o-Phenanthroline CAS 66-71-7
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- Appearance: White powder
- Assay: 99. 0%min
- Stock: In stock
- Sample: Available
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o-Phenanthroline: The Complete Guide
o-Phenanthroline for Sale
Basic Info of o-Phenanthroline
1,10-Phenanthroline anhydrous; 1,10-Phenanthroline; Ortho-phenanthroline
Pharmaceutical intermediates; Organic raw materials
What is o-Phenanthroline?
O-phenanthroline is an organic compound with molecular formula C12H8N2. The solid is white crystal and dissolves in water to form a light yellow to yellow solution. When recrystallized with water, it contains a crystal water molecule. The o-phenanthroline hydrate is a white crystal. When recrystallized with benzene, there is no crystal water, and the melting point is 98-100 ℃ (117 ℃). The boiling point is above 360 ℃. Soluble in ethanol, benzene and acetone, insoluble in petroleum ether. It forms complexes with iron, copper, cobalt, nickel and 2,2-BIPYRIDINE, forms red complexes with Fe2 +, and oxidizes with potassium permanganate to obtain 2,2-bipyridine-3,3 ‘- dicarboxylic acid.
O-phenanthroline is a common redox indicator. It is a bidentate heterocyclic compound ligand, similar to 2,2-BIPYRIDINE. It is a common auxiliary ligand in the construction of crystal materials. It has a strong chelating property and can form very stable complexes with most metal ions. It can be used as a quantitative colorimetric reagent for copper and iron, and also as an indicator for cerium sulfate titration of iron salts; It can also be used as a dye for animal fibers.
O-phenanthroline can form facilities with different transition metals. Given that the complicateds created are chelate complexes, they are fairly steady. The complicateds and also their by-products formed with copper can be used as non-oxidative nucleic acid cleaving enzymes because they have particular cleavage activity on DNA, and also further have specific anticancer tasks.
O-phenanthroline is a typical ligand for spectroscopic decision of steels and also spectroscopic evaluation of CO2 reduction. It is used for the cross-linking response of organic boronic acid catalyzed by Cu(II), etc. It can also be used as a redox sign as well as a reagent for the decision of ferrotitanium.
It forms facilities with iron, copper, cobalt, nickel as well as 2,2′-bipyridine, forms red facilities with Fe2+, as well as is oxidized with potassium permanganate to acquire 2,2′-dipyridyl-3,3′-dicarboxylate acid. It can be used as a measurable colorimetric reagent for copper as well as iron, and as an indication for titrating iron salts with cerium sulfate; it can likewise be used as a dye for pet fibers. The o-phenanthroline-Fe(II) indicator can be prepared by liquifying 1.485 g of o-phenanthroline monohydrate and 0.695 g of FeSO4-7H2O in 100 mL of water. Indicator for ceric sulfate titration of iron salts. A related ligand is red phenanthroline (BPT), 4,7-diphenyl-1,10-phenanthroline. O-phenanthroline can likewise be used for the analysis of the material of alkyl lithium substances. The details steps are to make the example react with a small amount (about 1 mg) of o-phenanthroline to provide a dark shade, and after that titrate with alcohol till the colorless titration end point is reached.
In the solution of pH=2 ~ 9, o-phenanthroline responds with divalent ferrous ion (Fe2+), the selectivity of this reaction is very high, and also the resulting orange-red complex is extremely secure, lgK stable = 21.3 (20 ° C), its option has an optimum absorption top at 510nm (visible light), as well as this shade reaction can be made use of to establish trace iron by visible light spectrophotometry.
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Application of o-Phenanthroline
Synthesis of 2-hydroxy-1,10-o-phenanthroline
Starting with l,10-phenanthroline, and then adding structural modifications on this basis, it is an important method to synthesize l,10-phenanthroline derivatives. The derivatives obtained in this way are mainly concentrated in 5, The 6-position, 3,8-position, 2,9-position, and the 5,6-position produced the highest number of derivatives. Derivatives of phenanthroline, as good metal ligands, are widely used in antibacterial and antitumor, catalytic reactions, supramolecular chemistry, DNA probes, molecular switches, etc. 2-Hydroxy-1,10-o-phenanthroline is an important 2-position derivative in 1,10-o-phenanthroline derivatives. The main synthesis method is through 2-halogenated-1,10-o-phenanthroline. The hydrolysis reaction is obtained. Due to the lack of access routes, there are relatively few studies on the properties and applications of 2-hydroxy-1,10-phenanthroline reported in the literature. CN201710460068.1 provides a kind of synthetic method of 2-hydroxyl-1,10-o-phenanthroline, and increases the source route of target product. For this reason, the present invention adopts the following route to synthesize 2-hydroxy-1,10-o-phenanthroline:
The reaction method takes 1,10-o-phenanthroline (2) as a starting material, reacts with benzyl halide to obtain an intermediate quaternary ammonium salt (3), and then oxidizes it with potassium ferricyanide to obtain 1-benzyl-1,10 -o-phenanthroline-2-one (4), then debenzylated under palladium-carbon catalysis to obtain 2-hydroxy-1,10-o-phenanthroline (1).
The preparation scheme of 2-hydroxy-1,10-o-phenanthroline is as follows: 1,10-o-phenanthroline (2) and benzyl halide are heated to obtain 1-benzyl-1,10-o-phenanthroline halide salt (3 ), 1-benzyl-1,10-o-phenanthroline halide salt (3) was oxidized by potassium ferricyanide in cold aqueous solution to obtain 1-benzyl-1,10-o-phenanthroline-2-one (4) ), and finally low-pressure hydrogenation in the presence of palladium-carbon catalyst to obtain 2-hydroxy-1,10-o-phenanthroline (1). The benzyl halide used in this scheme can be selected from benzyl chloride or benzyl bromide, and can also be a derivative of benzyl chloride or benzyl bromide; it is better to control the temperature at -5 to 5°C when potassium ferricyanide is oxidized; The hydrogen pressure in the case of the benzyl group may be normal pressure or a hydrogen pressure not higher than 1 MPa.
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