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A15551 Lead(IV) acetate, 96% (dry wt.), stab. with 5-10% glacial acetic acid

CAS Number
546-67-8
Synonyms
Lead tetraacetate

Stock No. Size Price ($) Quantity Availability
A15551-22 100g 55.80
A15551-30 250g 103.00
A15551-36 500g 183.00
A15551-0B 1000g 322.00
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Lead(IV) acetate, 96% (dry wt.), stab. with 5-10% glacial acetic acid

MDL
MFCD00008693
EINECS
208-908-0

Chemical Properties

Formula
C8H12O8Pb
Formula Weight
443.37
Melting point
175°
Density
2.28
Storage & Sensitivity
Moisture Sensitive. Store under Nitrogen. Ambient temperatures.
Solubility
Soluble in water, ethanol, chloroform, benzene, nitrobenzene, tetrachloroethane, nitric acid, hot acetic acid and hydrochloric acid.

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.

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.

Literature 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.

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).

-Hydroxystannanes undergo oxidative fragmentation in a synthesis of unsaturated macrolides: Org. Synth. Coll., 8, 562 (1993).

You, X.; Li, F. B.; Wang, G. W. Synthesis of Ortho Acid Ester-Type 1, 3-Dioxolanofullerenes: Radical Reaction of [60] Fullerene with Halocarboxylic Acids Promoted by Lead (IV) Acetate. J. Org. Chem. 2014, 79 (22), 11155-11160.

Sun, X.; Yang, J.; Zhang, W.; Zhu, X.; Hu, Y.; Yang, D.; Yuan, X.; Yu, W.; Dong, J.; Wang, H.; Li, L.; Vasant Kumar, R.; Liang, S. Lead acetate trihydrate precursor route to synthesize novel ultrafine lead oxide from spent lead acid battery pastes. J. Power Sources 2014, 269, 565-576.

GHS Hazard and Precautionary Statements

Hazard Statements: H302-H314-H332-H335-H350-H360Df-H373

Harmful if swallowed. Causes severe skin burns and eye damage. Harmful if inhaled. May cause respiratory irritation. May cause cancer. May damage the unborn child. Suspected of damaging fertility. May cause damage to organs through prolonged or repeated exposure.

Precautionary Statements: P201-P202-P260-P264b-P270-P271-P281-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P501c

Obtain special instructions before use. Do not handle until all safety precautions have been read and understood. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Use personal protective equipment as required. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT induce vomiting. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

Merck
14,5423
Beilstein
3595640
Hazard Class
6.1
Packing Group
III
Harmonized Tariff Code
2915.29
TSCA
Yes
RTECS
AI5300000

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