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Merck
CN

496383

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
NACRES:
NA.22
PubChem Substance ID:
24873053
UNSPSC Code:
12352100
MDL number:
MFCD00014473

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Product Name

1,10-Phenanthroline-5,6-dione, 97%

InChI

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

SMILES string

O=C1C(=O)c2cccnc2-c3ncccc13

InChI key

KCALAFIVPCAXJI-UHFFFAOYSA-N

assay

97%

mp

260 °C (dec.) (lit.)

functional group

ketone

Quality Level

200

Related Categories

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

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF7569V
WXBF1497V
WXBF0256V
WXBD9305V
WXBD7386V

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M V del Pozo et al.
Analytical chemistry, 77(8), 2550-2557 (2005-04-15)
A surface-based method for the study of the interactions of DNA with redox-active 1,10-phenantroline-5,6-dione (phen-dione) osmium complexes is described. The study was carried out using gold electrodes modified with DNA via adsorption and [Os(bpy)(2)(phe-dione)](3+/2+) (bpy = 2,2'-bipyridyl) or [Os(phen)(2)(phen-dione)](3+/2+) (phen
Smita Ghosh et al.
Journal of inorganic biochemistry, 100(3), 331-343 (2006-01-18)
Complexes of the type [Co(LL)2Cl2]Cl, where LL = N,N'-ethylenediamine (en), 2,2'-bipyridine (bpy), 1,10-phenanthroline (phen), 1,10-phenanthroline-5,6-dione (phendione) and dipyrido[3,2-a:2',3'-c]phenazine (dppz) have been synthesized and characterized by elemental analyses, IR, UV-visible and NMR spectroscopy. Crystal structure of [Co(phendione)2Cl2]Cl x 0.5 HCl x
E Lorenzo et al.
Biosensors & bioelectronics, 13(3-4), 319-332 (1998-06-27)
Various strategies based on the use of chemically modified electrodes for the development of amperometric biosensors are described. Particular emphasis is placed on materials capable of catalyzing the oxidation of NADH and coupling these with enzymatic activities for biosensor construction.
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)
1, 10-Phenanthroline-5, 6-dione as a building block for the synthesis of homo-and heterometallic complexes.
Calderazzo F, et al.
Inorgorganica Chimica Acta, 330(1), 136-142 (2002)
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