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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

Quality Level

200

assay

97%

mp

260 °C (dec.) (lit.)

functional group

ketone

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

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
WXBD6033V
WXBD3820V
WXBD1244V
WXBC8227V
WXBC6479V

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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
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
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.
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)
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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