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개요

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.

화학적 성질

Mercuric acetate, Hg(C2H3O2)2 , is a toxic, light-sensitive white powder, soluble in water,alcohol,and acetic acid. On exposure to heat, mercuric acetate produces toxic fumes of mercury/mercuric oxide. Mercuric acetate is incompatible with chromic acid, chromic anhydride, nitric acid, perchloric acid, permanganates, sodium peroxide, potassium hydroxide, hydrogen peroxides, acid anhydrides, and strong oxidising agents.

물리적 성질

Mercury(II) acetate is a crystalline solid consisting of isolated Hg(OAc)₂ molecules with Hg-O distances of 2.07 ?. Three long, weak intermolecular Hg···O bonds of about 2.75 ? are also present,resulting in a slightly distorted square pyramidal coordination geometry at Hg.

용도

Mercuric acetate is used as an oxidizing agent in organic synthesis. It is used in oxymercuration of double bonds. Mercuric acetate is used in non-aqueous titration. It is employed in the manufacture of phenyl mercury compounds which have pharmaceutical applications. It removes the acetamidomethyl protecting group from protected thiol, and converts thiocarbonate esters into dithiocarbonates. It promotes the addition of hydroxide and alkoxide across carbon-carbon double bonds.

화학 반응

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

일반 설명

White crystalline solid with an odor of vinegar. Sensitive to light. Density 3.25 g / cm3. Toxic by inhalation (dust, etc.) and by ingestion.

공기와 물의 반응

Water soluble. Decomposed by water to form a yellow insoluble product.

반응 프로필

MERCURIC ACETATE is incompatible with acetylene, ammonia, chlorine dioxide, azides, calcium (amalgam formation), sodium carbide, lithium, rubidium, and copper .

위험도

Toxic by ingestion, inhalation, and skin absorption; strong irritant.

건강위험

MERCURIC ACETATE may cause death by hypovolemic shock or kidney failure. Chronic exposure may lead to kidney failure.

화재위험

When heated to decomposition, MERCURIC ACETATE emits toxic fumes of mercury. Avoid light.

Safety Profile

Poison by ingestion, intravenous, intraperitoneal, and subcutaneous routes. Moderately toxic by skin contact. An experimental teratogen. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of Hg. See also MERCURY COMPOUNDS.

잠재적 노출

Mercuric acetate is used chiefly for mercuration of organic compounds; for the absorption ofethylene; as a chemical intermediate for phenylmercuric acetate; a mildewcide; and other organomercury compounds. It is used as a catalyst in organic synthesis; and in the manufacture of pharmaceuticals.

운송 방법

UN1629 Mercury acetate, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Purification Methods

Recrystallise it from glacial acetic acid. POISONOUS. [Beilstein 2 IV 114.]

비 호환성

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Light and heat can cause decomposition.

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