Mercury(II) acetate

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Mercury(II) acetate
Image:Mercury(II) acetate.jpg
Other names	mercuric acetate mercuriacetate
Identifiers
CAS number	[1600-27-7]
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	3
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:^[2]

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"

[edit] References

1. ^ Whitmore, F. C.; Hanson, E. R. "o-Chloromercuriphenol" Organic Syntheses, Collected Volume 1, p.161 (1941).http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV1P0161
2. ^ Carter, H. E.; West, H. D. “dl-Serine” Organic Syntheses, Collected Volume 3, p.774 (1955). http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV3P0774