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1,10-Phenanthroline hydrate is a chemical substance with the chemical formula of C12H8N2.H2O, CAS 5144-89-8, and the monohydrate is a white crystalline powder. Soluble in 300 parts of water, 70 parts of benzene, soluble in alcohol and acetone, insoluble in petroleum ether. It is a metal chelating agent, which can prevent chromosome aberration induced by streptozotocin. It is a commonly used redox indicator. As a detection method with simple operation, low cost and fast analysis speed, o-diazophenyl colorimetry is widely used in the detection and analysis of iron. The principle is that phenanthroline and fe2+ will form a stable orange red complex chemicalbook in the solution of ph=3 ~ 9. The color depth of the complex can be used to determine the content of iron ions in the sample to be tested. Although this method has high sensitivity, it will still be affected by other components in the sample. When using this method to determine the content of substances, we need to pay attention to the experimental conditions such as the dosage of phenanthroline, pH environment, reaction time and wavelength.
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Chemical Formula |
C12H10N2O |
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Exact Mass |
136 |
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Molecular Weight |
136 |
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m/z |
198 (100.0%), 199 (13.0%) |
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Elemental Analysis |
C, 72.71; H, 5.09; N, 14.13; O, 8.07 |
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Preparation method:
1. The product can be prepared by heating o-phenylenediamine with glycerol, nitrobenzene and concentrated sulfuric acid, or using 8-aminoquinoline as raw material.
2. Stir 8-aminoquinoline, glycerol and arsenic pentoxide evenly and add concentrated sulfuric acid. Pour the reaction mixture into water and neutralize it with cold ammonia water,
The black consistency is extracted with boiling benzene and treated.
It can form complexes with a variety of transition metals. Because the formed complexes are chelates, they are relatively stable. The complexes formed with copper and their derivatives can be used as non oxidative nucleic acid cleavage enzymes because they have certain DNA cleavage activity, and then have certain anticancer activity.
Purpose: 1,10-Phenanthroline hydrate is a common ligand for spectrometric determination of metals and spectral analysis of CO 2 reduction. It is used for Cu (II) - catalyzed cross-linking reaction of organic boric acid, etc. it can also be used as oxidation-reduction indicator and reagent for the determination of ferrotitanium. It forms complexes with iron, copper, cobalt, nickel and 2,2 ′ - bipyridine, and reacts with Fe ²+ form a red complex and oxidize it with potassium permanganate to obtain 2,2 '- dipyridyl-3,3' - dicarboxylic acid. It can be used as a quantitative colorimetric reagent for copper and iron, and also as an indicator for titrating iron salt with cerium sulfate; It can also be used as a dye for animal fibers. O-phenanthroline Fe (Ⅱ) indicator can be prepared by dissolving 1.485g o-phenanthroline monohydrate and 0.695g FeSO ₄ · 7h Ψ o in 100ml water. Indicator for cerium sulfate titration of iron salt. A related ligand is red phenanthroline (BPT), 4,7-diphenyl-1,10-phenanthroline. O-phenanthroline can also be used to analyze the content of alkyl lithium compounds. The specific step is to make the sample react with a small amount (about 1mg) of o-phenanthroline to be dark, and then titrate with alcohol until the colorless titration end point is reached. In the solution with ph=2~9, o-phenanthroline and 2-valent ferrous ion (Fe ² +) color reaction occurs, and the selectivity of the reaction is very high, and the orange red complex generated is very stable, LGK stability =21.3 (20 ℃), and its solution has the maximum absorption peak at 510nm (visible light). Using this color reaction, trace iron can be determined by visible light spectrophotometry.
1,10-Phenanthroline, also known as 1,10-Phenanthroline, Phenanthroline, or Phenanthroline, is an important organic compound with unique chemical structure and properties, and has a wide range of applications in multiple fields. The following will provide a detailed description of all uses of ortho phenanthroline.
Metal ion detection and analysis
Phenanthroline plays a crucial role in metal ion detection and analysis. The two nitrogen atoms in its molecular structure are in suitable positions, which can strongly coordinate with various metal ions to form stable complexes, especially for the coordination effect of ferrous ions (Fe ² ⁺). In complex chemical systems, ortho phenanthroline can accurately identify and tightly grasp Fe ² ⁺, forming distinctive orange red complexes. This complex has a maximum absorption peak at a wavelength of 510nm. By measuring its absorbance using spectrophotometry, the content of ferrous ions in water can be quickly and accurately determined, providing key data for evaluating water quality safety.
