| Identification | Back Directory | [Name]
1 10-PHENANTHROLINE-5 6-DIONE 97 | [CAS]
27318-90-7 | [Synonyms]
phen-5,6-dione
Stahl phd oxidant
Phenanthroline-5,6-
dipyridobenzoquinone
Stahl phd oxidant phd
1,10-Phenanthrolin-5,6-dione
1,1-Phenanthroline-5,6-dione
1,10-Phenanthroline-5,6-dione
5H-cyclopenta dipyridin-5-one
1,10-Phenanthroline-5,6-quinone
1 10-PHENTHROLINE-5 6-DIONE 97
1,10-Phenanthroline-5,6-dione>
1,10-Phenanthroline-5,6-dione 97%
1 10-PHENANTHROLINE-5 6-DIONE 97
11,10-Phenanthroline-5,6-dione, 98%
5,6-dihydro-1,10-phenanthroline-5,6-dione
5,6-Dihydro-5,6-dioxo-1,10-phenanthroline
1,10-Phenanthroline-5,6-dione, 98%
Yellow to orange solid | [Molecular Formula]
C12H6N2O2 | [MDL Number]
MFCD00014473 | [MOL File]
27318-90-7.mol | [Molecular Weight]
210.19 |
| Chemical Properties | Back Directory | [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 |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Ethanol-->Sodium hydroxide-->Sulfuric acid-->Nitric acid-->Chloroform-->Stannous chloride dihydrate-->Potassium bromide-->o-Phenanthroline-->1,10-Phenanthroline hydrate | [Preparation Products]
4,5,9,16-tetraaza-dibenzo[a,c]naphthacene-->2-(4-trifluoroMethylphenyl)iMidazole[4,5f][1,10]phenanthroline-->2-(2-trifluoroMethylphenyl)iMidazole[4,5f][1,10]phenanthroline-->2-(3-trifluoroMethylphenyl)iMidazole[4,5f][1,10]phenanthroline-->6-(4-METHOXYPHENYL)-2,2-DIMETHYL-[1,3]DIOXOLO[4,5-F][1,10]PHENANTHROLINE-->11,12-dimethyldipyrido[3,2-a:2',3'-c]phenazine-->tetrapyrido[3,2-a:2',3'-c:3'',2''-h:2''',3'''-j]phenazine |
| Hazard Information | Back Directory | [Chemical Properties]
Yellow solid | [Uses]
A Bifunctional quinone oxidant | [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 |
|
|