Chemical Properties
Off-White/Brown Crystalline Powder
Uses
Oxidizing agent for use in liquid ammonia: Kline, Kershner, Inorg. Chem. 5, 932 (1966).
General Description
White crystalline plates. Light sensitive. Density 3.26 g /cm3.
Reactivity Profile
SILVER ACETATE(563-63-3) is freely soluble in dilute nitric acid [Merck]. Can serve as an oxidizing agent.
Air & Water Reactions
Slightly soluble in water.
Health Hazard
Inhalation of dust irritates nose and throat. Contact with eyes or skin causes irritation. If continued for a long period, ingestion or inhalation of silver compounds can cause permanent discoloration of skin (argyria).
Reactions
3 – 1 - Carbonylation
Silver acetate, when combined with carbon monoxide (CO), can induce the carbonylation of primary and secondary amines. Other silver salts can be used but the acetate gives the best yield.
2 R2NH + 2 AgOAc + CO → [R2N]2CO + 2 HOAc + 2 Ag
3 – 2 - Hydrogenation
Silver acetate in a solution of pyridine absorbs hydrogen and is reduced to metallic silver.
3 – 3 - Direct ortho - arylation
Silver acetate is a useful reagent for direct ortho-arylation (to install two adjacent substituents on an aromatic ring) for of benzylamines and N-methylbenzylamines. The reaction is palladiumcatalized and requires a slight excess of silver acetate.This reaction is shorter than previous ortho-arylation methods.
Brand name
Smokerette;Tabmint.
World Health Organization (WHO)
Silver acetate has been used as a disinfectant and as an antismoking
aid. It was refused registration in Cyprus on the grounds that prolonged use of silver salts can cause permanent argyria and that no well-controlled trials
have been performed to establish the safety and efficacy of the preparation. It
remains registered as an aid to stopping smoking in Canada and the United States.
Purification Methods
Shake it with acetic acid for three days, and the process is repeated with fresh acid. The solid is then dried in a vacuum oven at 40o for 48hours. It has also been recrystallised from water containing a trace of acetic acid, and dried in air. Store it in the dark. [Beilstein 2 IV 112.]
Safety
The LD50 of silver acetate in mice is 36.7 mg/kg. Low doses of silver acetate in mice produced hyper-excitability, ataxia, central nervous system depression, labored breathing, and even death. The U.S. FDA recommends that silver acetate intake be limited to 756 mg over a short period of time; excessive intake may cause argyria.
Synthesis
The silver acetate salt can be synthesized by the reaction of acetic acid and silver carbonate at 45 – 60 °C. After allowing cooling to room temperature, the solid product precipitates.
2 CH3CO2H + Ag2CO3 → 2 AgO2CCH3 + H2O + CO2
It can also be precipitated from concentrated aqueous solutions of silver nitrate by treatment with a solution of sodium acetate.
The structure of silver acetate consists of 8-membered Ag2O4C2 rings formed by a pair of acetate ligands bridging a pair of silver centres.
