Mercury(II) acetate

Mercury(II) acetate
Names
Other names
mercuric acetate
mercuriacetate
Identifiers
CAS Number
  • 1600-27-7 checkY
3D model (JSmol)
  • ionic form: Interactive image
  • coordination form: Interactive image
ChEBI
  • CHEBI:33211 checkY
ChemSpider
  • 14599 checkY
ECHA InfoCard 100.014.993 Edit this at Wikidata
EC Number
  • 209-766-2
PubChem CID
  • 15337
RTECS number
  • AI8575000
UNII
  • R0G1MCT8Y5 checkY
UN number 1629
CompTox Dashboard (EPA)
  • DTXSID4042123 Edit this at Wikidata
InChI
  • InChI=1S/2C2H4O2.Hg/c2*1-2(3)4;/h2*1H3,(H,3,4);/q;;+2/p-2 checkY
    Key: BRMYZIKAHFEUFJ-UHFFFAOYSA-L checkY
  • InChI=1/2C2H4O2.Hg/c2*1-2(3)4;/h2*1H3,(H,3,4);/q;;+2/p-2
    Key: BRMYZIKAHFEUFJ-NUQVWONBAS
  • ionic form: [Hg+2].[O-]C(=O)C.[O-]C(=O)C
  • coordination form: O=C(C)O[Hg]OC(C)=O
Properties
Chemical formula
 C4H6O4Hg
Molar mass 318.678 g/mol
Appearance white solid
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
−100·10−6 cm3/mol
Hazards
GHS labelling:
GHS06: ToxicGHS08: Health hazardGHS09: Environmental hazard
Danger
H300, H310, H330, H373, H410
P260, P262, P264, P270, P271, P273, P280, P284, P301+P310, P302+P350, P304+P340, P310, P314, P320, P321, P322, P330, P361, P363, P391, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
4
0
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).
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Infobox references
Chemical compound

Mercury(II) acetate, also known as mercuric acetate is a chemical compound, the mercury(II) salt of acetic acid, 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. It is a white, water-soluble solid, but some samples can appear yellowish with time owing to decomposition.

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]

Synthesis and reactions

Mercury(II) acetate can be produced by reaction of mercuric oxide with acetic acid.[3]

HgO + 2 CH3COOH → Hg(CH3COO)2 + H2O

Inorganic reactions

Mercury(II) acetate in acetic acid solution reacts with H2S to rapidly precipitate the black (β) polymorph of HgS. With gentle heating of the slurry, the black solid converts to the red form.[4] The mineral cinnabar is red HgS. The precipitation of HgS as well as a few other sulfides, using hydrogen sulfide is a step in qualitative inorganic analysis.

Organic chemistry

Electron-rich arenes undergo "mercuration" upon treatment with Hg(OAc)2. This behavior is illustrated with phenol:

C6H5OH + Hg(OAc)2 → C6H4(OH)-2-HgOAc + HOAc

The acetate group (OAc) that remains on mercury can be displaced by chloride:[5]

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 methyl acrylate with mercuric acetate in methanol gives an α-mercuri ester:[6]

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

Exploiting 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.

A famous use of Hg(OAc)2 was in the synthesis of idoxuridine.

Toxicity

Mercuric acetate is a highly toxic compound, due to it being water-soluble and having mercury ions. Symptoms of mercury poisoning include peripheral neuropathy, skin discoloration and dequamation (peeling and/or shedding of the skin).[7] Chronic exposure may cause reduced intelligence and kidney failure.[8]

