Description
Mercury (II) acetate is the chemical compound with the formula Hg(O
2CCH
3)
2. Commonly abbreviated Hg (OAc)
2, this compound is employed as a reagent to generate organomercury compounds from unsaturated organic precursors.
Chemical Properties
Mercuric acetate is a white crystalline solid
with a mild vinegar-like odor.
Chemical Properties
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.
Physical properties
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.
Uses
Chiefly for mercuration of organic compounds; for the absorption of ethylene.
Uses
Used in determination of nitrate in chromium compounds
Uses
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.
Reactions
Arenes undergo "mercuration" upon treatment with Hg(OAc)
2. The one acetate group that remains on mercury can be displaced by chloride :
C
6H
5OH + Hg(OAc)
2 → C
6H
4(OH)-2-HgOAc + HOAc
C
6H
4(OH)-2-HgOAc + NaCl → C
6H
4(OH)-2-HgCl + NaOAc
The Hg
2+ 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 + CH
2 = CHCO
2CH
3 + CH
3OH → CH
3OCH
2CH(HgOAc)CO
2CH
3+ 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 + H
2O + Hg(OAc)
2 → (RS)
2C=O + HgS + 2 HOAc
Mercury (II) acetate is used for oxymercuration reactions.
General Description
White crystalline solid with an odor of vinegar. Sensitive to light. Density 3.25 g / cm3. Toxic by inhalation (dust, etc.) and by ingestion.
Air & Water Reactions
Water soluble. Decomposed by water to form a yellow insoluble product.
Reactivity Profile
MERCURIC ACETATE is incompatible with acetylene, ammonia, chlorine dioxide, azides, calcium (amalgam formation), sodium carbide, lithium, rubidium, and copper .
Hazard
Toxic by ingestion, inhalation, and skin
absorption; strong irritant.
Health Hazard
MERCURIC ACETATE may cause death by hypovolemic shock or kidney failure. Chronic exposure may lead to kidney failure.
Fire Hazard
When heated to decomposition, MERCURIC ACETATE emits toxic fumes of mercury. Avoid light.
reaction suitability
reagent type: catalyst
core: mercury
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.
Potential Exposure
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.
First aid
If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Speed in removing material from skin is of extreme importance. Shampoo hair promptly if contaminated. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. If victim is conscious, administer water or milk. Do not induce vomiting. Medical observation is recommended for 2448 h after breathing overexposure, as pulmonary edema may be delayed. As first aid for pulmonary edema, a doctor or authorized paramedic may consider administering a corticosteroid spray. Antidotes and special procedures for medical personnel: The drug NAP (n-acetyl penicillamine) has been used to treat mercury poisoning, with mixed success. Note to physician: For severe poisoning BAL [British AntiLewisite, dimercaprol, dithiopropanol (C3H8OS2)] has been used to treat toxic symptoms of certain heavy metals poisoning including mercury. Although BAL is reported to have a large margin of safety, caution must be exercised, because toxic effects may be caused by excessive dosage. Most can be prevented by premedication with 1-ephedrine sulfate (CAS: 134-72-5).
storage
Color Code—Blue: Health Hazard/Poison: Store in a secure poison location. Prior to working with this chemical you should be trained on its proper handling and storage. Store in tightly closed containers in a cool, wellventilated area away from oxidizers (such as perchlorates, peroxides, permanganates, chlorates and nitrates), light, heat, and acids.
Shipping
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.]
Incompatibilities
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.
