| Mercury(II) acetate | |
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Other names
mercuric acetate |
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| Identifiers | |
| CAS number | 1600-27-7 |
| ChemSpider | 14599 |
| UNII | R0G1MCT8Y5 |
| ChEBI | CHEBI:33211 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C4H6O4Hg |
| Molar mass | 318.70 g/mol |
| Appearance | white crystals |
| Density | 3.27 g/cm³, solid |
| Melting point |
179 °C (decomposes) |
| Solubility in water | 25 g/100 mL (10 °C) |
| Solubility | soluble in alcohol |
| Hazards | |
| NFPA 704 |
0
3
0
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| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Mercury(II) acetate is the chemical compound with the formula Hg(O2CCH3)2. Commonly abbreviated Hg(OAc)2, this compound is employed as a reagent to generate organomercury compounds from unsaturated organic precursors.
Mercury(II) acetate is a crystalline solid consisting of isolated Hg(OAc)2 molecules with Hg-O distances of 2.07 Å. Three long, weak intermolecular Hg···O bonds of about 2.75 Å are also present, resulting in a slightly distorted square pyramidal coordination geometry at Hg.[1]
Arenes undergo "mercuration" upon treatment with Hg(OAc)2. The one acetate group that remains on mercury can be displaced by chloride:[2]
The Hg2+ center binds to alkenes, inducing the addition of hydroxide and alkoxide. For example, treatment of methylacrylate with mercuric acetate in methanol gives an α-mercuri ester:[3]
Mercury(II) has a high affinity for sulfur ligands. Hg(OAc)2 can be used as a reagent to remove the acetamidomethyl protecting group, which is used to "protect" thiol groups in organic synthesis. Similarly Hg(OAc)2 is a standard reagent to convert thiocarbonate esters into dithiocarbonates:
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