Dimethylmercury a highly toxic organic mercury compound

Dimethylmercury ((CH3)2Hg), also known as dimethylmercury, is a highly toxic organic mercury compound. Dimethylmercury is a highly volatile, reactive, flammable, colorless liquid that is one of the most potent neurotoxins known. Amounts less than 0.1 ml can cause severe mercury poisoning, leading to death, and can easily Absorbed through the skin. Dimethylmercury is able to penetrate many materials, including plastics and rubber compounds. It has been described as having a slightly sweet smell, although those who reported its smell were exposed to harmful amounts
Synthesis, Structure and Reactions
This compound is one of the first reported organometallic compounds, reflecting its considerable stability. The compound was first prepared by George Buckton in 1857 by the reaction of methylmercuric iodide with potassium cyanide
Reactivity and Physical Properties
An unusual feature of this compound is its low reactivity towards proton sources, being stable in water and reacting with inorganic acids at significant rates only at elevated temperatures,[5][6] whereas the corresponding organocadmium and organozinc The compound (and most metal alkyls in general) hydrolyzes rapidly. This difference reflects the high electronegativity of Hg (Pauling EN = 2.00) and the low affinity of Hg(II) for oxygen ligands. This compound undergoes a redistribution reaction with mercuric chloride to form methylmercury chloride
Due to the risks involved, dimethylmercury is currently rarely used. Like many methylorganometallics, it is a methylating agent that donates methyl groups to organic molecules; however, less toxic nucleophiles such as dimethylzinc, trimethylaluminum, and lattice The development of Regent's reagents (organic magnesium halides) essentially made this compound obsolete in organic chemistry. Reactions involving the binding of methylmercury cations to target molecules to form effective fungicides have also been investigated, but the bioaccumulation and eventual toxicity of methylmercury have largely led to their abandonment in favor of the less toxic acetylene Mercury and diethylmercury compounds, which perform similar functions without bioaccumulating hazards.

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