2,3,4,5-四氟苯甲酸甲酯 | 5292-42-2

• 物质功能分类: 有机原料 - 有机氟化合物 - 氟苯甲酸系列
• 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: 2,3,4,5-四氟苯甲酸甲酯
• 英文名称: 2,3,4,5-Tetrafluor-benzoesaeure-methylester
• 英文别名: Methyl 2,3,4,5-tetrafluorobenzoate
• CAS: 5292-42-2
• 化学式: C₈H₄F₄O₂
• 分子量: 208.112
• InChiKey: MAEQYZYOSFAUAF-UHFFFAOYSA-N

物化性质

• 沸点：
  187-188 °C
• 密度：
  1.443±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 海关编码：
  2916399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  2,3,4,5-四氟苯甲酸甲酯 在 硫酸 、 硝酸 作用下， 反应 2.5h， 以59%的产率得到methyl 2,3,4,5-tetrafluoro-6-nitrobenzoate
  参考文献：
  名称：

  Toward the development of radiolabeled fluorophenyl azide-based photolabeling reagents: synthesis and photolysis of iodinated 4-azidoperfluorobenzoates and 4-azido-3,5,6-trifluorobenzoates

  摘要：

  Two approaches for the incorporation of iodine into functionalized perfluorophenyl azides (PFPAs) were demonstrated by the synthesis of 3, 5, and 8, with the azido and iodo groups in the same aryl ring, and 14 and 15, with the azido and iodo groups in different aryl rings. These compounds opened the way for the incorporation of radioactive iodine into PFPAs and for their attachment to other molecules as photolabels. The syntheses of trifluorophenyl azides (TFPAs) 21-23 and iodide 20 provide two possible approaches for the incorporation of a tritium atom into fluorinated photolabels. Photolysis of azide 3 in cyclohexane gave 20% of CH insertion product and in Et2NH/cyclohexane gave 24% of NH insertion product. The relatively low yield of CH and NH insertion from 3 compared with the corresponding noniodinated PFPA 24 was probably due to the heavy atom effect. Photolysis of azide 15 in Et2NH/cyclohexane gave 41% of NH insertion product. Some photodeiodination was observed both with 3 and 15. Our results demonstrate that the iodinated PFPAs studied are much better at undergoing CH and NH insertion than their nonfluorinated analogues, thus constituting an improved series of iodinated photolabeling reagents. Photolysis of TFPA 22 in cyclohexane gave 37% of CH insertion product and in Et2NH/cyclohexane gave 63% of NH insertion product, results comparable to those of PFPA 24. Thus, the desirable photochemical characteristics of the PFPAs are largely preserved in the TFPAs.

  DOI：

  10.1021/jo00030a046
• 作为产物：
  描述：

  三辛胺 、 3,4,5,6-四氟苯酐 以 甲醇 为溶剂， 以92.3%的产率得到2,3,4,5-四氟苯甲酸甲酯
  参考文献：
  名称：

  Processes for producing tetrafluorophthalic anhydride and fluorobenzoic

  摘要：

  一种生产四氟邻苯二酐的方法，包括氯化四氯邻苯二酐以得到3,3,4,5,6,7-六氯-1-[3H]-异苯并呋喃酮，然后氟化它以得到3,4,5,6-四氟邻苯二酰二氟化物和/或3,3,4,5,6,7-六氟-1-[3H]-异苯并呋喃酮，然后进一步将四氟邻苯二酰二氟化物和/或六氟-1-[3H]-异苯并呋喃酮与无机碱或有机酸反应以得到四氟邻苯二酐。

  公开号：

  US05523476A1

文献信息

• 四并环类化合物及其制备方法和应用
  申请人：上海济煜医药科技有限公司

  公开号：CN112300195A

  公开（公告）日：2021-02-02

  本发明公开了式(Ⅰ)所示化合物、其光学异构体及其药效上可接受的盐，以及该化合物作为KRAS抑制剂的应用。
• Decarboxylative Polyfluoroarylation of Alkylcarboxylic Acids
  作者：Xiang Sun、Tobias Ritter

