3-fluoro-2-(2-fluorophenylamino)benzoic acid | 203568-52-9

• 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: 3-fluoro-2-(2-fluorophenylamino)benzoic acid
• 英文别名: Benzoic acid, 3-fluoro-2-(3-fluorophenylamino)-；3-fluoro-2-(2-fluoroanilino)benzoic acid
• CAS: 203568-52-9
• 化学式: C₁₃H₉F₂NO₂
• 分子量: 249.217
• InChiKey: AZIAOUXXPIMDPH-UHFFFAOYSA-N

物化性质

• 沸点：
  328.3±42.0 °C(Predicted)
• 密度：
  1.412±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 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：
  5

反应信息

• 作为反应物：
  描述：

  3-fluoro-2-(2-fluorophenylamino)benzoic acid 在 三氯氧磷 作用下， 以 氯仿 为溶剂， 反应 4.0h， 生成 N'-(4,5-difluoroacridin-9-yl)-4-methylbenzenesulfonohydrazide
  参考文献：
  名称：

  4,5-bis(diphenylphosphino)acridine: A new type of tridentate phosphorus-nitrogen-phosphorus ligands

  摘要：

  Reaction of 4,5-difluoroacridine (8) with two equivalents of potassium diphenylphosphide (Ph2PK) yielded the title compound 3. Contrarily, diphenylphosphine (Ph2PH) reacted with 8 under addition, and 4,5-difluoro-9-diphenyl-9,10-dihydroacridine (12) was obtained. Compound 8 was prepared from 2-amino-3-fluorobenzoic acid (13) in a four step synthesis. As it is shown by the preparation of the metal complexes 4,5-bis(diphenylphosphino)acridine-palladium dichloride (16) and 4,5-bis(diphenylphosphino)acridine-molybdenum tricarbonyl (17), compound 3 is capable of acting as a tridentate PNP ligand which coordinates transition metals in an approximately "T-shaped" planar coordination geometry. Single crystal X-ray structure analyses are reported for 3 and 17. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10790-0
• 作为产物：
  描述：

  2-氟碘苯 、 2-氨基-3-氟苯甲酸 在 铜 、 potassium carbonate 作用下， 以 环己醇 为溶剂， 反应 12.0h， 以71%的产率得到3-fluoro-2-(2-fluorophenylamino)benzoic acid
  参考文献：
  名称：

  铁钳复合物催化炔烃的环境友好的电子选择性半氢化

  摘要：

  消除氢化：第一次，铁催化剂提供了炔烃化学和立体选择性半加氢成E烯烃的能力。这种新型的a啶基PNP铁钳催化剂可有效地进行这种原子经济的反应，在温和，中性，环境友好的反应条件下表现出优异的官能团耐受性。

  DOI：

  10.1002/anie.201306629

文献信息

• Catalysts made from transition metal compounds and 4, 5-diphosphinoacridine-ligands
  申请人：Studiengesellschaft Kohle mbH

  公开号：US06290926B1

  公开（公告）日：2001-09-18

  The present invention relates to the preparation of novel catalysts made from transition metal compounds and “tridentate” 4,5-diphosphinoacridine ligands (“acriphos”). The novel ligands employed herein are diphosphine compounds of 4,5-disubstituted acridine which coordinate transition metals in a three-fold way with the two phosphorus atoms and the acridine nitrogen. The invention also relates to the use of the novel catalysts for the catalysis of carbon monoxide conversion via the water-gas shift reaction (WGSR: CO+H2O→CO2+H2) and for the catalysis of the following reactions: hydroformylation, carbonylation, carboxylation, hydrogenation, hydrocyanogenation, hydrosilylation, polymerization, isomerization, cross-couplings and metathesis. The invention further relates to heretofore unknown syntheses of the 4,5-diphosphinoacridines through the reaction of 4,5-difluoroacridine with alkali metal phosphides [R2P−M+(M+═Li+, Na+, K+, Rb+, Cs+, preferably K+)] or through the reaction of 4,5-dibromoacridine with chlorophosphines (R2PCl) and magnesium, and to the preparation of 4,5-difluoroacridine and 4,5-dibromoacridine.

  本发明涉及使用过渡金属化合物和“三齿”4,5-二膦基蒽啉配体（“acriphos”）制备新型催化剂的方法。本发明所采用的新型配体是4,5-二取代蒽啉的二膦烷化合物，其通过两个磷原子和蒽啉氮以三重方式配位于过渡金属上。本发明还涉及使用新型催化剂催化一氧化碳转化为水煤气变换反应（WGSR: CO+H2O→CO2+H2）以及以下反应：氢甲酰化、羰基化、羧化、加氢、氢氰化、硅氢化、聚合、异构化、交叉偶联和重排反应。本发明还涉及通过4,5-二氟蒽啉与碱金属磷化物（R2P−M+(M+═Li+, Na+, K+, Rb+, Cs+，最好是K+)]反应或通过4,5-二溴蒽啉与氯膦（R2PCl）和镁反应而得到4,5-二膦基蒽啉的未知合成方法，并制备了4,5-二氟蒽啉和4,5-二溴蒽啉。
• Iron Pincer Complex Catalyzed, Environmentally Benign,<i>E</i>-Selective Semi-Hydrogenation of Alkynes
  作者：Dipankar Srimani、Yael Diskin-Posner、Yehoshoa Ben-David、David Milstein

  DOI：10.1002/anie.201306629

  日期：2013.12.23

  Ironing out hydrogenation: For the first time, an iron catalyst provided chemo‐ and stereo‐selective semi‐hydrogenation of alkynes to E‐alkenes. This efficient, atom‐economical reaction is catalyzed by a novel acridine‐based PNP iron pincer catalyst and exhibits excellent functional group tolerance under mild, neutral, environmentally benign reaction conditions.

  消除氢化：第一次，铁催化剂提供了炔烃化学和立体选择性半加氢成E烯烃的能力。这种新型的a啶基PNP铁钳催化剂可有效地进行这种原子经济的反应，在温和，中性，环境友好的反应条件下表现出优异的官能团耐受性。
• 4,5-bis(diphenylphosphino)acridine: A new type of tridentate phosphorus-nitrogen-phosphorus ligands
  作者：Stefan Hillebrand、Beata Bartkowska、Joachim Bruckmann、Carl Krüger、Matthias W. Haenel

  DOI：10.1016/s0040-4039(97)10790-0

  日期：1998.2

  Reaction of 4,5-difluoroacridine (8) with two equivalents of potassium diphenylphosphide (Ph2PK) yielded the title compound 3. Contrarily, diphenylphosphine (Ph2PH) reacted with 8 under addition, and 4,5-difluoro-9-diphenyl-9,10-dihydroacridine (12) was obtained. Compound 8 was prepared from 2-amino-3-fluorobenzoic acid (13) in a four step synthesis. As it is shown by the preparation of the metal complexes 4,5-bis(diphenylphosphino)acridine-palladium dichloride (16) and 4,5-bis(diphenylphosphino)acridine-molybdenum tricarbonyl (17), compound 3 is capable of acting as a tridentate PNP ligand which coordinates transition metals in an approximately "T-shaped" planar coordination geometry. Single crystal X-ray structure analyses are reported for 3 and 17. (C) 1998 Elsevier Science Ltd. All rights reserved.