Mercury(II) acetate

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Mercury(II) acetate
Other names
mercuric acetate
1600-27-7 YesY
ChEBI CHEBI:33211 YesY
ChemSpider 14599 YesY
Jmol interactive 3D Image
PubChem 15337
Molar mass 318.678 g/mol
Appearance white-yellow crystals
Odor mild vinegar odor
Density 3.28 g/cm3, solid
Melting point 179 °C (354 °F; 452 K) (decomposes)
25 g/100 mL (10 °C)
100 g/100 mL (100 °C)
Solubility soluble in alcohol, diethyl ether
NFPA 704
Flammability code 0: Will not burn. E.g., water Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Lethal dose or concentration (LD, LC):
40.9 mg/kg (rat, oral)
23.9 mg/kg (mouse, oral)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 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.[2]

Ball-and-stick model of part of the crystal structure of mercury(II) acetate Space-filling model of part of the crystal structure of mercury(II) acetate


Arenes undergo "mercuration" upon treatment with Hg(OAc)2. The one acetate group that remains on mercury can be displaced by chloride:[3]

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:[4]


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

Mercury(II) acetate is used for oxymercuration reactions.


  1. ^ "Mercury (organo) alkyl compounds (as Hg)". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH). 
  2. ^ R. Allmann (1973). Z. Kristallogr., Kristallgeom., Kristallphys., Kristallchem. 138: 366–373.  Missing or empty |title= (help)
  3. ^ Whitmore, F. C.; Hanson, E. R. "o-Chloromercuriphenol" Organic Syntheses, Collected Volume 1, p.161 (1941).
  4. ^ Carter, H. E.; West, H. D. “dl-Serine” Organic Syntheses, Collected Volume 3, p.774 (1955).