1 10-PHENANTHROLINE-5 6-DIONE 97 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

form 

powder to crystal

pka

0.26±0.20(Predicted)

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

1 10-PHENANTHROLINE-5 6-DIONE 97 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

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(27318-90-7)Related Product Information

• 2,9-Dichloro-1,10-phenanthroline
• 3,8-Dibromophenanthroline
• 2，9-dibromo-1,10-phenanthroline
• 5,6-diamino-1,10-phenanthroline
• 1,10-PHENANTHROLINE-2,9-DICARBOXYLIC ACID
• 4,7-Dimethyl-1,10-phenanthroline
• 2-METHYLNICOTINALDEHYDE
• 2,3-Lutidine
• 2,2'-Bipyridine
• 3-PROPYLPYRIDINE
• ISOAMYLAMINE
• 1 10-PHENANTHROLINE-5 6-DIONE 97
• 3-PROPIONYLPYRIDINE
• 3-ETHYL-2-METHYLPYRIDINE
• 1,10-Phenanthroline-5,6-dione,3,8-dibromo
• 3,3'-DIMETHYL-2,2'-BIPYRIDINE
• PYRIDIN-3-YLACETALDEHYDE
• 3-(2-OXO-PROPYL)-PYRIDINIUM, CHLORIDE