5-溴-2-苯氨基苯甲酸 | 82762-60-5

• 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: 5-溴-2-苯氨基苯甲酸
• 英文名称: 5-Bromo-N-phenylanthranilic acid
• 英文别名: N-phenyl-5-bromoanthranilic acid；5-Bromo-2-(phenylamino)benzoic acid；2-anilino-5-bromobenzoic acid
• CAS: 82762-60-5
• 化学式: C₁₃H₁₀BrNO₂
• 分子量: 292.132
• InChiKey: DUKWALMEUHYKDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  17
• 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：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2922499990

反应信息

• 作为反应物：
  描述：

  5-溴-2-苯氨基苯甲酸 在 lithium aluminium tetrahydride 、 sodium hydride 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.25h， 生成 5-bromo-2-(N-methylanilino)benzaldehyde
  参考文献：
  名称：

  Sc(OTf)₃-Catalyzed Dehydrogenative Cyclization for Synthesis of N-Methylacridones

  摘要：

  A novel method has been developed for the synthesis of substituted N-methylacridones from 2-(N-methyl-N-phenylamino)benzaldehydes via dehydrogenative cyclization. This transformation involves two primary processes: the aldehyde first coordinates with Sc(OTf)(3) and induces the aromatic electrophilic substitution (SEAr) reaction to form the active intermediate N-methyl-acridin-9-ol, which is then quickly oxidized in situ to afford the acridones. Furthermore, the procedure involved is both environmental friendly and atom efficient; H2O is the only byproduct in this reaction.

  DOI：

  10.1021/ol400371h
• 作为产物：
  描述：

  2-氨基-5-溴苯甲酸 在 盐酸 、 potassium carbonate 、 copper(II) oxide 、 copper(I) bromide 、 sodium nitrite 作用下， 反应 7.0h， 生成 5-溴-2-苯氨基苯甲酸
  参考文献：
  名称：

  Khalifa; Osman; Ibrahim, Pharmazie, 1982, vol. 37, # 2, p. 115 - 117

  摘要：

  DOI：

文献信息

• Regioselective Copper-Catalysed Amination of Halobenzoic Acids using Aromatic Amines
  作者：Mohan Babu Maradolla、Amaravathi Mandha、Chandra Mouli Garimella

  DOI：10.3184/030823407x255597

  日期：2007.10

  Copper dipyridine dichloride (CuPy2Cl2) has been found to be an efficient catalyst for the synthesis of N-arylanthranilic acids from ortho halobenzoic acids and aromatic amines under microwave irradiation. Some of the advantages of this method are high chemoselectivity, ease of operation, less reaction times and high yields. (61–98%).

  已发现二氯化二吡啶铜 (CuPy2Cl2) 是在微波辐射下由邻卤苯甲酸和芳香胺合成 N-芳基邻氨基苯甲酸的有效催化剂。这种方法的一些优点是高化学选择性、易于操作、反应时间短和收率高。(61–98%)。
• Regioselective Copper-Catalyzed Amination of Bromobenzoic Acids Using Aliphatic and Aromatic Amines
  作者：Christian Wolf、Shuanglong Liu、Xuefeng Mei、Adam T. August、Michael D. Casimir

  DOI：10.1021/jo060034a

  日期：2006.4.1

  A chemo- and regioselective copper-catalyzed cross-coupling procedure for amination of 2-bromobenzoic acids is described. The method eliminates the need for acid protection and produces N-aryl and N-alkyl anthranilic acid derivatives in up to 99% yield. N-(1-Pyrene)anthranilic acid has been employed in metal ion-selective fluorosensing. Titration experiments showed that this pyrene-derived amino acid forms an equimolar complex with Hg(II) in water resulting in selective fluorescence quenching even in the presence of other metal ions such as Zn(II) and Cd(II).
• KHALIFA, M.;OSMAN, A. N.;IBRAHIM, M. G.;OSSMAN, A. -R. E.;ISMAIL, M. A., PHARMAZIE, 1982, 37, N 2, 115-117
  作者：KHALIFA, M.、OSMAN, A. N.、IBRAHIM, M. G.、OSSMAN, A. -R. E.、ISMAIL, M. A.

  DOI：——

  日期：——
• KHALIFA, M.;OSMAN, A. N.;IBRAHIM, M. G.;OSSMAN, A. E.;ISMAIL, M. A., EGYPT. J. CHEM., 1982, 25, N 3, 285-291
  作者：KHALIFA, M.、OSMAN, A. N.、IBRAHIM, M. G.、OSSMAN, A. E.、ISMAIL, M. A.

  DOI：——

  日期：——
• Sc(OTf)₃-Catalyzed Dehydrogenative Cyclization for Synthesis of <i>N</i>-Methylacridones
  作者：Xi-An Li、Hong-Li Wang、Shang-Dong Yang

  DOI：10.1021/ol400371h

  日期：2013.4.19

  A novel method has been developed for the synthesis of substituted N-methylacridones from 2-(N-methyl-N-phenylamino)benzaldehydes via dehydrogenative cyclization. This transformation involves two primary processes: the aldehyde first coordinates with Sc(OTf)(3) and induces the aromatic electrophilic substitution (SEAr) reaction to form the active intermediate N-methyl-acridin-9-ol, which is then quickly oxidized in situ to afford the acridones. Furthermore, the procedure involved is both environmental friendly and atom efficient; H2O is the only byproduct in this reaction.