Lead tetraacetate

Base Information

• Chemical Name: Lead tetraacetate
• CAS No.: 546-67-8
• Molecular Formula: C8H12O8Pb
• Molecular Weight: 443.378
• Hs Code.: 29152900
• European Community (EC) Number: 208-908-0
• UN Number: 2291
• DSSTox Substance ID: DTXSID801047756
• Nikkaji Number: J43.169I
• Wikipedia: Lead(IV)_acetate
• Mol file: 546-67-8.mol

Synonyms:lead tetraacetate;lead tetraacetate, (203)lead-labeled

Chemical Property of Lead tetraacetate

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 13.9mmHg at 25°C
• Melting Point: 175-180 °C
• Boiling Point: 118.1°C
• Flash Point: 40°C
• PSA: 105.20000
• Density: 2.28 g/cm³
• LogP: -0.32560
• Storage Temp.: 0-6°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: Decomposition
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 0
• Exact Mass: 444.02987
• Heavy Atom Count: 17
• Complexity: 25.5
• Transport DOT Label: Poison

Purity/Quality:

95%+5%Acetic acid ^*data from raw suppliers

Lta ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N,O
• Hazard Codes: T,N,O
• Statements: 61-8-20/22-33-35-50/53-62
• Safety Statements: 53-45-60-61-36/37/39-26-17

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Metals -> Organic Acids, Metal Salts
• Canonical SMILES: CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].[Pb]
• Physical Properties: Colorless monoclinic crystals; turns pink; unstable in air; density 2.228 g/cm3 at 17°C; melts at 175°C; decomposes in cold water and ethanol; soluble in chloroform, benzene, nitrobenzene, and hot glacial acetic acid; also soluble in concentrated hydrochloric acid.
• Uses: Lead tetraacetate is used as a highly selective oxidizing agent in organic synthesis. This includes oxidation of glycols into aldehydes, preparation of cyclohexyl acetate, production of oxalic acid, and in structural analysis of sugars. Oxidation with lead tetraacetate is often used in organic syntheses, because the lead salt is highly selective in the splitting of vicinal glycols. The rate of oxidation of cis glycols is more rapid than of the trans isomers, a property widely used in the structural determination of sugars and other polyols. Lead tetraacetate readily cleaves α-hydroxy acids as oxalic acid at room temperature. Another use is the introduction of acetoxy groups in organic molecules, as in the preparation of cyclohexyl acetate and the acetoxylation of cyclohexanol. At high temperature, methylation takes place. In these reactions, the organic molecule must contain double bonds or activating substituents. Lead(IV) acetate is an important oxidizing agent and a source of acetyloxy group used in organic synthesis. For example, 1,4-dioxene is prepared from dioxane involving 2-acetoxy-1,4-dioxane as an intermediate. Similarly, it is used for the preparation of bis(trifluoromethyl)diazomethane from hexafluoroacetone hydrazone. It also reacts with alkenes, alcohols having a delta-proton and di-n-butyl d-tartrate to get gamma-lactones, cyclic ethers and n-butyl glyoxylate respectively. It induces the cleavage of 1,2-diols to the corresponding aldehydes or ketones. It is actively involved in the Kochi reaction for the decarboxylation of carboxylic acids to alkyl halides and used as an alternative reagent to bromine in the Hofmann rearrangement. Selective oxidizing agent in organic syntheses: Criegee, Angew. Chem. 53, 321 (1940); Newer Methods of Preparative Organic Chemistry (Interscience, N. Y., 1948) pp 1-17.
• 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.

Technology Process of Lead tetraacetate

There total 10 articles about Lead tetraacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

acetic anhydride (108-24-7) + acetic acid (64-19-7,77671-22-8) → lead(IV) tetraacetate (546-67-8)

Guidance literature:

With lead(II,IV) oxide;

Reference yield:

acetic acid (64-19-7,77671-22-8) → lead(IV) tetraacetate (546-67-8)

Guidance literature:

With lead(II,IV) oxide;

Reference yield:

lead(II,IV) oxide + acetic acid (64-19-7,77671-22-8) → lead(IV) tetraacetate (546-67-8) + lead(II) oxide

Guidance literature:

In acetic acid; byproducts: H2O;

DOI:10.1021/ac60003a018

upstream raw materials:

acetic anhydride

acetic acid

lead acetate

carbon disulfide

Downstream raw materials:

Glutaraldehyde

α-picoline

picoline

3-benzoyl-3,4,5-triphenyl-3H-furan-2-one

Refernces

• 1、 Swann, M. H.. "". . p. 191 - 191. Retrieved 1947.