References

  1. ^ "Mercury (organo) alkyl compounds (as Hg)". Immediately Dangerous to Life or 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. S2CID 96160619.
  3. ^ F. Wagenknecht; R. Juza (1963). "Mercury(II) Acetate". In G. Brauer (ed.). Handbook of Preparative Inorganic Chemistry, 2nd Ed. Vol. 2. NY, NY: Academic Press. p. 1120.
  4. ^ Newell, Lyman C.; Maxson, R. N.; Filson, M. H. (1939). "Red Mercuric Sulfide". Inorganic Syntheses. Vol. 1. pp. 19–20. doi:10.1002/9780470132326.ch7. ISBN 9780470132326.
  5. ^ Whitmore, F. C.; Hanson, E. R. (1925). "o-Chloromercuriphenol". Organic Syntheses. 4: 13. doi:10.15227/orgsyn.004.0013.
  6. ^ Carter, Herbert E.; West, Harold D. (1940). "DL-Serine". Organic Syntheses. 20: 81. doi:10.15227/orgsyn.020.0081.
  7. ^ Bernhoft, Robin A. (2012). "Mercury Toxicity and Treatment: A Review of the Literature". Journal of Environmental and Public Health. 2012: 1–10. doi:10.1155/2012/460508. ISSN 1687-9805. PMC 3253456. PMID 22235210.
  8. ^ Bose-O'Reilly, Stephan; McCarty, Kathleen M.; Steckling, Nadine; Lettmeier, Beate (September 2010). "Mercury Exposure and Children's Health". Current Problems in Pediatric and Adolescent Health Care. 40 (8): 186–215. doi:10.1016/j.cppeds.2010.07.002. PMC 3096006. PMID 20816346.
  • v
  • t
  • e
Mercury(I)
  • HgH
  • Hg2H2
  • Hg2Br2
  • Hg2Cl2
  • Hg2F2
  • Hg2I2
  • Hg2(NO3)2
  • Hg2O
  • Hg2CO3
  • Hg2SO4
  • Hg2S (hypothetical)
Mercury(II)
  • HgH2
  • HgNH2Cl
  • HgSe
  • HgS
  • HgTe
  • Hg(O2CCH3)2
  • HgBr2
  • HgCl2
  • Hg(CN)2
  • HgF2
  • Hg(OH)2
  • HgI2
  • Hg(NO3)2
  • HgO
  • HgSO4
  • Hg(SCN)2
  • Hg(CNO)2
  • Hg3N2
  • Hg(Si(CH3)3)2
  • K2HgI4
Organomercury
compounds
  • Hg(CH3)2
  • Hg(C2H5)2
  • Hg(C6H5)2
  • HgC6H5CH3CO2
  • HgC6H5OB(OH)2
  • HgC6H5NO3
  • HgC6H5CCl3
  • HgClC6H4CO2H
  • HgOHCH2CHOCH3CH2(NHCO)
  • C
    36    H
    70    HgO
    4
  • HgOHCH2CHOCH3CH2NHCOC6H4OCH2CO2H
  • Na2HgOHC6HOBrC6H2OBrOCHC6H4CO2
  • HgOC6H2CH3NO2
  • NaHgC2H5SC6H4CO2
Mercury(IV)
  • HgF4 (hypothetical)
Amalgams
Mercury cations
  • Hg2+
  • Hg22+
  • Hg32+
  • Hg42+
  • Hg34+
  • HgCH3+
  • HgC2H5+
  • HgC6H5+
  • v
  • t
  • e
Acetyl halides and salts of the acetate ion
AcOH He
LiOAc Be(OAc)2
Be4O(OAc)6 		B(OAc)3
B2O(OAc)4 		AcOAc
ROAc 		NH4OAc AcOOH FAc
FOAc 		Ne
NaOAc
NaH(OAc)2 		Mg(OAc)2 Al(OAc)3
ALSOL
Al(OAc)2OH
Al(OH)2OAc
Al2SO4(OAc)4 		Si P S ClAc
ClOAc 		Ar
KOAc Ca(OAc)2 Sc(OAc)3 Ti(OAc)4 VO(OAc)3 Cr(OAc)2
Cr(OAc)3 		Mn(OAc)2
Mn(OAc)3 		Fe(OAc)2
Fe(OAc)3 		Co(OAc)2 Ni(OAc)2 CuOAc
Cu(OAc)2 		Zn(OAc)2 Ga(OAc)3 Ge As(OAc)3 Se BrAc
BrOAc 		Kr
RbOAc Sr(OAc)2 Y(OAc)3 Zr(OAc)4 Nb Mo(OAc)2 Tc Ru2(OAc)4Cl
Ru(OAc)3 		Rh2(OAc)4 Pd(OAc)2 AgOAc Cd(OAc)2 In(OAc)3 Sn(OAc)2
Sn(OAc)4 		Sb(OAc)3 Te IAc
IOAc
I(OAc)3 		Xe
CsOAc Ba(OAc)2 * Lu(OAc)3 Hf Ta W Re Os Ir Pt(OAc)2 Au(OAc)3 Hg2(OAc)2
Hg(OAc)2 		TlOAc
Tl(OAc)3 		Pb(OAc)2
Pb(OAc)4 		Bi(OAc)3 Po At Rn
Fr Ra ** Lr Rf Db Sg Bh Hs Mt Ds Rg Cn Nh Fl Mc Lv Ts Og
 
* La(OAc)3 Ce(OAc)3 Pr(OAc)3 Nd(OAc)3 Pm Sm(OAc)3 Eu(OAc)3 Gd(OAc)3 Tb(OAc)3 Dy(OAc)3 Ho(OAc)3 Er(OAc)3 Tm(OAc)3 Yb(OAc)3
** Ac(OAc)3 Th(OAc)4 Pa UO2(OAc)2 Np Pu Am Cm Bk Cf Es Fm Md No