  DOI：10.1002/anie.202015596

  日期：2021.5.3

  Polyfluoroarenes are useful building blocks in several areas such as drug discovery, materials, and crop protection. Herein, we report the first polyfluoroarylation of aliphatic carboxylic acids via photoredox decarboxylation. The method proceeds with broad substrate scope and high functional group tolerance. Moreover, small complex molecules such as natural products and drugs can be modified by late‐stage

  多氟芳烃是药物发现、材料和作物保护等多个领域的有用组成部分。在此，我们报告了首次通过光氧化还原脱羧对脂肪族羧酸进行多氟芳基化。该方法具有广泛的底物范围和高官能团耐受性。此外，天然产物和药物等复杂小分子可以通过后期修饰进行修饰。
• Regioselective C-S Bond Formation Accomplished by Regioselective C-F Substitution of Polyfluoroarenes with Substituted Thiophenols
  作者：Qizhong Zhou、Bin Zhang、Haining Gu、Aiguo Zhong、Tieqi Du、Qiong Zhou、Yuyuan Ye、Zhengneng Jin、Huajiang Jiang、Rener Chen

  DOI：10.2174/157017812800167493

  日期：2012.3.1

  The nucleophilic aromatic substitution reaction of pentafluorobenzene, methyl 2,3,4,5-tetrafluorobenzoic acid ester and 1,2,4,5-tetrafluorobenzene with substituted thiophenols showed good regioselectivity while pentafluorobenzene gave high yields. The computational results suggest that the specificity difference between polyfluorobenzenes originates from their electronic properties.

  五氟苯，2,3,4,5-四氟苯甲酸甲酯和1,2,4,5-四氟苯与取代的苯酚的亲核芳族取代反应显示出良好的区域选择性，而五氟苯的收率很高。计算结果表明，多氟苯之间的特异性差异源自其电子性能。
• Polyfluoroaryl organometallic compounds. Part IX. Reactions of polyfluoroaryl-lithiums with dimethyl carbonate. Octafluorofluoren-9-one
  作者：R. D. Chambers、D. J. Spring

  DOI：10.1039/j39680002394

  日期：——

  Pentafluorophenyl-lithium reacts with dimethyl carbonate, under special conditions, to give a high yield of decafluorobenzophenone, but the corresponding reaction of o-bromotetrafluorophenyl-lithium is complicated by a novel exchange reaction, which is discussed. Octafluorofluoren-9-one is synthesised by reaction of 2,2′-dilithio-octafluorobiphenyl with dimethyl carbonate.

  在特殊条件下，五氟苯基锂与碳酸二甲酯反应可得到高产率的十氟二苯甲酮，但邻溴四氟苯基锂的相应反应由于新型的交换反应而变得复杂，对此进行了讨论。八氟芴-9-one是通过2,2'-二硫代-八氟联苯与碳酸二甲酯的反应合成的。
• Process for producing tetrafluorophthalic anhydride
  申请人：Asahi Glass Company Ltd.

  公开号：US05648504A1

  公开（公告）日：1997-07-15

  A process for producing tetrafluorophthalic anhydride, which comprises chlorinating tetrachlorophthalic anhydride to obtain 3,3,4,5,6,7-hexachloro-1-[3H]-isobenzofuranone, then fluorinating it to obtain 3,4,5,6-tetrafluorophthaloyldifluoride and/or 3,3,4,5,6,7-hexafluoro-1-[3]-isobenzofuranone, and further reacting the tetrafluorophthalolyldifluoride and/or the hexafluoro-1-[3H]-isobenzofuranone with an inorganic base or an organic acid to obtain tetrafluorophthalic anhydride.

  一种生产四氟邻苯二甲酸酐的方法，包括将四氯邻苯二甲酸酐氯化以得到3,3,4,5,6,7-六氯-1-[3H]-异苯并呋喃酮，然后氟化它以得到3,4,5,6-四氟邻苯二甲酰二氟化物和/或3,3,4,5,6,7-六氟-1-[3]-异苯并呋喃酮，然后进一步将四氟邻苯二甲酰二氟化物和/或六氟-1-[3H]-异苯并呋喃酮与无机碱或有机酸反应以得到四氟邻苯二甲酸酐。