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Lead tetraacetate

Base Information Edit
  • 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
Lead tetraacetate

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

Suppliers and Price of Lead tetraacetate
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • AK Scientific
  • Lead(IV)tetraacetate(stabilizedwith5-10%aceticacid)
  • 1g
  • $ 10.00
  • Alfa Aesar
  • Lead(IV) acetate, 96% (dry wt.), stab. with 5-10% glacial acetic acid
  • 100g
  • $ 60.50
  • Alfa Aesar
  • Lead(IV) acetate, 96% (dry wt.), stab. with 5-10% glacial acetic acid
  • 250g
  • $ 111.00
  • Alfa Aesar
  • Lead(IV) acetate, 96% (dry wt.) stab. with 5-10% glacial acetic acid
  • 500g
  • $ 189.00
  • Alfa Aesar
  • Lead(IV) acetate, 96% (dry wt.), stab. with 5-10% glacial acetic acid
  • 1000g
  • $ 345.00
  • Biorbyt Ltd
  • LTA
  • 10 μg
  • $ 290.70
  • Chem-Impex
  • Lead(IV)acetate,98%(Assaytitration) 98%(Assaytitration)
  • 1KG
  • $ 291.20
  • Chem-Impex
  • Lead(IV)acetate,98%(Assaytitration) 98%(Assaytitration)
  • 5KG
  • $ 1288.00
  • Chem-Impex
  • Lead(IV)acetate,≥98%(Assaytitration)Hazmat ≥98%(Assaytitration)
  • 10KG
  • $ 2609.16
  • Chem-Impex
  • Lead(IV)acetate,98%(Assaytitration) 98%(Assaytitration)
  • 250G
  • $ 78.40
Total 76 raw suppliers
Chemical Property of Lead tetraacetate Edit
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

Lead(IV)tetraacetate(stabilizedwith5-10%aceticacid) *data from reagent suppliers

Safty Information:
  • Pictogram(s): ToxicT,DangerousN,Oxidizing
  • 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]
  • General Description Lead tetraacetate (LTA) is a versatile oxidizing agent used in organic synthesis for reactions such as Wessely oxidation, chlorodecarboxylation, and the oxidation of N-aroylhydrazones to form aromatic o-diketones. It facilitates radical-based transformations, including the generation of α-acetoxyglycine residues from serine or threonine in peptides, enabling further modifications. While effective in certain oxidative processes, it is outperformed by sodium periodate in cleaving unsaturated α-ketols. LTA is also employed in the synthesis of complex natural product scaffolds, such as caged xanthonoids and aflatoxin intermediates, demonstrating its utility in constructing challenging molecular architectures. However, its reactivity depends on the substrate and reaction conditions, often requiring careful optimization.
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:
Guidance literature:
With lead(II,IV) oxide;
Guidance literature:
With lead(II,IV) oxide;
Guidance literature:
In acetic acid; byproducts: H2O;
DOI:10.1021/ac60003a018
Refernces Edit

Construction of the 3-prenyl-4-oxa-tricyclo[4.3.1.03,7]dec-8-en-2-one core of caged xanthonoid natural products via tandem Wessely oxidation-intramolecular [4+2] cycloaddition

10.1016/j.tetlet.2007.11.050

The research focuses on the construction of the 3-prenyl-4-oxa-tricyclo[4.3.1.03,7]dec-8-en-2-one core, which is a key structural component found in caged xanthonoid natural products derived from Garcinia plants. The purpose of the study was to develop a two-step protocol utilizing tandem Wessely oxidation and intramolecular Diels–Alder reaction to access this core structure efficiently. The researchers successfully demonstrated the generality of this method through various examples, showing that the prenyl group could be installed in the required position. They also showed that these tricyclic scaffolds could be further transformed into substituted c-lactones through a photochemical 1,3-acyl shift and decarbonylation. Key chemicals used in the process include lead tetraacetate (LTA), acrylic acid, and various prenylated and oxygenated aromatic precursors. The study concluded that this two-step sequence is a versatile method for accessing the caged tricyclic system present in Garcinia xanthonoids and that the synthesized 4-oxa-tricyclo[4.3.1.03,7]dec-8-en-2-ones are valuable precursors for synthetically useful c-lactones.

Cleavage of Unsaturated α-Ketols to ω-Oxo-α,β-unsaturated Acids

10.1021/jo00060a040

The research focuses on the cleavage of unsaturated α-ketols to o-oxo-α,β-unsaturated acids, with the aim of developing an enantioselective synthesis of cyclic systems bearing contiguous quaternary centers, particularly those with gem-dimethyl groups. The study concludes that sodium periodate is the most effective reagent for this cleavage, outperforming other common oxidizing agents like sodium bismuthate, manganese dioxide, and lead tetraacetate, in terms of yield and efficiency. The combination of this cleavage reaction with a rhodium(I)-mediated decarbonylation of o-oxo-α,β-unsaturated esters derived from polycyclic systems was found to be a successful approach for the synthesis of the desired cyclic systems. Key chemicals used in the process include sodium periodate, sodium bismuthate, manganese dioxide, lead tetraacetate, and various α-ketols, among others, with the research providing detailed procedures and spectral data for the synthesized compounds.

