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1,10-Phenanthroline-5,6-dione

Name: 1,10-Phenanthroline-5,6-dione
Brand: ALDRICH

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

Quality Level

200

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

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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

GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Precautionary Statements

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

Target Organs

Respiratory system

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Acid-base equilibria of various oxidation states of aqua-ruthenium complexes with 1,10-phenanthroline-5,6-dione in aqueous media.

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

High-throughput synthesis and electrochemical screening of a library of modified electrodes for NADH oxidation.

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

Phenanthroline derivatives with improved selectivity as DNA-targeting anticancer or antimicrobial drugs.

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

Electrochemical biosensors based on redox carbon nanotubes prepared by noncovalent functionalization with 1,10-phenanthroline-5,6-dione.

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

Electrocatalytic oxidation of NADH at glassy carbon electrodes modified with transition metal complexes containing 1, 10-phenanthroline-5, 6-dione ligands.

Wu Q, et al.

Analytical Chemistry, 68(20), 3688-3696 (1996)

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