General Description
Faintly pink wet crystals with an odor of vinegar.
Reactivity Profile
Organometallics are strongly reactive with many other groups. Incompatible with acids and bases. Organometallics are good reducing agents and therefore incompatible with oxidizing agents. Often reactive with water to generate toxic or flammable gases. Generally highly toxic. Often react on contact with tissues to give toxic products.
Air & Water Reactions
Unstable in air. Reacts with water to form brown lead dioxide and acetic acid [Merck 11th ed. 1989].
Health Hazard
Early symptoms of lead intoxication by ingestion are most commonly gastrointestinal disorders, colic, constipation, etc.; weakness, which may go on to paralysis chiefly of the extensor muscles of the wrists and less often of the ankles, is noticeable in the most serious cases. Ingestion of a large amount causes local irritation of the alimentary tract; pain, leg cramps, muscle weakness, paresthesias, depression, coma, and death may follow in 1 or 2 days. Contact causes severe irritation of eyes and can burn skin.
Fire Hazard
Behavior in Fire: Can increase the intensity of a fire when in contact with combustible material. Cool containers with plenty of water.
Description
Lead (IV) acetate or lead tetraacetate is a chemical compound with chemical formula Pb(C2H3O2)4 and is a lead salt of acetic acid. It is commercially available often stabilized with acetic acid.
Chemical Properties
Lead tetraacetate (plumbic acetate), Pb(C2H3O2)4, is a colorless, monoclinic crystalline solid that is soluble in chloroform and in hot acetic acid, but decomposes in cold water and in ethyl alcohol. Lead tetraacetate can be prepared by adding warm, water-free, glacial acetate acid to red lead, Pb3O4, and subsequent cooling. The salt decomposes with the addition of water to give PbO2, but the yield can be improved by passing in chlorine gas. Lead tetraacetate is available in laboratory quantities as colorless to faintly pink crystals stored in glacial acetic acid.
Chemical Properties
White solid
Application
Lead tetraacetate is a strong oxidizing agent, a source of acetyloxy groups and a general reagent for the introduction of lead into organolead compounds. Some of its many uses in organic chemistry :
Acetoxylation of benzylic, allylic and α-oxygen ether C-H bonds, for example the photochemical conversion of dioxane to 1,4- dioxene through the 2-acetoxy-1,4-dioxane intermediate and the conversion of α-pinene to verbenone
* Oxidation of hydrazones to diazo compounds for example that of hexafluoroacetone hydrazone to bis(trifluoromethyl)diazomethane * Aziridine formation, for example the reaction of Naminophthalimide and stilbene
* Cleavage of 1,2-diols to the corresponding aldehydes or ketones often replacing ozonolysis, for instance the oxidation of di-nbutyl d-tartrate to n-butyl glyoxylate
* Reaction with alkenes to γ-lactones
* Oxidation of alcohols carrying a δ-proton to cyclic ethers.
* Oxidative cleavage of certain allyl alcohols in conjunction with ozone.
Definition
ChEBI: An acetate salt with formula Pb(OAc)4. It is used as a selective oxidising agent in organic synthesis.
reaction suitability
reagent type: catalyst
core: lead
Safety
Lead (IV) acetate may be fatal if ingested, inhaled, or absorbed through skin. It causes irritation to skin, eyes, and respiratory tract. It is a neurotoxin. It affects the gum tissue, central nervous system, kidneys, blood, and reproductive system.
