Organomercury chemistry

Many organomercury compounds are highly toxic, but some are used in medicine, e.g., merbromin ("Mercurochrome") and the vaccine preservative thiomersal.

Merbromin and phenylmercuric borate are used as topical antiseptics, while thimerosal is safely used as a preservative for vaccines and antitoxins.

The one acetate group that remains on the mercury atom can be displaced by chloride:[8] The first such reaction, including a mercuration of benzene itself, was first reported by Otto Dimroth in 1898.

Diethylmercury results from the reaction of mercury chloride with two equivalents of ethylmagnesium bromide, a conversion that would typically be conducted in diethyl ether solution.

Similarly, diphenylmercury (melting point 121–123 °C) can be prepared by reaction of mercury chloride and phenylmagnesium bromide.

[15] 4-Chloromercuritoluene is obtained by the chloromercuration of sodium toluenesulfinite:[16] Organomercury compounds are versatile synthetic intermediates due to the well-controlled conditions under which Hg-C bonds undergo cleave.

[17] This compound on heating releases dichlorocarbene: Cross coupling of organomercurials with organic halides is catalyzed by palladium.

Carbonylation of lactones has been shown to employ Hg(II) reagents under palladium catalyzed conditions.

Acetaldehyde is produced by hydration of acetylene:[21] The Hg-containing waste stream of the Chisso process led to the environmental catastrophe causing Minamata disease.

In general oxymercuration reactions of alkenes and alkynes using mercuric compounds proceed via organomercury intermediates.

[23] This mode of action makes them useful for affinity chromatography to separate thiol-containing compounds from complex mixtures.