4-硝基氟苯

化合物

4-硝基氟苯是一種有機化合物,化學式為C6H4FNO2

4-硝基氟苯
識別
CAS號 350-46-9  checkY
性質
化學式 C6H4FNO2
摩爾質量 141.1 g·mol−1
密度 1.33 g·cm−3(20 °C)[1]
熔點 27 °C(300 K)[1]
21 °C(294 K)[2]
沸點 206—207 °C(479—480 K)[1]
205 °C(478 K)[2]
相關物質
相關化學品 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
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。

製備

編輯

4-硝基氟苯可由4-硝基氯苯氟化鉀PPNCl英語Bis(triphenylphosphine)iminium chloride催化下於二甲基亞碸中進行鹵素交換反應製得。[3]

硝酸三氟乙酸酐在Hβ沸石的存在下對氟苯進行硝化,可以得到4-硝基氟苯,副產物為2-硝基氟苯,占比8%,若在反應體系中另加入乙酸酐,可使鄰位的副產物降至1%以下。[4]

性質

編輯

催化下,氫氣硼氫化鈉可將其還原為4-氟苯胺[5][6]它和N-甲基哌嗪發生偶聯反應,可以得到1-甲基-4-(4-硝基苯基)哌嗪。[7]

參考文獻

編輯
  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. (原始內容存檔於2021-11-24) (英語). 
  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 (英語). 
  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 (英語). 
  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 . PMID 22252503. doi:10.3390/molecules17010873. (原始內容存檔於2022-03-13) (英語).