3,5-二溴-2-氟苯硼酸 | 1072951-82-6

• 物质功能分类: 有机原料 - 有机氟化合物 - 氟苯硼酸系列
• 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: 3,5-二溴-2-氟苯硼酸
• 英文名称: (3,5-Dibromo-2-fluorophenyl)boronic acid
• CAS: 1072951-82-6
• 化学式: C₆H₄BBr₂FO₂
• 分子量: 297.714
• InChiKey: IOOXXDZRFJBCLR-UHFFFAOYSA-N

物化性质

• 熔点：
  256-275 °C
• 沸点：
  373.0±52.0 °C(Predicted)
• 密度：
  2.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.03
• 重原子数：
  12
• 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：
  40.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• WGK Germany：
  3
• 海关编码：
  2931900090
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340+P312,P305+P351+P338,P332+P313,P337+P313,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  3,5-二溴-2-氟苯硼酸 在 2,4-二硝基苯基羟胺 作用下， 以 甲苯 为溶剂， 反应 72.0h， 以54%的产率得到3,5-dibromo-2-fluorobenzenamine
  参考文献：
  名称：

  Elusive Metal-Free Primary Amination of Arylboronic Acids: Synthetic Studies and Mechanism by Density Functional Theory

  摘要：

  Herein, we disclose the first metal-free synthesis of primary aromatic amines from arylboronic acids, a reaction that has eluded synthetic chemists for decades. This remarkable transformation affords structurally diverse primary arylamines in good chemical yields, including a variety of halogenated primary anilines that often cannot be prepared via transition-metal-catalyzed amination. The reaction is operationally simple, requires only a slight excess of aminating agent, proceeds under neutral or basic conditions, and, importantly, can be scaled up to provide multigram quantities of primary anilines. Density functional calculations reveal that the most likely mechanism involves a facile 1,2-aryl migration and that the presence of an ortho nitro group in the aminating agent plays a critical role in lowering the free energy barrier of the 1,2-aryl migration step.

  DOI：

  10.1021/ja309637r

文献信息

• Development of progesterone receptor antagonists from 1,2-dihydrochromeno[3,4-f]quinoline agonist pharmacophore
  作者：Lin Zhi、Josef D Ringgenberg、James P Edwards、Christopher M Tegley、Sarah J West、Barbara Pio、Mehrnouch Motamedi、Todd K Jones、Keith B Marschke、Dale E Mais、William T Schrader

  DOI：10.1016/s0960-894x(03)00256-7

  日期：2003.6

  A series of 1,2-dihydrochromeno[3,4-f]quinoline derivatives was synthesized and tested in biological assays to evaluate the nonsteroidal progesterone receptor modulator pharmacophore (4) as antiprogestins. A number of potent analogues were identified by modification of the substituents at the D-ring. (C) 2003 Elsevier Science Ltd. All rights reserved.