ChemicalBook Product Catalog Chemical Reagents Organic reagents Polycyclic compound 1 10-PHENANTHROLINE-5 6-DIONE 97

1 10-PHENANTHROLINE-5 6-DIONE 97

Product Name1 10-PHENANTHROLINE-5 6-DIONE 97
CAS27318-90-7
MFC12H6N2O2
MW210.19
EINECS
MOL File27318-90-7.mol

Chemical Properties

Melting point	260 °C (dec.)(lit.)
Boiling point	456.1±20.0 °C(Predicted)
Density	1.444±0.06 g/cm3(Predicted)
storage temp.	Sealed in dry,Room Temperature
pka	0.26±0.20(Predicted)
form	powder to crystal
color	Light yellow to Amber to Dark green
Water Solubility	Insoluble in water.
λmax	251nm(MeOH)(lit.)
InChI	InChI=1S/C12H6N2O2/c15-11-7-3-1-5-13-9(7)10-8(12(11)16)4-2-6-14-10/h1-6H
InChIKey	KCALAFIVPCAXJI-UHFFFAOYSA-N
SMILES	N1C2=C(C(=O)C(=O)C3=C2N=CC=C3)C=CC=1

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-36
WGK Germany	3
HS Code	29349990
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Usage And Synthesis

Chemical Properties

Yellow solid

Uses

1,10-Phenanthroline-5,6-dione is 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.

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.

Synthesis

66-71-7

27318-90-7

1. Add 35 mL of concentrated H2SO4 to a 250 mL three-necked flask at 0 °C. 2. 2. 1,10-phenanthroline (2.5 g, 28 mmol) was added slowly to the three-necked flask. 3. KBr (5 g, 42 mmol) and HNO3 (17.5 mL) were added sequentially at 5 °C. 4. Stir the reaction mixture at room temperature for 20 minutes. 5. Warm the reaction system to 130 °C and hold for 2 hours. 6. Slowly pour the hot yellow reaction solution into 150 g of ice water. 7. Neutralize to pH=7 with Na2CO3. 8. Extract the reaction mixture with CHCl3. 9. Combine the organic phases and dry with anhydrous Na2SO4. 10. Concentrate the organic phase under pressure. 11. purify the crude product by recrystallization from anhydrous ethanol to give 2.4 g (96% yield) of 1,10-phenanthroline-5,6-dione.

References

[1] Dalton Transactions, 2016, vol. 45, # 41, p. 16366 - 16378
[2] Chemistry - A European Journal, 2012, vol. 18, # 50, p. 16061 - 16072
[3] Russian Journal of Organic Chemistry, 2005, vol. 41, # 11, p. 1690 - 1693
[4] Journal of the American Chemical Society,
[5] Journal of the American Chemical Society, 2009, vol. 131, p. 4 - 5

1 10-PHENANTHROLINE-5 6-DIONE 97

Chemical Properties

Safety Information

Usage And Synthesis

Preparation Products And Raw materials

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