Mercury(II) acetate

Mercury(II) acetate

Names
Other names mercuric acetate mercuriacetate
Identifiers
CAS Number	1600-27-7
3D model (Jmol)	Interactive image
ChEBI	CHEBI:33211
ChemSpider	14599
ECHA InfoCard	100.014.993
PubChem	15337
UNII	R0G1MCT8Y5
InChI InChI=1S/2C2H4O2.Hg/c2*1-2(3)4;/h2*1H3,(H,3,4);/q;;+2/p-2 Key: BRMYZIKAHFEUFJ-UHFFFAOYSA-L 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/cm^3, 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
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)[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.

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 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

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.

References

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).http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV1P0161
4. 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

Salts and the ester of the acetate ion
AcOH																	He
LiOAc	Be(OAc)2 BeAcOH											B(OAc)3	ROAc	NH4OAc	AcOAc	FAc	Ne
NaOAc	Mg(OAc)2											Al(OAc)3 ALSOL Al(OAc)2OH Al2SO4(OAc)4	Si	P	S	ClAc	Ar
KOAc	Ca(OAc)2	Sc(OAc)3	Ti(OAc)4	VO(OAc)3	Cr(OAc)2	Mn(OAc)2 Mn(OAc)3	Fe(OAc)2 Fe(OAc)3	Co(OAc)2, Co(OAc)3	Ni(OAc)2	Cu(OAc)2	Zn(OAc)2	Ga(OAc)3	Ge	As(OAc)3	Se	BrAc	Kr
RbOAc	Sr(OAc)2	Y(OAc)3	Zr(OAc)4	Nb	Mo(OAc)2	Tc	Ru(OAc)2 Ru(OAc)3 Ru(OAc)4	Rh2(OAc)4	Pd(OAc)2	AgOAc	Cd(OAc)2	In	Sn(OAc)2 Sn(OAc)4	Sb(OAc)3	Te	IAc	Xe
CsOAc	Ba(OAc)2		Hf	Ta	W	Re	Os	Ir	Pt(OAc)2	Au	Hg2(OAc)2, Hg(OAc)2	TlOAc Tl(OAc)3	Pb(OAc)2 Pb(OAc)4	Bi(OAc)3	Po	At	Rn
Fr	Ra		Rf	Db	Sg	Bh	Hs	Mt	Ds	Rg	Cn	Nh	Fl	Mc	Lv	Ts	Og
		↓
		La(OAc)3	Ce(OAc)x	Pr	Nd	Pm	Sm(OAc)3	Eu(OAc)3	Gd(OAc)3	Tb	Dy(OAc)3	Ho(OAc)3	Er	Tm	Yb(OAc)3	Lu(OAc)3
		Ac	Th	Pa	UO2(OAc)2	Np	Pu	Am	Cm	Bk	Cf	Es	Fm	Md	No	Lr