Iodine-Aluminum(III) Chloride-Copper(II) Chloride

I2-AlCl3-CuCl2
(I2)

[7553-56-2]  · I2  · Iodine-Aluminum(III) Chloride-Copper(II) Chloride  · (MW 253.80) (AlCl3)

[7446-70-0]  · AlCl3  · Iodine-Aluminum(III) Chloride-Copper(II) Chloride  · (MW 133.33) (CuCl2)

[7447-39-4]  · Cl2Cu  · Iodine-Aluminum(III) Chloride-Copper(II) Chloride  · (MW 134.45)

(iodinating reagent for arenes)

Physical Data: AlCl3: mp 192 °C (2.5 atm); subl. 180 °C. CuCl2: mp 498 °C; d 3.054 g cm-3.

Solubility: AlCl3: sol benzene, CCl4, chloroform; reacts violently with H2O. CuCl2: sol H2O, ethanol, acetone.

Form Supplied in: AlCl3: commercially available; colorless hexagonal plates. CuCl2: yellow to brown, deliquescent microcrystalline powder.

Handling, Storage, and Precautions: AlCl3: moisture sensitive. CuCl2: irritating to skin, mucous membranes; forms dihydrate in moist air. Iodination reactions using this combination of reagents should be performed in a fume hood.

Iodinating Reagents.

Aryl iodides can be prepared by reaction of arene derivatives with Iodine and Antimony(V) Chloride1 and copper salts.2,3 These procedures can be applicable to more reactive substrates such as anisole and xylenes, but not to less reactive substrates such as benzene and halogenated benzene. The reaction of arenes containing halogen with I2 and a mixture of Aluminum Chloride and Copper(II) Chloride gives the corresponding aryl iodides in good yield (eq 1).4 The reaction fails with ethyl benzoate, acetophenone, and o-nitroanisole. The reagents are used in the ratio I2:AlCl3:CuCl2 = 0.5:1:1.


1. Uemura, S.; Onoe, A.; Okano, M. BCJ 1974, 47, 147.
2. Baird, W. C., Jr.; Surridge, J. H. JOC 1970, 35, 3436.
3. Horiuchi, C. A.; Satoh, J. Y. BCJ 1984, 57, 2691.
4. Sugita, T.; Idei, M; Ishibashi, Y.; Takegami, Y. CL 1982, 1481.

C. Akira Horiuchi

Rikkyo (St. Paul's) University, Tokyo, Japan



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