Mercury(II) acetate

Mercury(II) acetate

Names
Other names mercuric acetate mercuriacetate
Identifiers
CAS Number	1600-27-7 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:33211 Y
ChemSpider	14599 Y
ECHA InfoCard	100.014.993
PubChem	15337
UNII	R0G1MCT8Y5 Y
InChI InChI=1S/2C2H4O2.Hg/c2*1-2(3)4;/h2*1H3,(H,3,4);/q;;+2/p-2 Y Key: BRMYZIKAHFEUFJ-UHFFFAOYSA-L Y InChI=1/2C2H4O2.Hg/c2*1-2(3)4;/h2*1H3,(H,3,4);/q;;+2/p-2 Key: BRMYZIKAHFEUFJ-NUQVWONBAS
SMILES [Hg+2].[O-]C(=O)C.[O-]C(=O)C
Properties
Chemical formula	C4H6O4Hg
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)
Solubility in water	25 g/100 mL (10 °C) 100 g/100 mL (100 °C)
Solubility	soluble in alcohol, diethyl ether
Magnetic susceptibility (χ)	−100·10−6 cm3/mol
Hazards
NFPA 704	0 3 0
Lethal dose or concentration (LD, LC):
LD50 (median dose)	40.9 mg/kg (rat, oral) 23.9 mg/kg (mouse, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
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.

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

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:

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:

Mercury(II) acetate is used for oxymercuration reactions.