Tris(acetylacetonato)iron(III)

Tris(acetylacetonato)iron(III)
Identifiers
CAS number 14024-18-1 Y
Properties
Molecular formula Fe(C5H7O2)3
Appearance Red Solid
Density 5.24 g/cm3
Melting point

180–181 °C

Boiling point

100 °C (at 13.00 hPa)

Solubility in water 2 g/L
Hazards
R-phrases R22, R36
S-phrases S26
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Tris(acetylacetonato) iron(III), often abbreviated Fe(acac)3, is a ferric coordination complex featuring acetylacetonate (acac) ligands. It is a red air-stable solid that dissolves in nonpolar organic solvents.

Contents

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Preparation

Fe(acac)3 is prepared by treating freshly precipitated Fe(OH)3 with acetylacetone, forming deep red crystals of Fe(acac)3.[1]

Fe(OH)3 + 3 C5H8O2 → Fe(acac)3 + 3 H2O

Structure and properties

Fe(acac)3 is a paramagnetic compound with a magnetic moment of 5.90 μB. This homoleptic metal acetylacetonate has an octahedral geometry with D3 symmetry, with no apparent Jahn-Teller distortions, unlike related metal acetylacetonate Mn(acac)3.[2]

Applications

Fe(acac)3 has been exploited as a catalyst and reagent in organic chemistry, especially for reactions involving alkenes. Not only being useful in catalysis, Fe(acac)3 can be reactive. In one instance, Fe(acac)3 is used to form an intermediate en-route to the carbon-carbon bond forming reaction of cross-coupling a diene to an olefin.[3] For instance, Fe(acac)3 catalyzes the dimerization of isoprene to a mixture of 1,5-dimethyl-1,5-cyclooctadiene and 2,5-dimethyl-1,5-cyclooctadiene.[4]

Fe(acac)3 also catalyzes the ring-opening polymerization of 1,3-benzoxazine.[5] Beyond the area of polymerization, Fe(acac)3 has been found to catalyze the reaction of N-sulfonyl oxaziridines with olefins to form 1,3-oxazolidine products.[6]

References

  1. ^ US patent 2004012769, Chaudhari, Mihir Kanti et al, "Process for making metal acetylacetonates", issued 2004-07-01 
  2. ^ Lawson, K.E. (1961). "The infrared absorption spectra of metal acetylacetonates.". Spectrochimica Acta 17: 248–258. doi:10.1016/0371-1951(61)80071-4. 
  3. ^ Takacs, J. A., L.; Madhavan, G.V.; Creswell, M.; Seely, F.; Devroy, W. (1986). "Iron-Catalyzed Aminohydroxylation of Olefins". Organometallics 5 (11): 2395–2398. doi:10.1021/om00142a044. 
  4. ^ Misono, A. (1966). "Oligomerization of isoprene by cobalt or iron complex catalysts.". Bulletin of the Chemical Society of Japan 39 (11): 2425. doi:10.1246/bcsj.39.2425. 
  5. ^ Sudo, A.; Hirayama, Shoji; Endo, Takeshi (2010). "Highly efficient catalysts-acetylacetonato complexes of transition metals in the 4th period for ring-opening polymerization of 1,3-benzoxazine". Journal of polymer science. Part A, Polymer chemistry 48 (2): 479. doi:10.1002/pola.23810. 
  6. ^ Williamson, K. T.; Yoon, T. (2010). "Iron-Catalyzed Aminohydroxylation of Olefins". J. Am. Chem. Soc. 132 (13): 4570–4571. doi:10.1021/ja1013536. PMC 2857537. PMID 20232850. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2857537.