Mercury(II) acetate
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| Mercury(II) acetate | |
|---|---|
| Image:Mercury(II) acetate.jpg | |
| Other names | mercuric acetate mercuriacetate |
| Identifiers | |
| CAS number | |
| 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 | 25g/100 mL water (10°C) |
| Hazards | |
| NFPA 704 |
|
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and 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.
Arenes undergo "mercuration" upon treatment with Hg(OAc)2. The one acetate group that remains on mercury can be displaced by chloride:[1]
- C6H5OH + Hg(OAc)2 → C6H4(OH)-2-HgOAc + HOAc
- C6H4(OH)-2-HgOAc + NaCl → C6H4(OH)-2-HgCl + NaOAc
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:[1]
- Hg(OAc)2 + CH2=CHCO2CH3 + CH3OH → CH3OCH2CH(HgOAc)CO2CH3 + HOAc
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:
- (RS)2C=S + H2O + Hg(OAc)2 → (RS)2C=O + HgS + 2 HOAc + "HgO"
References
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de:Quecksilber(II)-acetat it:Acetato mercurico
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
