Lead(IV) acetate

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Lead(IV) acetate
Lead-tetraacetate-3D-balls.png
Identifiers
CAS number 546-67-8 YesY
PubChem 11025
ChEBI CHEBI:77245 N
Jmol-3D images Image 1
Properties
Molecular formula Pb(C2H3O2)4
Molar mass 443.376 g/mol
Appearance colorless or pink crystals
Odor vinegar
Density 2.228 g/cm3 (17 °C)
Melting point 175 °C (347 °F; 448 K)
Boiling point decomposes
Solubility in water reacts with water
Solubility reacts with ethanol
soluble in chloroform, benzene, nitrobenzene, hot acetic acid, HCl, tetrachloroethane
Hazards
Main hazards Toxic
NFPA 704
Flammability code 0: Will not burn. E.g., water Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Lead(IV) acetate or lead tetraacetate is a chemical compound with chemical formula Pb(C2H3O2)4 and is a lead salt of acetic acid. It is commercially available often stabilized with acetic acid.

Structure[edit]

In the solid state the lead atoms are surrounded by four acetate ions which are bidentate, each coordinating via two oxygen atoms. The lead atom is 8 coordinate and the O atoms form a flattened trigonal dodecahedron.[1]

Preparation[edit]

It can be prepared by reaction of red lead with acetic acid.[2][3] The other main lead acetate is lead(II) acetate.

Reagent in organic chemistry[edit]

Lead tetraacetate is a strong oxidizing agent,[3] a source of acetyloxy groups and a general reagent for the introduction of lead into organolead compounds. Some of its many uses in organic chemistry:

oxidative cleavage of allyl alcohols

Safety[edit]

Lead(IV) acetate may be fatal if ingested, inhaled, or absorbed through skin. It causes irritation to skin, eyes, and respiratory tract. It is a neurotoxin. It affects the gum tissue, central nervous system, kidneys, blood, and reproductive system.

References[edit]

  1. ^ Schürmann, M.; Huber, F. (1994). "A redetermination of lead(IV) acetate". Acta Crystallographica Section C Crystal Structure Communications 50 (11): 1710–1713. doi:10.1107/S0108270194006438. ISSN 0108-2701. 
  2. ^ Inorg. Synth, 1, 47 (1939).
  3. ^ a b J. Zýka (1966). "Analytical study of the basic properties of lead tetraacetate as oxidizing agent". Pure and Applied Chemistry 13 (4): 569–581. doi:10.1351/pac196613040569. Retrieved 19 December 2013. 
  4. ^ Organic Syntheses, Vol. 82, p.99 (2005) Article.
  5. ^ Organic Syntheses, Coll. Vol. 9, p.745 (1998); Vol. 72, p.57 (1995) Article
  6. ^ Baumgarten, Henry; Smith, Howard; and Staklis, Andris (1975). "Reactions of amines. XVIII. Oxidative rearrangement of amides with lead tetraacetate". The Journal of Organic Chemistry 40 (24): 3554–3561. doi:10.1021/jo00912a019. Retrieved 19 December 2013. 
  7. ^ Organic Syntheses, Coll. Vol. 6, p.161 (1988); Vol. 50, p.6 (1970) Article.
  8. ^ Organic Syntheses, Coll. Vol. 6, p.56 (1988); Vol. 55, p.114 (1976) Link
  9. ^ Organic Syntheses, Coll. Vol. 4, p.124 (1963); Vol. 35, p.18 (1955) Article.
  10. ^ M B Smith, J March. March's Advanced Organic Chemistry (Wiley, 2001) (ISBN 0-471-58589-0)
  11. ^ O3/Pb(OAc)4: a new and efficient system for the oxidative cleavage of allyl alcohols E.J. Alvarez-Manzaneda R. Chahboun , M.J. Cano, E. Cabrera Torres, E. Alvarez, R. Alvarez-Manzaneda, b, A. Haidour and J.M. Ramos López Tetrahedron Letters Volume 47, Issue 37 , 11 September 2006, Pages 6619-6622 doi:10.1016/j.tetlet.2006.07.020
  12. ^ Conversion of 1-allyl-cyclohexanol to cyclohexanone, in the proposed reaction mechanism the allyl group is first converted to a trioxalane according to conventional ozonolysis which then interacts with the alkoxy lead group
  13. ^ Synthesis 1981, 2, 126-127.
  14. ^ A New Method for Halodecarboxylation of Acids Using Lead(IV) Acetate Jay K. Kochi J. Am. Chem. Soc.; 1965; 87(11); 2500–02. doi:10.1021/ja01089a041