八氟萘

八氟萘
識別
CAS號	313-72-4
SMILES	Fc1c(F)c(F)c(F)c2c1c(F)c(F)c(F)c2F;
性質
化學式	C10F8
摩爾質量	272.09 g·mol−1
密度	2.07 g·cm−3
熔點	86—87 °C（359—360 K）
沸點	207—209 °C（480—482 K）
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

八氟萘是一種有機化合物，為萘的氫原子全部被氟取代的化合物，化學式為C₁₀F₈。它是單斜晶系的晶體，空間群P2₁/c。^[3]它可由八氯萘和氟化鉀在環丁碸中於235 °C反應製得。^[4]全氟十氫萘在催化劑和氯化汞的存在下可以被鎂或鋁還原為八氟萘。^[5]在氯化銨的存在下，它可以被鋅粉在氨水中還原為1,2,4,5,6,8-六氟萘。^[6]

參考文獻

^ Robbins, Andrew J.; Ng, William T. K.; Jochym, Dominik; Keal, Thomas W.; Clark, Stewart J.; Tozer, David J.; Hodgkinson, Paul. Combining insights from solid-state NMR and first principles calculation: applications to the 19F NMR of octafluoronaphthalene. Physical Chemistry Chemical Physics. 2007, 9 (19): 2389. ISSN 1463-9076. doi:10.1039/b701291h.
^ ^2.0 ^2.1 Yakobson, G. G.; Shteingarts, V. D.; Vorozhtsov, N. N., Jr. Synthesis of octafluoronaphthalene and decafluorodiphenyl. Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1964. 8: 1551. ISSN: 0002-3353.
^ Bagryanskaya, Irina Yu.; Gatilov, Yuri V.; Lork, Enno; Mews, Rüdiger; Shakirov, Makhmut M.; Watson, Paul G.; Zibarev, Andrey V. Molecular complexes of octafluoronaphthalene with acyclic and heterocyclic sulfur–nitrogen compounds. Journal of Fluorine Chemistry. 2002, 116 (2): 149–156. ISSN 0022-1139. doi:10.1016/S0022-1139(02)00127-6.
^ Fuller, G. 1165. Preparation of polyfluoroaromatic compounds by the reaction of perhalogeno-aromatic compounds with potassium fluoride in sulpholan. Journal of the Chemical Society (Resumed). 1965: 6264. ISSN 0368-1769. doi:10.1039/jr9650006264.
^ Jaqueline L. Kiplinger, Thomas G. Richmond. Group IV Metallocene-Mediated Synthesis of Fluoroaromatics via Selective Defluorination of Saturated Perfluorocarbons. Journal of the American Chemical Society. 1996-01, 118 (7): 1805–1806 [2021-01-09]. ISSN 0002-7863. doi:10.1021/ja952563u （英語）.
^ Sergey S. Laev, Vitalii D. Shteingarts. Reductive defluorination of perfluoroarenes by zinc in aqueous ammonia. Journal of Fluorine Chemistry. 1998-08, 91 (1): 21–23 [2021-01-09]. doi:10.1016/S0022-1139(98)00194-8. （原始內容存檔於2018-06-14）（英語）.

[1] Robbins, Andrew J.; Ng, William T. K.; Jochym, Dominik; Keal, Thomas W.; Clark, Stewart J.; Tozer, David J.; Hodgkinson, Paul. Combining insights from solid-state NMR and first principles calculation: applications to the 19F NMR of octafluoronaphthalene. Physical Chemistry Chemical Physics. 2007, 9 (19): 2389. ISSN 1463-9076. doi:10.1039/b701291h.

[Yakobson-2] 2.0 ^2.1 Yakobson, G. G.; Shteingarts, V. D.; Vorozhtsov, N. N., Jr. Synthesis of octafluoronaphthalene and decafluorodiphenyl. Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1964. 8: 1551. ISSN: 0002-3353.

[3] Bagryanskaya, Irina Yu.; Gatilov, Yuri V.; Lork, Enno; Mews, Rüdiger; Shakirov, Makhmut M.; Watson, Paul G.; Zibarev, Andrey V. Molecular complexes of octafluoronaphthalene with acyclic and heterocyclic sulfur–nitrogen compounds. Journal of Fluorine Chemistry. 2002, 116 (2): 149–156. ISSN 0022-1139. doi:10.1016/S0022-1139(02)00127-6.

[4] Fuller, G. 1165. Preparation of polyfluoroaromatic compounds by the reaction of perhalogeno-aromatic compounds with potassium fluoride in sulpholan. Journal of the Chemical Society (Resumed). 1965: 6264. ISSN 0368-1769. doi:10.1039/jr9650006264.

[5] Jaqueline L. Kiplinger, Thomas G. Richmond. Group IV Metallocene-Mediated Synthesis of Fluoroaromatics via Selective Defluorination of Saturated Perfluorocarbons. Journal of the American Chemical Society. 1996-01, 118 (7): 1805–1806 [2021-01-09]. ISSN 0002-7863. doi:10.1021/ja952563u （英語）.

[6] Sergey S. Laev, Vitalii D. Shteingarts. Reductive defluorination of perfluoroarenes by zinc in aqueous ammonia. Journal of Fluorine Chemistry. 1998-08, 91 (1): 21–23 [2021-01-09]. doi:10.1016/S0022-1139(98)00194-8. （原始內容存檔於2018-06-14）（英語）.

[1]

[2]

[3]

[4]

[5]

[6]