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What is be the best commercially available source of highly nucleophilic iodide in non-polar solvent? Solvents used are cyclohexane, benzene, chlorobenzene.

I can get ahold of bromide quaternary ammonium salts at best. So I'm looking for equal substituent of Bu4NI. Any ideas?

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  • $\begingroup$ How about cesium iodide? It's soluble in acetone. But no data for less polar solvents. $\endgroup$
    – Mathew Mahindaratne
    Dec 14, 2019 at 17:01
  • $\begingroup$ Benzyltributylammonium iodide is pretty good $\endgroup$
    – Waylander
    Dec 14, 2019 at 20:58
  • $\begingroup$ @waylander "I can get ahold of bromide quaternary ammonium salts at best". Is your suggestion commercially available? $\endgroup$
    – Oscar Lanzi
    Dec 15, 2019 at 13:04
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    $\begingroup$ @OscarLanzi sigmaaldrich.com/catalog/product/aldrich/… $\endgroup$
    – Waylander
    Dec 15, 2019 at 13:46
  • $\begingroup$ A musing, since we had for long a bottle of a solution of 18-crown-6 KCN in the hood only the boss used from time to time, what about the analogue with KI (a bit more than just adding 18-crown-6 + KI + THF, as seen in Acta Cryst 2003, E59, m1184-m1186 (scripts.iucr.org/cgi-bin/paper?S160053680302676X) Aldrich offers some 18C6 with apolar groups attached, eg. dicyclohexane, or dibenzo, etc. $\endgroup$
    – Buttonwood
    Dec 16, 2019 at 21:41

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