Ferrous acetylacetonate

CAS

14024-17-0

Catalog Number

ACM14024170

Category

Main Products

Molecular Weight

256.08

Molecular Formula

C10H16FeO4

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Specification

Synonyms

Iron acetylacetonate

Canonical SMILES

CC(=CC(=O)C)O.CC(=CC(=O)C)O.[Fe]

InChI

InChI=1S/2C5H8O2.Fe/c2*1-4(6)3-5(2)7;/h2*3,6H,1-2H3;/b2*4-3-;

InChI Key

LFKXWKGYHQXRQA-FDGPNNRMSA-N

Melting Point

175 °C

Appearance

Powder

Exact Mass

256.039795

Hydrogen Bond Acceptor Count

Hydrogen Bond Donor Count

Isomeric SMILES

C/C(=C/C(=O)C)/O.C/C(=C/C(=O)C)/O.[Fe]

Monoisotopic Mass

256.039795

Rotatable Bond Count

Topological Polar Surface Area

74.6 Å²

Ferrous Acetylacetonate for the Catalytic Synthesis of O-Heterocycles

Dong, Yuyang, et al. Journal of the American Chemical Society, 2021, 143(19), 7480-7489.

O-heterocycles can be synthesized from α-diazo-β-ketoesters via intramolecular C-H alkoxylation using ferrous acetylacetonate [Fe(acac)2] as a catalyst. The catalysis is particularly effective for the synthesis of spirocyclic ethers and fused bi- and tricyclic ethers commonly found in agrochemicals, pharmaceuticals, and natural products.
Mechanism of O-heterocycle formation via Fe catalyst
· The ketoester moieties of the substrate bind to Fe(acac)2, initiating electron transfer from the iron center. This reduction triggers dinitrogen loss, generating a high-spin Fe(III) center and a vinyl carboradical. The vinyl carboradical undergoes a 1,5-hydrogen atom transfer (HAT) with significant electron transfer (ET) character during the transition state. The resulting alkyl carboradical combines with the iron-bound keto oxygen to form the (Z)-2-alkylidene dihydrofuran product.
· Theoretical calculations suggest that the rate-determining step is N2 loss with an activation barrier of approximately 21.4 kcal/mol, consistent with room-temperature reactivity. The subsequent hydrogen atom abstraction (HAA) step is most favorable for tertiary C-H bonds, followed by barrierless radical recombination. While the calculated N2 loss barriers are similar for various substrates, experimental reactivity differences are attributed to post-RDS catalyst deactivation competing with the productive HAA step. Substrates with more reactive C-H bonds undergo HAA more competitively, resulting in faster catalytic turnovers and lower catalyst loadings.

Iminopyridine-Iron(II) Acetylacetonate Precatalysts for Stereoselective Polymerization of Isoprene

Zhao, Mengmeng, et al. Applied Organometallic Chemistry, 2019, 33(4), e4836.

A series of (aryl/alkyl)-iminopyridine iron(II)acetylacetonate [Fe(acac)2] complexes were developed, which can be used for stereoselective polymerization of isoprene via ligand control. Among them, the complex Fe2 (alkyl = CH2Ph) showed the highest activity, while Fe6-catalyzed polyisoprene with a high content of trans-1,4 units (up to 87%).
Preparation of catalysts based on iron(II)acetylacetonate
· In the beginning, ligands used (L1-L6) were 2-(phenyliminomethyl)pyridine, 2-(benzyliminomethyl)pyridine, 2-(diphenylmethyliminomethyl), 2-(isopropyliminomethyl)pyridine, 2-(tert-butyliminomethyl)pyridine, and 2-(2,4,4-trimethylpentan-2-yliminomethyl)pyridine, respectively.
· The respective ligand and Fe(acac)2 were mixed at room temperature with anhydrous dichloromethane (10 ml). This reaction mixture was heated at this same temperature for 24 hours. The reaction solution was then concentrated to 2 ml, hexane added to precipitate and the precipitate filtrated, hexane-scrubbed and vacuum dried to obtain the appropriate complex (Fe1~Fe6).
· The polymerization of isoprene in toluene, last but not least, was carried out in a 25 mL Schlenk reactor on the prepared acetylacetonate iron (II) complex (Fe1~Fe6) as catalyst.

August 15, 2023

Work great in catalytic reaction
Ferrous acetylacetonate has a special structure, which effectively catalyzes my synthesis reaction.

What is the molecular weight of Ferrous acetylacetonate?

The molecular weight of Ferrous acetylacetonate is 254.06.

What are some synonyms for Ferrous acetylacetonate?

Some synonyms for Ferrous acetylacetonate include (Acetylacetonato)iron, Bis(2,4-pentanedionato)iron, and Iron bis(acetylacetonate).

What is the melting point of Ferrous acetylacetonate?

The melting point of Ferrous acetylacetonate is 175 °C.

In what solvents is Ferrous acetylacetonate slightly soluble?

Ferrous acetylacetonate is slightly soluble in benzene and toluene.

What is the color of Ferrous acetylacetonate crystals?

The crystals of Ferrous acetylacetonate are orange-brown.