2,4,6-Heptanetrione

Last updated
2,4,6-Heptanetrione
2,4,6-heptanetrione.svg
Names
Other names
diacetylacetone
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C7H10O3/c1-5(8)3-7(10)4-6(2)9/h3-4H2,1-2H3
    Key: CTHCTLCNUREAJV-UHFFFAOYSA-N
  • CC(=O)CC(=O)CC(=O)C
Properties
C7H10O3
Molar mass 142.154 g·mol−1
Appearancewhite solid
Melting point 49 °C (120 °F; 322 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2,4,6-Heptanetrione is the organic compound with the formula OC(CH2C(O)CH3)2. It is an white or colorless solid. The molecule, which exists mainly in the enol form, undergoes condensation with 1,2-diketones. [1] The compound contributes to the flavor of strawberries. [2] It forms a variety of metal complexes. [3]

See also

Refercences

  1. Scott, Lawrence T.; Cheng, Pei-Chao; Hashemi, Mohammed M.; Bratcher, Matthew S.; Meyer, Dayton T.; Warren, Hope B. (1997). "Corannulene. A Three-Step Synthesis1". Journal of the American Chemical Society. 119 (45): 10963–10968. doi:10.1021/ja972019g.
  2. Zabetakis, I. (2000). "The effect of high hydrostatic pressure on strawberry flavour compounds". Food Chemistry. 71: 51–55. doi:10.1016/S0308-8146(00)00124-2.
  3. Murtha, D. P.; Lintvedt, Richard L. (1970). "Bis(1,3,5-triketonato)dicopper(II)chelates. Ferromagnetic and antiferromagnetic exchange between copper(II) ions". Inorganic Chemistry. 9 (6): 1532–1535. doi:10.1021/ic50088a046.

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Metal acetylacetonates are coordination complexes derived from the acetylacetonate anion (CH
3
COCHCOCH
3
) and metal ions, usually transition metals. The bidentate ligand acetylacetonate is often abbreviated acac. Typically both oxygen atoms bind to the metal to form a six-membered chelate ring. The simplest complexes have the formula M(acac)3 and M(acac)2. Mixed-ligand complexes, e.g. VO(acac)2, are also numerous. Variations of acetylacetonate have also been developed with myriad substituents in place of methyl (RCOCHCOR′). Many such complexes are soluble in organic solvents, in contrast to the related metal halides. Because of these properties, acac complexes are sometimes used as catalyst precursors and reagents. Applications include their use as NMR "shift reagents" and as catalysts for organic synthesis, and precursors to industrial hydroformylation catalysts. C
5
H
7
O
2
in some cases also binds to metals through the central carbon atom; this bonding mode is more common for the third-row transition metals such as platinum(II) and iridium(III).

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