84-12-8

Usage

Originator

Phanquinone ,Yick-Vic Chemicals and

Definition

ChEBI: An orthoquinone that is the 5,6-diketo derivative of 4,7-phenanthroline.

Manufacturing Process

2 parts of 6-methoxy-4:7-phenanthroline are mixed with 10 parts by volume of concentrated sulfuric acid and while cooling with a mixture of ice and sodium chloride, with 6 parts by volume of fuming nitric acid (density = 1.51), and the whole is heated for 2 h at 120°C. The reaction solution is poured on to ice, its pH value is adjusted to 7 by means of a 10 N solution of caustic soda, after standing for 2 h the whole is filtered with suction to remove the precipitate which separates, and the latter is washed with hot water. After recrystallising the product from methyl alcohol and drying it at 100°C under 0.1 mm pressure, there are obtained 1.8 parts (i.e. 90 % of the calculated yield) of 4:7-phenanthroline-5:6-quinone in the form of pale yellow crystals melting at 295°C.

Safety Profile

Poison by ingestion. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Purification Methods

The dione crystallises from MeOH. The mono-oxime forms yellow crystals from MeOH with m 250o(dec), the di-oxime forms yellow crystals from MeOH with m 300o(dec) and the mono-semihydrazone forms yellow crystals from MeOH with m 195o(dec). [Druey & Schmidt Helv Chim Acta 33 1080 1950, Beilstein 24 III/IV 1741.]

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

Upstream product

• 951-06-4 5-methoxy-[4,7]phenanthroline 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 51837-64-0 N,N'-(methoxy-p-phenylene)-bis-acetamide 
• 5307-02-8 2-methoxy-1,4-phenylenediamine 
• 66671-82-7 2-methoxy-1,4-phenylenediamine sulfate 

Downstream Products

• 100259-52-7 2-phenyl-[1,3]dioxolo[4,5-f][4,7]phenanthroline 
• 91330-41-5 [4,7]phenanthroline-5,6-diol 
• 613-45-6 2,4-Dimethoxybenzaldehyde 
• 104-87-0 4-methyl-benzaldehyde 
• 3723-32-8 3,3'-bipyridine-2,2'-dicarboxylic acid 
• 217-82-3 4,7-phenanthrolino-5,6:5’,6'-pyrazine 
• 316-06-3 Naphtho<2,3-f><4,7>phenanthroline 
• 106260-24-6 2,3-bis(o-tolyl)-2,3-dihydrofuro-<2,3-f><4,7>phenantroline 
• 54616-37-4 2.2-Diphenyl-4.7-phenanthrolino-(5.6)-1.3-dioxol 
• 54078-29-4 9H-1,8-diazafluoren-9-one 
• 109185-97-9 1,2,3,4-tetrahydro-pyrazino[2,3-f][4,7]phenanthroline 

Relevant academic research and scientific papers

Synthetic method for anti-amebic-dysentery drug phanquone

The invention discloses a synthetic method for the anti-amebic-dysentery drug phanquone. The synthetic method comprises the following steps: adding 5-hydroxy-6-methoxy-4,7-diazaphenanthrene and a potassium chloride solution into a reaction vessel, raising a solution temperature, controlling a stirring speed, and carrying out a reaction; and adding a sodium sulfate solution, raising the solution temperature, then adding a diethyl sebacate solution, adding cobaltocene powder in batches within a certain period of time, carrying out a reaction, lowering the temperature, adjusting a pH value, thencarrying out washing with a benzyl chloride solution a plurality of times, then carrying out washing with a 2,3-dimethylbutane solution a plurality of times, carrying out recrystallization in a 2,4-dichlorotoluene solution, and then carrying out dehydration with a dehydrating agent so as to obtain the finished phanquone.

Intervalence charge transfer in a "chain-like" ruthenium trinuclear assembly based on the bridging ligand 4,7-phenanthrolino-5,6: 5′,6′-pyrazine (ppz)

The IVCT characteristics of the mixed valence forms of the trinuclear complex [{Δ-Ru(bpy)2}2{Δt-Ru(bpy)(- ppz)2}]n+ (n = 7, 8; t = trans), and the diastereoisomers (meso and rac) of the dinuclear complex [{Ru(bpy)2} 2(-ppz)]5+, display a marked dependence on the nuclearity and extent of oxidation of the assemblies. The dinuclear species are classified as borderline localised-delocalised mixed valence species while the two mixed valence states of the trinuclear complex exhibit localised behaviour. One-electron oxidation of a terminal Ru centre in the trinuclear case gives rise to a broad, low intensity IVCT band for the +7 mixed valence species which is composed of two underlying Gaussian-shaped bands. The transitions are identified as adjacent and remote IVCT transitions, with the former dominating the intensity of the IVCT manifold. The +8 mixed valence species exhibits a single dominant IVCT band arising from the equivalent IVCT transitions from the central Ruii to peripheral Ruiii centres. The Royal Society of Chemistry 2006.

Facile Synthesis of Tetrapyrido[2,3-a:3′,2′-c:2″,3″-h:3?,2?-j] phenazine

The title compound, a potential ligand for transition metals, was prepared by coupling of two 4,7-phenanthroline-5,6-dione molecules in presence of ammonia under reductive conditions. A straightforward synthesis of 4,7-phenanthroline-5,6-dione is also presented.

An improved preparation of 4,7-phenanthrolino-5,6:5′,6′-pyrazine

An overall three step preparation of the bis-diimine bridging ligand 4,7-phenanthrolino-5,6:5′,6′-pyrazine (ppz, 1) from 2-methoxy-l,4-phenylenediamine hydrosulfate 4 is reported.