Silver acetate

Silver acetate

Names
Other names Acetic acid, silver (1+) salt Silver ethanoate
Identifiers
CAS Number	563-63-3 Y
3D model (Jmol)	Interactive image
ChemSpider	10772 Y
ECHA InfoCard	100.008.414
EC Number	209-254-9
PubChem	11246
RTECS number	AJ4100000
UNII	19PPS85F9H Y
InChI InChI=1S/C2H4O2.Ag/c1-2(3)4;/h1H3,(H,3,4);/q;+1/p-1 Y Key: CQLFBEKRDQMJLZ-UHFFFAOYSA-M Y InChI=1/C2H4O2.Ag/c1-2(3)4;/h1H3,(H,3,4);/q;+1/p-1 Key: CQLFBEKRDQMJLZ-REWHXWOFAJ
SMILES CC(=O)[O-].[Ag+]
Properties
Chemical formula	AgC2H3O2
Molar mass	166.912 g/mol
Appearance	white to slightly grayish powder slightly acidic odor
Density	3.26 g/cm3, solid
Boiling point	decomposes at 220 °C
Solubility in water	1.02 g/100 mL(20 °C)
Magnetic susceptibility (χ)	−60.4·10−6 cm3/mol
Hazards
EU classification (DSD)	not listed
NFPA 704	0 1 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Silver acetate is an inorganic compound with the empirical formula CH₃CO₂Ag (or AgC₂H₃O₂). It is a photosensitive, white, crystalline solid. It is a useful reagent in the laboratory as a source of silver ions lacking an oxidizing anion. It has been used in some antismoking drugs.

Silver acetate 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.

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.

Solid silver acetate decomposes with heat to make silver particles and various gases, depending on the atmosphere present, and decomposes at slightly lower temperatures with increasing humidity. In air, the reaction mainly goes by the following:

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.

A solution of silver acetate in pyridine absorbs hydrogen, producing metallic silver:

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 palladium-catalized and requires a slight excess of silver acetate. This reaction is shorter than previous ortho-arylation methods.

Silver acetate can be used to convert certain organohalogen compounds into alcohols. It may be used, in spite of its high cost, in instances where a mild and selective reagent is desired.

Silver acetate in combination with iodine forms the basis of the Woodward cis-hydroxylation. This reaction selectively converts an alkenes into a cis-diols.