Mercury(II) acetate

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
[[File:Mercury(II)- mercuric acid acetate-from-xtal-1973-3D-balls-A.png|220px]]
Names
Other names
mercuric acetate
mercuriacetate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.014.993
EC Number
  • 209-766-2
RTECS number
  • AI8575000
UNII
UN number 1629
Properties
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)
25 g/100 mL (10 °C)
100 g/100 mL (100 °C)
Solubility soluble in alcohol, diethyl ether
−100·10−6 cm3/mol
Hazards
GHS pictograms
GHS Signal word Danger
H300, H310, H330, H373, H400, H410
P260, P262, P264, P270, P271, P273, P280, P284, P301+310, P302+350, P304+340, P310, P314, P320, P321, P322, P330, P361, P363, P391, P403+233, P405, P501
NFPA 704 (fire diamond)
Flammability code 0: Will not burn. E.g. waterHealth code 4: Very short exposure could cause death or major residual injury. E.g. VX gasReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
4
0
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).
N verify (what is YN ?)
Infobox references

Structure

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]

Reactions

Arenes undergo "mercuration" upon treatment with Hg(OAc)2. The one acetate group (OAc) 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]

Hg(OAc)2 + CH2=CHCO2CH3 + CH3OH → CH3OCH2CH(HgOAc)CO2CH3 + HOAc

Exploitting the high affinity of mercury(II) for sulfur ligands, Hg(OAc)2 can be used as a reagent to deprotect thiol groups in organic synthesis. Similarly Hg(OAc)2 has been used 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.

References
  1. "Mercury (organo) alkyl compounds (as Hg)". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  2. Allmann, R. (1973). "Die Struktur des Quecksilber(II)-acetats". Zeitschrift für Kristallographie - Crystalline Materials. 138 (1–6): 366–373. doi:10.1524/zkri.1973.138.jg.366.
  3. Whitmore, F. C.; Hanson, E. R. (1925). "o-chloromercuriphenol". Organic Syntheses. 4: 13. doi:10.15227/orgsyn.004.0013.
  4. "Dl-SERINE". Organic Syntheses. 20: 81. 1940. doi:10.15227/orgsyn.020.0081.
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