八氯萘

八氯萘
識別
CAS號	2234-13-1
SMILES	Clc1c(Cl)c(Cl)c(Cl)c2c1c(Cl)c(Cl)c(Cl)c2Cl;
性質
化學式	C10Cl8
摩爾質量	403.73 g·mol−1
外觀	黃色固體
密度	2.0 g·cm−3
熔點	197.5—198 °C（470.6—471.1 K）
沸點	440 °C（713 K）
溶解性（水）	難溶
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

八氯萘是一種有機化合物，化學式為C₁₀Cl₈。它是難溶於水的黃色固體^[1]^[2]，於2015年作為多氯萘列入斯德哥爾摩公約附錄A和附錄C中。^[3]它可由萘在磺酰氯中在氯化鐵的存在下和氯氣反應製得^[4]；或由萘和氯氣在五氯化銻的存在下於150~210 °C反應得到。^[5]它和乙硫醇鈉在DMF中反應，可以得到八(乙硫基)萘。^[6]它在45~50 °C可以被五氟化釩氧化，得到C₁₀Cl₈F₈和VF₄。^[7]

參見

八氟萘，C₁₀F₈
八溴萘，C₁₀Br₈，CAS號22245-33-6，萘汞化後和KBr₃反應得到^[8]
八碘萘，C₁₀I₈，CAS號701977-35-7，萘汞化後和KI₃反應得到^[9]

參考文獻

^ ^1.0 ^1.1 Octachlornaphthalin. GESTIS-Stoffdatenbank. [2020-03-10].
^ Jeanne Mager Stellman. Encyclopaedia of Occupational Health and Safety. International Labour Organization. 1998: 298. ISBN 978-92-2-109817-1.
^ All POPs listed in the Stockholm Convention. UN environment programme. [2020-01-09]. （原始內容存檔於2022-02-09）.
^ I.L. Knunyants; G.G. Yakobson. Syntheses of Fluoroorganic Compounds. Springer Science & Business Media. 6 December 2012: 114. ISBN 978-3-642-70207-5.
^ Houben-Weyl Methods of Organic Chemistry Vol. V/3, 4th Edition: Fluorine and Chlorine Compounds. Georg Thieme Verlag. 14 May 2014: 670. ISBN 978-3-13-179994-4.
^ Mayer, Roland; Decker, Daniel; Kniess, Torsten; Lang, Reinhard. Nucleophilic substitution of octachloronaphthalene with organothiolates. Zeitschrift fuer Chemie, 1990. 30 (11): 404-405. ISSN: 0044-2402.
^ Vadim V. Bardin, Svetlana G. Bardina. Fluorine addition to polychlorinated and polybrominated ethenes and arenes using vanadium pentafluoride. Journal of Fluorine Chemistry. 2004-10, 125 (10): 1411–1414 [2021-01-09]. doi:10.1016/j.jfluchem.2004.01.013. （原始內容存檔於2018-06-22）（英語）.
^ Brady, John H.; Redhouse, Alan D.; Wakefield, Basil J. Polyhaloaromatic compounds. Part 47. Synthesis and molecular structure of octabromonaphthalene. Journal of Chemical Research, Synopses, 1982. 6. pp 137.
^ N. R. Conley, J. J. Lagowski. Synthesis of Periodonaphthalene, C 10 I 8 : Permercuration and Subsequent Iododemercuration of Naphthalene in a Triiodide Solution. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry. 2003-01-12, 33 (10): 1741–1745 [2021-01-09]. ISSN 0094-5714. doi:10.1081/SIM-120026544 （英語）.

[GESTIS-1] 1.0 ^1.1 Octachlornaphthalin. GESTIS-Stoffdatenbank. [2020-03-10].

[2] Jeanne Mager Stellman. Encyclopaedia of Occupational Health and Safety. International Labour Organization. 1998: 298. ISBN 978-92-2-109817-1.

[3] All POPs listed in the Stockholm Convention. UN environment programme. [2020-01-09]. （原始內容存檔於2022-02-09）.

[4] I.L. Knunyants; G.G. Yakobson. Syntheses of Fluoroorganic Compounds. Springer Science & Business Media. 6 December 2012: 114. ISBN 978-3-642-70207-5.

[5] Houben-Weyl Methods of Organic Chemistry Vol. V/3, 4th Edition: Fluorine and Chlorine Compounds. Georg Thieme Verlag. 14 May 2014: 670. ISBN 978-3-13-179994-4.

[6] Mayer, Roland; Decker, Daniel; Kniess, Torsten; Lang, Reinhard. Nucleophilic substitution of octachloronaphthalene with organothiolates. Zeitschrift fuer Chemie, 1990. 30 (11): 404-405. ISSN: 0044-2402.

[7] Vadim V. Bardin, Svetlana G. Bardina. Fluorine addition to polychlorinated and polybrominated ethenes and arenes using vanadium pentafluoride. Journal of Fluorine Chemistry. 2004-10, 125 (10): 1411–1414 [2021-01-09]. doi:10.1016/j.jfluchem.2004.01.013. （原始內容存檔於2018-06-22）（英語）.

[8] Brady, John H.; Redhouse, Alan D.; Wakefield, Basil J. Polyhaloaromatic compounds. Part 47. Synthesis and molecular structure of octabromonaphthalene. Journal of Chemical Research, Synopses, 1982. 6. pp 137.

[9] N. R. Conley, J. J. Lagowski. Synthesis of Periodonaphthalene, C 10 I 8 : Permercuration and Subsequent Iododemercuration of Naphthalene in a Triiodide Solution. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry. 2003-01-12, 33 (10): 1741–1745 [2021-01-09]. ISSN 0094-5714. doi:10.1081/SIM-120026544 （英語）.

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