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« MCPBA (Warning: oxidant may be explodey) | Main | Inulin (The Jerusalem artichoke and the blustery day) »

Chloranil (Annoying oxidants)

Category: Synthesis
Posted on: April 17, 2007 7:40 PM, by Molecule of the Day

Sorry for the short updates this week! Chloranil is an oxidizing agent. Part of its usefulness comes from its solubility in organic solvent, which you don't see with things like permanganate or H2O2.

InChI=1/C6Cl4O2/c7-1-2(8)6(12)4(10)3(9)5(1)11

The idea with chloranil is that it's a stronger p-quinone. It is a pain to use. It's not very soluble, and I've never had very much luck with it.. On the other hand, it has a beautiful yellow color.

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Katz at Columbia University efficently made and homologated helicenes and heterohelicenes (pyrroles, thiophenes, furans) using quinone as reactant, oxidant, and solvent all together. Those must have been jolly workups.

Chlorine isn't Green. OK, so it is, but it isn't. The second battle of Ypres, 1915 - 5700 canisters containing 168 tons of chlorine gas. And Seveso, Italy. Every salt shaker is suspect. And the oceans, too - unknown hazards!

Posted by: Uncle Al | April 18, 2007 1:42 PM

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