while iodomethane is formed in situ. Iodides are generally expensive relative to the more common chlorides and bromides, though iodomethane is reasonably affordable; on a commercial scale, the more toxic dimethyl sulfate is preferred, since it is cheap and has a higher boiling point. The iodide leaving group in iodomethane may cause unwanted side reactions. Finally, being highly reactive, iodomethane is more dangerous for laboratory workers than related chlorides and bromides. For example, it can be used for the methylation of carboxylic acids or phenols: In these examples, the base (K2CO3 or Li2CO3) removes the acidic proton to form the carboxylate or phenoxide anion, which serves as the nucleophile in the SN2 substitution. Iodide is a "soft" anion which means that methylation with MeI tends to occur at the "softer" end of an ambidentate nucleophile. For example, reaction with thiocyanate ion favours attack at sulfur rather than "hard" nitrogen, leading mainly to methyl thiocyanate (CH3SCN) rather than methyl isothiocyanate CH3NCS. This behavior is relevant to the methylation of stabilized enolates such as those derived from 1,3-dicarbonyl compounds. Methylation of these and related enolates can occur on the harder oxygen atom or the (usually desired) carbon atom. With iodomethane, C-alkylation nearly always predominates. Other reactions In the Monsanto process and the Cativa process, MeI forms in situ from the reaction of methanol and hydrogen iodide. The CH3I then reacts with carbon monoxide in the presence of a rhodium or iridium complex to form acetyl iodide, the precursor to acetic acid after hydrolysis. The Cativa process is usually preferred because less water is required to use and there are less byproducts. MeI is used to prepare the Grignard reagent, methylmagnesium iodide ("MeMgI"), a common source of "Me−". The use of MeMgI has been somewhat superseded by the commercially available methyllithium. MeI can also be used to prepare dimethylmercury, by reacting 2 moles of MeI with a 2/1-molar sodium amalgam (2 moles of sodium, 1 mol of mercury). Iodomethane and other organic iodine compounds do form under the conditions of a serious nuclear accident, after both Chernobyl and Fukushima, Iodine-131 was detected in organic iodine compounds in Europe and Japan respectively. Use as a pesticide Iodomethane had also been proposed for use as a fungicide, herbicide, insecticide, nematicide, and as a soil disinfectant, replacing methyl bromide (also known as bromomethane) (banned under the Montreal Protocol). Manufactured by Arysta LifeScience and sold under the