Tetraacetylethane

Chemical compound From Wikipedia, the free encyclopedia

Tetraacetylethane is the organic compound with the nominal formula [CH(C(O)CH3)2]2. It is a white solid that has attracted interest as a precursor to heterocycles and metal complexes. It is prepared by oxidation of sodium acetylacetonate:[1]

I2 + 2 NaCH(C(O)CH3)2 → [CH(C(O)CH3)2]2 + 2 NaI
Quick facts Names, Identifiers ...
Tetraacetylethane
Names
Other names
3,4-diacetyl-2,5-Hexanedione
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 225-718-3
UNII
  • InChI=1S/C10H14O4/c1-5(11)9(6(2)12)10(7(3)13)8(4)14/h9-10H,1-4H3
    Key: CSKRBHOAJUMOKJ-UHFFFAOYSA-N
  • CC(=O)C(C(C(=O)C)C(=O)C)C(=O)C
Properties
C10H14O4
Molar mass 198.218 g·mol−1
Appearance white solid
Density 1.305 g/cm3
Melting point 192–193 °C (378–379 °F; 465–466 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Reminiscent of the case of acetylacetone, tetraacetylethane exists as the enol, as established by X-ray crystallography. The two C3O2H rings are twisted with a dihedral angle near 90°.[2]

Many metal complexes have been prepared from the conjugate base of this ligand. One example is diruthenium(III) derivative [Ru(acac)2]2[C(C(O)CH3)2]2, which is closely related to ruthenium(III) acetylacetonate.[3]

References

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