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185191

Sigma-Aldrich

Lead(IV) acetate

reagent grade, 95%

Synonym(s):

Lead tetraacetate, Pb(acac)4

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About This Item

Linear Formula:
Pb(CH3CO2)4
CAS Number:
546-67-8
Molecular Weight:
443.38
Beilstein/REAXYS Number:
3595640
EC Number:
208-908-0
MDL number:
MFCD00008693
UNSPSC Code:
12352302
eCl@ss:
38140424
PubChem Substance ID:
329751682

grade

reagent grade

Quality Level

200

assay

95%

form

crystalline powder
powder, crystals or chunks

reaction suitability

reagent type: catalyst
core: lead

storage temp.

2-8°C

SMILES string

CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O

InChI

1S/4C2H4O2.Pb/c4*1-2(3)4;/h4*1H3,(H,3,4);/q;;;;+4/p-4

InChI key

JEHCHYAKAXDFKV-UHFFFAOYSA-J

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General description

Lead(IV) acetate is an inorganic lead salt. It participates in α-acetoxylation of ketones and oxidative decarboxylation of carboxylic acids. It along with an ionic halide (particularly chloride) salt participates in the decarboxylation of acids to afford alkyl chlorides. It affords the corresponding α,β-unsaturated γ-acetoxy-γ-lactones via reaction with 2-(trimethylsiloxy)furans.

Application

Lead(IV) acetate (LTA) may be used as an oxidizing reagent for the oxidation of following compounds:
  • unsaturated and aromatic hydrocarbons
  • monohydroxylic and saturated alcohols
  • nitrogen-containing compounds
It may be used for the following conversions:
  • Aromatic primary amines to symmetrical azo compounds.
  • Aliphatic primary amines to alkyl cyanides.
  • Primary amides to carbamates.
  • Hydrazones to azoacetates.
  • 2-(Trimethylsiloxy) furans to α,β-unsaturated γ-acetoxy-γ-lactones.
  • Aryl ethyl ketones to alkyl 2-arylpropanoates.
  • Acetophenones to methyl aryl acetates.
Smoothly induces the addition of difluorodiiodomethane to alkenes and alkynes.

signalword

Danger

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Repr. 1A - STOT RE 2

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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The reaction of 2-(trialkylsiloxy) furans with lead (IV) acetate. The synthesis of dl-pyrenophorin.
Asaoka M, et al.
Bulletin of the Chemical Society of Japan, 53(4), 1061-1064 (1980)
Facile synthesis of alkyl 2-arylpropanoates from aryl ethyl ketones using lead (IV) acetate.
Fujii K, et al.
Synthesis, 1982(06), 456-457 (1982)
Lead (IV) Acetate.
Mihailovic ML, et al.
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2005)
A new method for Halodecarboxylation of Acids using Lead (IV) acetate.
Kochi JK.
Journal of the American Chemical Society, 87(11), 2500-2502 (1965)
One-Step Synthesis of Methyl Arylacetates from Acetophenones Using Lead (IV) Acetate.
Myrboh B, et al.
Synthesis, 1981(02), 126-127 (1981)
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