A Formal Synthesis of Aflatoxin B2

10.1039/c39880000721

This research aims to develop a synthetic route for Aflatoxin B2, a highly toxic and carcinogenic metabolite produced by various Aspergillus species. The study focuses on synthesizing a ring A differentiated tetrahydrofurobenzofuran intermediate, which can be converted into Aflatoxin B2. Key chemicals used in the research include 3,5-dimethoxy phenol, ortho-iodophenol, lead tetra-acetate (LTA), di-isobutylaluminum hydride (DIBAL-H), and t-butyl mercaptide. The researchers successfully synthesized the intermediate compound through a series of reactions, including iodination, reduction, and cyclization, achieving an overall yield of approximately 4%. The study concludes that the synthesized intermediate can be further converted into Aflatoxin B2, demonstrating a feasible synthetic pathway. The research also highlights the challenges in differentiating the oxygen substituents on ring A and presents a method to selectively demethylate the intermediate using t-butyl mercaptide, achieving improved selectivity and yield. This work represents a significant advancement in the synthesis of aflatoxins and lays the foundation for further studies on their structure and toxicity.

Reactivities of stable rotamers. XXXII. chlorodecarboxylation of 3-(1,4- dimethyl-9-triptycyl)-3-methylbutanoic acid rotamers

10.1246/bcsj.66.3790

The study investigates the chlorodecarboxylation of 3-(1,4-dimethyl-9-triptycyl)-3-methylbutanoic acid rotamers (ap-1 and sc-1) using lead(IV) acetate in benzene, with lithium chloride or benzyltriethylammonium chloride as chloride sources. The ap-isomer produces a chloride (ap-2) and a cyclized compound (3) through radical addition to a nearby benzene ring, while the sc-isomer forms a benzylic chloride (4) via hydrogen transfer from the benzylic position to the radical site in the 9-substituent, along with an acetonyl ester (5) and small amounts of a 1-acetoxymethyl compound (6) and an olefin (7). The study explores the effects of varying chloride source concentrations on product distributions and proposes mechanisms for the formation of these compounds based on the stability of the benzylic radical and participation of a methyl group.

Synthesis and biological evaluation of isoflavone analogues from Dalbergia oliveri

10.1016/j.tet.2007.10.030

The research focuses on the synthesis and biological evaluation of isoflavone analogues derived from Dalbergia oliveri, a plant used in traditional Thai medicine for treating chronic ulcers. The purpose of the study was to investigate the potential of these compounds as mitosis inhibitor agents, specifically their cytotoxic effects against leukemia cell lines, their ability to inhibit microtubule assembly, and their antimicrobial activity. The researchers synthesized mucronulatol 1, violanone 2, and isoflavone 3 using an aryllead-mediated coupling reaction, which involved organolead reagents. The conclusions drawn from the study were that mucronulatol 1 exhibited significant cytotoxicity against the HBL100 leukemia cell line with an IC50 value of 5.7 mM, while all compounds modestly inhibited microtubule assembly, independent of their cytotoxic abilities. However, none of the compounds showed antibacterial activity, but were potent inhibitors of Fusarium oxysporum, a phytopathogenic fungal growth. The chemicals used in the synthesis process included 3-phenylthio-chroman-4-one, mucronulatol, violanone, and various reagents such as lead tetraacetate, tin compounds, and palladium on charcoal, among others.

OXIDATION OF N-AROYLHYDRAZONES OF o-HYDROXYARYL KETONES WITH LEAD(IV)ACETATE: A FACILE ROUTE TO AROMATIC o-DIKETONES

10.1016/S0040-4039(00)96497-9

The research explores a synthetic route to aromatic o-diketones through the oxidation of N-aroylhydrazones of o-hydroxyaryl ketones using lead(IV) acetate (LTA). The purpose of the study was to investigate the potential of this oxidation reaction as a method for synthesizing o-diketones, which are valuable intermediates in the synthesis of various heterocyclic compounds. The researchers found that the reaction was efficient, yielding high-quality o-diketones with good yields. Key chemicals used in the study include N-aroylhydrazones of o-hydroxyaryl ketones as starting materials and lead(IV) acetate as the oxidizing agent. The study concluded that this method is superior to previous methods due to its simplicity, accessibility of starting materials, and high yields, making it a synthetically useful route for the preparation of o-diketones.

Generation of α-Acetoxyglycine Residues within Peptide Chains: A New Strategy for the Modification of Oligopeptides

10.1016/S0040-4020(01)88040-6

The study presents a novel method for introducing electrophilic glycine equivalents into peptides by converting serine and threonine residues into a-acetoxyglycine derivatives using lead tetraacetate. The a-acetoxyglycine derivatives can then be reacted with various nucleophiles such as thiols, dithiols, and carbohydrates to modify peptide chains. The study also explores the conversion of these derivatives into more reactive chlorides and their subsequent reactions with amino acid esters and enamines, yielding peptides with modified amino acids and demonstrating high stereoselectivity. The method allows for the synthesis of peptides with unique polarities and structures, such as macrocycles and pseudopeptides, and is applicable even in the presence of oxidation-sensitive amino acids, with only histidine and tyrosine requiring side-chain protection.

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