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496383

Sigma-Aldrich

1,10-Phenanthroline-5,6-dione

97%

Synonym(s):

Stahl phd oxidant, phd

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About This Item

Empirical Formula (Hill Notation):
C12H6N2O2
CAS Number:
27318-90-7
Molecular Weight:
210.19
MDL number:
MFCD00014473
UNSPSC Code:
12352100
PubChem Substance ID:
24873053
NACRES:
NA.22

Assay

97%

mp

260 °C (dec.) (lit.)

SMILES string

O=C1C(=O)c2cccnc2-c3ncccc13

InChI

1S/C12H6N2O2/c15-11-7-3-1-5-13-9(7)10-8(12(11)16)4-2-6-14-10/h1-6H

InChI key

KCALAFIVPCAXJI-UHFFFAOYSA-N

General description

1,10-Phenanthroline-5,6-dione (phendio) forms Cu(II) and Ag(I) phendio complexes, which show potent anti-fungal and anti-cancer activity. The modification of glassy carbon (GC) electrodes with phendio complexes of transition metals leads to the catalytic oxidation of NADH at low overpotential.

Application

1,10-Phenanthroline-5,6-dione may be used in the preparation of homo- and heterometallic complexes with early transition metal ions.
A Bifunctional quinone oxidant which, when used in conjunction with Zn2+ catalysts, is used to affect the aerobic oxidation of secondary amines to a variety of value added motifs, including indoles.

Bioinspired Aerobic Oxidation of Secondary Amines and Nitrogen Heterocycles with a Bifunctional Quinone Catalyst

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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

Certificates of Analysis (COA)

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Xuyan Mao et al.
The Analyst, 136(2), 293-298 (2010-10-20)
To improve the electrocatalytic activities of carbon nanotubes (CNT) towards the oxidation of nicotinamide adenine dinucleotide (NADH), we derive them with a redox mediator, 1,10-phenanthroline-5,6-dione (PD), by the noncovalent functionalization method. The redox carbon nanotubes (PD/CNT/GC) show excellent electrocatalytic activities
Aleksandra Pinczewska et al.
Journal of the American Chemical Society, 134(43), 18022-18033 (2012-10-11)
We report the combinatorial preparation and high-throughput screening of a library of modified electrodes designed to catalyze the oxidation of NADH. Sixty glassy carbon electrodes were covalently modified with ruthenium(II) or zinc(II) complexes bearing the redox active 1,10-phenanthroline-5,6-dione (phendione) ligand
Tetsuaki Fujihara et al.
Dalton transactions (Cambridge, England : 2003), (4)(4), 645-652 (2004-07-15)
Syntheses and pH dependent electrochemical properties of aqua-ruthenium(II) complexes, [Ru(trpy)(PDA-N,N')(OH2)](ClO4)2 ([1](ClO4)2) and [Ru(trpy)(PD-N,N')(OH2)](ClO4)2 ([2](ClO4)2) (trpy = 2,2':6',2''-terpyridine, PDA = 6-acetonyl-6-hydroxy-1,10-phenanthroline-5-one, PD = 1,10-phenanthroline-5,6-dione) are presented. Treatment of [Ru(trpy)(PD-N,N')Cl](PF6) with AgClO4 in a mixed solvent of acetone and H2O selectively produced
Sudeshna Roy et al.
ChemMedChem, 3(9), 1427-1434 (2008-06-10)
Phenanthroline derivatives are of interest due to their potential activity against cancer, and viral, bacterial, and fungal infections. In a search for highly specific antitumor and antibacterial compounds, we report the activities of 1,10-phenanthroline-5,6-dione (phendione or L(1)), dipyrido[3,2-a:2',3'-c]phenazine (dppz or
Yu-Min Song et al.
Journal of inorganic biochemistry, 103(3), 396-400 (2009-01-13)
Three new solid complexes have been synthesized by the reaction of rare earth(III) nitrate with the first ligand curcumin (HL) and the second ligand 1,10-phenanthroline-5,6-dione (L') in alcohol solution (pH=6.5-7.0). The composition of the complexes has been characterized by elemental
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