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Merck
CN

43146

Sigma-Aldrich

1,5-Diphenyl-1,3,5-pentanetrione

≥98.0% (T)

Synonym(s):

1,3-Dibenzoylacetone

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About This Item

Linear Formula:
C6H5COCH2COCH2COC6H5
CAS Number:
Molecular Weight:
266.29
Beilstein:
2054189
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Assay

≥98.0% (T)

mp

107-109 °C

functional group

ketone
phenyl

SMILES string

O=C(CC(=O)c1ccccc1)CC(=O)c2ccccc2

InChI

1S/C17H14O3/c18-15(11-16(19)13-7-3-1-4-8-13)12-17(20)14-9-5-2-6-10-14/h1-10H,11-12H2

InChI key

MUNGMRPYTCHBFX-UHFFFAOYSA-N

General description

1,5-Diphenyl-1,3,5-pentanetrione (H2DBA, DBAc) is a symmetrical triketone.1,3,5-triketones are potential tridentate ligands and forms complexes with transition metals, lanthanides and actinides. It acts as ligand and forms binuclear cobalt complex with CoCl2.6H2O. The interaction of two intramolecular hydrogen bonds in 1,5-diphenyl-1,3,5-pentanetrione has been studied. H2DBA can be synthesized by condensation reaction between ethyl benzoate and benzoyl acetone. DBAc arranged in stretched polyethylene (PE) sheets has been investigated by infrared linear dichroism (LD) spectroscopy.

Other Notes

Versatile triketone, used e.g. for the synthesis of heterocyclic compounds; Preparation of complexes with transition metals

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Some novel triorganotin(IV) derivatives of β,δ-triketones.
Kumar A, et al.
Polyhedron, 2(9), 907-916 (1983)
Infrared linear dichroism on 1,5-diphenyl-1,3,5-pentanetrione aligned in stretched polyethylene.
Andersen KB.
Acta Chemica Scandinavica, 52, 1171-1176 (1998)
Electronic states of 1, 6, 6aλ4-trithiapentalene and its 2,5-dimethyl and 2,5-diphenylderivatives. Ultraviolet-visible linear dichroism spectroscopy and time-dependent density functional theory calculations.
Spanget-Larsen J.
Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 58(10), 2245-2255 (2002)
Reactions of metal ions with triketones. Part 2. Kinetics and mechanisms of the reactions of nickel (II) and cobalt (II) with heptane-2, 4, 6-trione in methanol-water (70: 30 v/v).
Hynes MJ and Walsh J.
J. Chem. Soc., Dalton Trans., 12, 2565-2569 (1985)
Synthesis and characterization of pyridine and 2, 6-diphenyl-pyridine ethers.
Hatz LL.
Abstracts of Papers of the American Chemical Society., 201 (1991)

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