azidoarenes, followed by reduction with ethanol.

  DOI：

  10.1021/jo100345t
• 作为产物：
  描述：

  2-溴-3-硝基苯甲酸 生成 2-溴-3-硝基苯甲酰胺
  参考文献：
  名称：

  Nucleophilic Substitution Reactions of 1-Halogeno-4-COR-2-nitrobenzenes and 1-Halogeno-6-COR-2-nitrobenzenes with Sodium Benzenethiolate and Piperidine. Can an “Inverted Built-In Solvation” Be Responsible for the Peculiar Activation by an o-Carboxamido Group in S_NAr Reactions with an Anionic Nucleophile?

  摘要：

  A kinetic study of the title reactions has allowed an interpretation of the higher efficiency of an o-carboxamido group with respect to an o-carbomethoxy group in activating the benzenethiolate-dehalogenation reactions in methanol (k(CONH2)/k(CO2Me) 2.2-3.0) as due to an interaction between the anionic nucleophile and the hydrogen atoms of the carboxamido group. An inversion of the activating power of the two groups (kCONH(2)/k(CO2Me) 0.14) in the reactions with the same nucleophile has been observed when they are in a para-position. Moreover, for piperidino-dehalogenation reactions in methanol k(CONH2)/k(CO2Me) ratios less than unity (0.2-0.6) have been observed independently of the position (ortho or para) of the carboxamido and carbomethoxy groups with respect to the reaction center.

  DOI：

  10.1021/jo961040h

文献信息

• SOME DERIVATIVES OF PHENOTHIAZINE. II.¹
  作者：ALFRED BURGER、A. CHANDLER SCHMALZ

  DOI：10.1021/jo01376a020

  日期：1954.11
• Depoorter; Nys, 1958, p. Bd 2,S.473
  作者：Depoorter、Nys

  DOI：——

  日期：——
• Depoorter; Nys, Ind. chim. belge Sonderband 31. Congr. int. Chim. ind. Luettich 1958 Bd. 2, S. 473, 474
  作者：Depoorter、Nys

  DOI：——

  日期：——
• Copper-Catalyzed Direct Amination of Ortho-Functionalized Haloarenes with Sodium Azide as the Amino Source
  作者：Haibo Zhao、Hua Fu、Renzhong Qiao

  DOI：10.1021/jo100345t

  日期：2010.5.21

  A simple copper-catalyzed direct amination of ortho-functionalized haloarenes (2-halobenzoic acid, 2-halobenzamide, and N-(2-bromophenyl)acetamide derivatives) has been developed with use of NaN3 as the amino source in ethanol, and the corresponding ortho-functionalized aromatic amines were synthesized in good to excellent yields. The protocol undergoes one-pot Ullmann-type coupling of ortho-functionalized haloarenes with NaN3 to lead to ortho-functionalized azidoarenes, followed by reduction with ethanol.
• Nucleophilic Substitution Reactions of 1-Halogeno-4-COR-2-nitrobenzenes and 1-Halogeno-6-COR-2-nitrobenzenes with Sodium Benzenethiolate and Piperidine. Can an “Inverted Built-In Solvation” Be Responsible for the Peculiar Activation by an <i>o</i>-Carboxamido Group in S_NAr Reactions with an Anionic Nucleophile?
  作者：Caterina Arnone、Giovanni Consiglio、Vincenzo Frenna、Domenico Spinelli

  DOI：10.1021/jo961040h

  日期：1997.5.1

  A kinetic study of the title reactions has allowed an interpretation of the higher efficiency of an o-carboxamido group with respect to an o-carbomethoxy group in activating the benzenethiolate-dehalogenation reactions in methanol (k(CONH2)/k(CO2Me) 2.2-3.0) as due to an interaction between the anionic nucleophile and the hydrogen atoms of the carboxamido group. An inversion of the activating power of the two groups (kCONH(2)/k(CO2Me) 0.14) in the reactions with the same nucleophile has been observed when they are in a para-position. Moreover, for piperidino-dehalogenation reactions in methanol k(CONH2)/k(CO2Me) ratios less than unity (0.2-0.6) have been observed independently of the position (ortho or para) of the carboxamido and carbomethoxy groups with respect to the reaction center.