Lead(IV) acetate

From Wikipedia, the free encyclopedia
  (Redirected from Lead tetraacetate)
Jump to: navigation, search
Lead(IV) acetate
Lead-tetraacetate-3D-balls.png
Names
IUPAC name
Lead(IV) acetate
Other names
Lead tetraacetate
Identifiers
CAS number 546-67-8 N
ChEBI CHEBI:77245 N
Jmol-3D images Image
PubChem 11025
Properties
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
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 is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/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