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Thermo Scientific Chemicals
Lead(IV) acetate, 96% (dry wt.), stab. with 5-10% glacial acetic acid
CAS: 546-67-8 | C8H16O8Pb | 447.408 g/mol
化学物質識別子
CAS546-67-8
IUPAC Nameλ²-lead(2+) tetraacetate
Molecular FormulaC8H12O8Pb
InChI KeyACKFDYCQCBEDNU-UHFFFAOYSA-J
SMILES[Pb++].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O
さらに表示
仕様
スペックシート
スペックシートFormMoist crystals or powder or crystalline powder
CommentMay contain fine dark particles from the manufacturing process
Appearance (Color)White to pale cream or pale grey
Assay from Supplier's CofA≥95.0% (ex Pb; dry wt. basis, Iodometry)
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.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
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.
Solubility
Soluble in water, ethanol, chloroform, benzene, nitrobenzene, tetrachloroethane, nitric acid, hot acetic acid and hydrochloric acid.
Notes
Air and moisture sensitive. Store in cool place. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with alcohols, strong acids and strong reducing agents.
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.
Solubility
Soluble in water, ethanol, chloroform, benzene, nitrobenzene, tetrachloroethane, nitric acid, hot acetic acid and hydrochloric acid.
Notes
Air and moisture sensitive. Store in cool place. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with alcohols, strong acids and strong reducing agents.
RUO – Research Use Only
General 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.