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4-硝基氟苯

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4-硝基氟苯
识别
CAS号 350-46-9  checkY
性质
化学式 C6H4FNO2
摩尔质量 141.1 g·mol−1
密度 1.33 g·cm−3(20 °C)[1]
熔点 27 °C(300 K)[1]
21 °C(294 K)[2]
沸点 206—207 °C(479—480 K)[1]
205 °C(478 K)[2]
相关物质
相关化学品 4-硝基氯苯
4-硝基溴苯
4-硝基碘苯
2-硝基氟苯
3-硝基氟苯
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

4-硝基氟苯是一种有机化合物,化学式为C6H4FNO2

制备

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4-硝基氟苯可由4-硝基氯苯氟化钾PPNCl英语Bis(triphenylphosphine)iminium chloride催化下于二甲基亚砜中进行卤素交换反应制得。[3]

硝酸三氟乙酸酐在Hβ沸石的存在下对氟苯进行硝化,可以得到4-硝基氟苯,副产物为2-硝基氟苯,占比8%,若在反应体系中另加入乙酸酐,可使邻位的副产物降至1%以下。[4]

性质

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催化下,氢气硼氢化钠可将其还原为4-氟苯胺[5][6]它和N-甲基哌嗪发生偶联反应,可以得到1-甲基-4-(4-硝基苯基)哌嗪。[7]

参考文献

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  1. ^ 1.0 1.1 1.2 "Hazardous Substances Data Bank" data were obtained from the National Library of Medicine (US). Retrieved from SciFinder. [2021-11-24].
  2. ^ 2.0 2.1 "PhysProp" data were obtained from Syracuse Research Corporation of Syracuse, New York (US). Retrieved from SciFinder. [2021-11-24].
  3. ^ Marie-Agnès Lacour, Maria Zablocka, Carine Duhayon, Jean-Pierre Majoral, Marc Taillefer. Efficient Phosphorus Catalysts for the Halogen-Exchange (Halex) Reaction. Advanced Synthesis & Catalysis. 2008-11-14, 350 (17): 2677–2682 [2021-11-24]. doi:10.1002/adsc.200800428. (原始内容存档于2021-11-24) (英语). 
  4. ^ Keith Smith, Tracy Gibbins, Ross W. Millar, Robert P. Claridge. A novel method for the nitration of deactivated aromatic compounds †. Journal of the Chemical Society, Perkin Transactions 1. 2000, (16): 2753–2758 [2021-11-24]. doi:10.1039/b002158j. 
  5. ^ Qingjie Tang, Ziliang Yuan, Shiwei Jin, Kaiyue Yao, Hanmin Yang, Quan Chi, Bing Liu. Biomass-derived carbon-supported Ni catalyst: an effective heterogeneous non-noble metal catalyst for the hydrogenation of nitro compounds. Reaction Chemistry & Engineering. 2020, 5 (1): 58–65 [2021-11-24]. ISSN 2058-9883. doi:10.1039/C9RE00366E (英语). 
  6. ^ Mahsa Niakan, Zahra Asadi. Selective Reduction of Nitroarenes Catalyzed by Sustainable and Reusable DNA-supported Nickel Nanoparticles in Water at Room Temperature. Catalysis Letters. 2019-08, 149 (8): 2234–2246 [2021-11-24]. ISSN 1011-372X. doi:10.1007/s10562-019-02741-7 (英语). 
  7. ^ Pu Xiang, Tian Zhou, Liang Wang, Chang-Yan Sun, Jing Hu, Ying-Lan Zhao, Li Yang. Novel Benzothiazole, Benzimidazole and Benzoxazole Derivatives as Potential Antitumor Agents: Synthesis and Preliminary in Vitro Biological Evaluation. Molecules. 2012-01-17, 17 (1): 873–883 [2021-11-24]. ISSN 1420-3049. PMC 6268746可免费查阅. PMID 22252503. doi:10.3390/molecules17010873. (原始内容存档于2022-03-13) (英语).