1,2-二碘乙烷

化合物

1,2-二碘乙烷是一种有机化合物,化学式为C2H4I2

1,2-二碘乙烷
Skeletal formula of 1,2-diiodoethane
Stick and Balls model of 1,2-diiodoethane
Tube model of 1,2-diiodoethane
Space Filling model of 1,2-diiodoethane
IUPAC名
1,2-diiodoethane
别名 ethylene iodide
识别
CAS号 624-73-7
PubChem 12224
ChemSpider 11723
SMILES
 
  • C(CI)I
InChI
 
  • 1/C2H4I2/c3-1-2-4/h1-2H2
InChIKey GBBZLMLLFVFKJM-UHFFFAOYAR
性质
化学式 C2H4I2
摩尔质量 281.86 g·mol−1
密度 2.132 g·cm−3(10 °C)[1]
熔点 82 °C(355 K)[1]
沸点 200 °C(473 K)[2]
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

制备及性质

编辑

1,2-二碘乙烷可由乙烯单质反应得到:[3]

C2H4 + I2 ⇌ C2H4I2

1,2-二氯乙烷碘化钠四丁基碘化铵的催化下于DMF中加热,发生卤素交换反应,得到1,2-二碘乙烷。[4]乙二醇氢碘酸加热反应,也可得到该化合物。[5]

1,2-二碘乙烷在有机合成中主要用于二碘化钐二碘化镱的制备:[6]

Sm + ICH2CH2I → SmI2 + H2C=CH2 (惰性气氛、THF作为溶剂)

参考文献

编辑
  1. ^ 1.0 1.1 Jaeger, F. M. Crystallography of the Aliphatic Compounds. Zeitschrift fuer Kristallographie und Mineralogie, 1909. 45: 539-547. ISSN: 0372-9176.
  2. ^ Gordon G. Cash, Suzanne Hartigan, Jay Tunkel. Normal boiling points of haloalkanes from electrotopological state indices. Toxicological & Environmental Chemistry. 2008-11, 90 (6): 1073–1089 [2020-05-29]. ISSN 0277-2248. doi:10.1080/02772240701862116 (英语). 
  3. ^ Cutherbertson, G.R.; Kistiakowsky, G.B. The thermal equilibrium between ethylene iodide, ethylene and iodine. J. Chem. Phys. 1935, 3 (10): 631–634. Bibcode:1935JChPh...3..631C. doi:10.1063/1.1749566. 
  4. ^ Herlekar, Omkar Pravin; Durve, Ketakee Sanjay; Chaudhari, Nikhil Vitthal. Process for terminal dihaloalkane. 2012. IN 2012MU01684 A.
  5. ^ Doya, Masaharu; Hoshino, Yuki. Preparation of iodine compounds by alcohol iodination using hydriodic acid while removing generated water. 2010. JP 2010159223 A.
  6. ^ Girard, P.; Namy, J. L.; Kagan, H. B. Divalent lanthanide derivatives in organic synthesis. 1. Mild preparation of samarium iodide and ytterbium iodide and their use as reducing or coupling agents. Journal of the American Chemical Society. 1980, 102 (8): 2693–2698. doi:10.1021/ja00528a029.