lead(4+) ion tetraacetate

• ChemBase ID: 295365
• Molecular Formular: C8H12O8Pb
• Molecular Mass: 443.37608
• Monoisotopic Mass: 444.02986934
• SMILES: CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].[Pb+4]
• Canonical SMILES: [O-]C(=O)C.[O-]C(=O)C.[O-]C(=O)C.[O-]C(=O)C.[Pb+4]
• InChI: InChI=1S/4C2H4O2.Pb/c4*1-2(3)4;/h4*1H3,(H,3,4);/q;;;;+4/p-4
• InChIKey: JEHCHYAKAXDFKV-UHFFFAOYSA-J

NAMES AND DATABASE IDS

Names

• IUPAC name: lead(4+) ion tetraacetate
• IUPAC Traditional name: lead(4+) ion tetraacetate
• Synonyms: Lead tetraacetate; Lead(IV) acetate; 乙酸铅(IV)

Database IDs

• CAS Number: 546-67-8
• EC Number: 208-908-0
• MDL Number: MFCD00008693
• Beilstein Number: 3595640
• Merck Index: 145423
• PubChem SID: 180680896
• PubChem CID: 9846230

CALCULATED PROPERTIES

• Acid pKa: 4.54344
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -1.2242727
• LogD (pH = 7.4): -2.9968748
• Log P: -0.22334571
• Molar Refractivity: 23.4808 cm^3
• Polarizability: 4.912116 Å^3
• Polar Surface Area: 40.13 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 175°C
• Density: 2.28

Safety Information

• Storage Warning: Moisture Sensitive
• RTECS: AI5300000
• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: UN1616
• Hazard Class: 6.1
• Packing Group: III
• Risk Statements: 61-20/22-33-62-50/53
• Safety Statements: 53-45-60-61
• TSCA Listed: 是
• GHS Pictograms: GHS07; GHS08; GHS09
• GHS Hazard statements: H360-H373-H400-H410-H302-H332
• GHS Precautionary statements: P260-P261-P281-P304+P340-P405-P501A

Product Information

• Purity: 96% (dry wt.), stab. with 5-10% glacial acetic acid

REFERENCES

• Versatile oxidizing agent and source of acetoxy radicals. For a review of one-step acetoxylation at carbon, see: Synthesis, 567 (1973). See also: M. Hudlicky, Oxidations in Organic Chemistry, ACS Monograph 186, Washington DC (1990). Oxidizes silyl enol ethers to ɑ-acetoxycarbonyl compounds in high yields: Tetrahedron, 39, 861 (1983). In combination with a metal halide, enol ethers are similarly converted to ɑ-halocarbonyl compounds: Synthesis, 1021 (1982).
• Cleaves vic-glycols to carbonyl compounds; see, e.g.: Org. Synth. Coll., 4, 124 (1963).
• N-Formylanilines are oxidized to isocyanates. In the presence of methanol, the reaction affords the methyl urethanes directly: Synthesis, 225 (1982).
• Carboxylic acids undergo oxidative decarboxylation; review: Org. React., 19, 279 (1972). In the presence of LiCl, the alkyl chloride is obtained (Kochi reaction): J. Am. Chem. Soc., 87, 2500 (1965); Synth. Commun., 20, 1011 (1990). Yields are lower for the bromide and iodide, cf Hunsdiecker reaction (see Mercury(II) oxide, A16157). Use of NCS allows successful scale-up: Synthesis, 493 (1973).
• Intramolecular oxidative cyclization of alcohols with the reagent leads to tetrahydrofurans or tetrahydropyrans, a useful method for the functionalization of remote positions; review: Synthesis, 279 (1970). For a review of the hypoiodite method for the functionalization of remote positions such as the angular methyl groups of steroids, e.g. by reaction with lead tetraacetate and iodine, see: Synthesis, 501 (1971). For use in the synthesis of protoadamantane, see: Org. Synth. Coll., 6, 958 (1988). Compare Iodosobenzene diacetate, B24531.
• -Hydroxystannanes undergo oxidative fragmentation in a synthesis of unsaturated macrolides: Org. Synth. Coll., 8, 562 (1993).
• For use in dichloroacetic acid for the plumbation of activated aromatics to form aryllead(IV) triacetates, which are useful arylating agents for active methylene groups under very mild conditions, see: Org. Synth. Coll., 7, 229 (1990). For N-arylation of amides, see: J. Org. Chem., 61, 5865 (1996). Arylboronic acids also give aryllead(IV) triacetates, used in situ for electrophilic arylation: J. Chem. Soc., Perkin 1, 715 (1990). For a review of the use of organolead(IV) triacetates in synthesis, see: Pure Appl. Chem., 68, 819 (1996).