Tert-Butyl iodide

tert-Butyl iodide is an organoiodine compound with the formula Me₃CI. The molecule features a tert-butyl group attached to a iodide substituent.
This chemical is used as a precursor for the tert-butyl radical in various organic chemical reactions. It can also serve as an electrophile in many types of reactions. Examples include for conversion of amino acids to their tert-butyl esters under mild conditions, Heck reactions and electrophilic [aromatic substitution]s. In combination with DMSO and an additional oxidizing agent such as iodine, it can convert aryl-methyl groups to the corresponding aryl aldehydes. The reaction is postulated to proceed via generation of an intermediate alkoxysulfonium species.