八氯萘

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八氯萘
File:Octachloornaftaleen t.png
识别
CAS号 2234-13-1  checkY
SMILES
 
  • Clc1c(Cl)c(Cl)c(Cl)c2c1c(Cl)c(Cl)c(Cl)c2Cl
性质
化学式 C10Cl8
摩尔质量 403.73 g·mol−1
外观 黄色固体
密度 2.0 g·cm−3[1]
熔点 197.5—198 °C(470.6—471.1 K)
沸点 440 °C(713 K)
溶解性 难溶
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

八氯萘是一种有机化合物,化学式为C10Cl8。它是难溶于水的黄色固体[1][2],于2015年作为多氯萘列入斯德哥尔摩公约附录A和附录C中。[3]它可由磺酰氯中在氯化铁的存在下和氯气反应制得[4];或由萘和氯气五氯化锑的存在下于150~210 °C反应得到。[5]它和乙硫醇钠DMF中反应,可以得到八(乙硫基)萘。[6]它在45~50 °C可以被五氟化钒氧化,得到C10Cl8F8VF4[7]

参见[编辑]

  • 八氟萘,C10F8
  • 八溴萘,C10Br8,CAS号22245-33-6,汞化后和KBr3反应得到[8]
  • 八碘萘,C10I8,CAS号701977-35-7,汞化后和KI3反应得到[9]

参考文献[编辑]

  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]. (原始内容存档于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. (原始内容存档于2018-06-22) (English). 
  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 (English).