Mercury(II) acetate

Mercury(II) acetate
	[[File:Mercury(II)- mercuric acid acetate-from-xtal-1973-3D-balls-A.png\|220px]]
Names
	Other names mercuric acetate; mercuriacetate
Identifiers
CAS Number	1600-27-7 ;
3D model (JSmol)	ionic form: Interactive image; coordination form: Interactive image;
ChEBI	CHEBI:33211 ;
ChemSpider	14599 ;
ECHA InfoCard	100.014.993
EC Number	209-766-2;
PubChem CID	15337;
RTECS number	AI8575000;
UNII	R0G1MCT8Y5 ;
UN number	1629
CompTox Dashboard (EPA)	DTXSID4042123 ;
	InChI InChI=1S/2C2H4O2.Hg/c21-2(3)4;/h21H3,(H,3,4);/q;;+2/p-2 Key: BRMYZIKAHFEUFJ-UHFFFAOYSA-L ; InChI=1/2C2H4O2.Hg/c21-2(3)4;/h21H3,(H,3,4);/q;;+2/p-2 Key: BRMYZIKAHFEUFJ-NUQVWONBAS;
	SMILES 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-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
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H300, H310, H330, H373, H400, H410
GHS precautionary statements	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)	0 4 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).

Mercury(II) acetate is the chemical compound with the formula Hg(O₂ CCH₃)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]

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

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

^ "Mercury (organo) alkyl compounds (as Hg)". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^ 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.
^ Whitmore, F. C.; Hanson, E. R. (1925). "o-chloromercuriphenol". Organic Syntheses. 4: 13. doi:10.15227/orgsyn.004.0013.
^ "Dl-SERINE". Organic Syntheses. 20: 81. 1940. doi:10.15227/orgsyn.020.0081.

Acetyl halides and salts of the acetate ion
AcOH																		He
LiOAc	Be(OAc)₂ BeAcOH												B(OAc)₃	AcOAc ROAc	NH₄OAc	AcOOH	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 Cr(OAc)₃	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	*	Lu(OAc)₃	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	**	Lr	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
		**	Ac	Th	Pa	UO₂(OAc)₂	Np	Pu	Am	Cm	Bk	Cf	Es	Fm	Md	No

[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.

[1]

[2]

[3]

[4]

Names

[[File:Mercury(II)- mercuric acid acetate-from-xtal-1973-3D-balls-A.png\|220px]]

Other names mercuric acetate mercuriacetate
Identifiers
CAS Number	1600-27-7
3D model (JSmol)	ionic form: Interactive image coordination form: Interactive image
ChEBI	CHEBI:33211
ChemSpider	14599
ECHA InfoCard	100.014.993
EC Number	209-766-2
PubChem CID	15337
RTECS number	AI8575000
UNII	R0G1MCT8Y5
UN number	1629
CompTox Dashboard (EPA)	DTXSID4042123
InChI InChI=1S/2C2H4O2.Hg/c21-2(3)4;/h21H3,(H,3,4);/q;;+2/p-2 Key: BRMYZIKAHFEUFJ-UHFFFAOYSA-L InChI=1/2C2H4O2.Hg/c21-2(3)4;/h21H3,(H,3,4);/q;;+2/p-2 Key: BRMYZIKAHFEUFJ-NUQVWONBAS
SMILES 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-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
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H300, H310, H330, H373, H400, H410
GHS precautionary statements	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)	0 4 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).