In addition to ferrous ions, ortho phenanthroline can also be used to determine various metal ions such as palladium, vanadium, copper, iron, and titanium iron. It is a commonly used reagent for determining these metal ions and has applications in various analytical methods such as titration analysis, spectrophotometric analysis, fluorescence analysis, and electrochemical analysis. For example, ortho phenanthroline can be used as a quantitative colorimetric reagent for copper and iron, as well as an indicator for titrating iron salts with cerium sulfate.
Redox indicator
1,10-Phenanthroline hydrate is a commonly used redox indicator. The ortho phenanthrene colorimetric method, as a simple, low-cost, and fast analytical method, is widely used in the detection and analysis of iron elements. The principle is that ortho phenanthrene and Fe ² ⁺ will form a stable orange red complex in a solution with pH=3-9, and the color intensity of the complex can be used to determine the content of iron ions in the test sample. Although this method has high sensitivity, it is still affected by other components in the sample. Therefore, when using this method to determine substance content, attention should be paid to experimental conditions such as the amount of phenanthrene used, pH environment, reaction time required, and wavelength.
Surface enhanced Raman spectroscopy detection
CN201210363302.6 provides a method for surface enhanced Raman spectroscopy detection of ortho phenanthroline. This method has the advantages of good selectivity, simple and fast method, and low cost, and has good application prospects in the determination of ortho phenanthroline. Under the conditions of the present invention, the nano silver solution can be aggregated into a nano silver aggregate active substrate in a sodium dihydrogen phosphate disodium hydrogen phosphate buffer solution and a sodium chloride solution. When the ortho phenanthroline solution is added, the ortho phenanthroline adsorbs onto the surface of the nano silver aggregate and exhibits a strong surface enhanced Raman scattering peak at 1450cm ⁻¹, and the concentration of ortho phenanthroline shows a good linear relationship with the intensity enhancement of the surface enhanced Raman scattering peak. Based on this, a quantitative analysis method for determining ortho phenanthroline can be established.
Catalytic photometry, fluorescence spectroscopy, and kinetic analysis methods
The main methods for determining ortho phenanthroline include catalytic photometry, fluorescence spectroscopy, and kinetic methods. Catalytic spectroscopy utilizes the catalytic effect of ortho phenanthroline, with an analysis range between 0 and 1.0 × 10 ⁻ ³ mol/L; The fluorescence spectroscopy method utilizes the phosphorescence quenching of ortho phenanthroline to increase the analysis range to 4.0 × 10 ⁻⁷~4.0 × 10 ⁻⁵ mol/L; The kinetic method utilizes changes in reaction rate for analysis, with an analysis range between 1.0 × 10 ⁻⁸ and 6.0 × 10 ⁻⁶ mol/L. These methods provide multiple options for quantitative analysis of ortho phenanthroline, which can be selected according to specific needs and experimental conditions.
Participate in catalytic reactions as ligands
As a bidentate ligand, ortho phenanthroline can form stable ligands with various metal ions, which are widely used in catalytic reactions. For example, it can be used in the cross-linking reaction of organic boronic acid catalyzed by Cu (II), by coordinating with metal ions to change the electronic structure and reaction activity of metal ions, thereby promoting the progress of the reaction. In fields such as optoelectronics and materials science, ligands formed between ortho phenanthroline and metal ions also have important applications.
Analysis of alkyl lithium compound content
Phenanthroline can be used for the analysis of alkyl lithium compound content. The specific steps are to react the sample with a small amount (about 1mg) of ortho phenanthroline to form a dark color, and then titrate with alcohol until a colorless titration endpoint is reached. This method utilizes the characteristic of color reaction between phenanthroline and certain compounds to determine the endpoint of the reaction through color change, thereby achieving analysis of the content of alkyl lithium compounds.
Organic synthesis intermediates
Phenanthroline is an important organic synthesis intermediate that can be used as a starting material to synthesize various derivatives through structural modification. These derivatives are mainly concentrated at positions 5, 6-, 3, 8-, and 2, 9-, with the highest number of derivatives produced at positions 5, 6-. Derivatives of ortho phenanthroline are widely used as excellent metal ligands in antibacterial and anticancer activities, catalytic reactions, supramolecular chemistry, DNA probes, molecular switches, and other fields. For example, 2-hydroxy-1,10-phenanthroline is an important 2-position derivative of 1,10-phenanthroline derivatives, which can be synthesized through steps such as the reaction of phenanthroline with benzyl halides, oxidation of potassium ferrocyanide, and catalytic debenzylation of palladium on carbon, increasing the source pathway of the target product.
Candidate molecules for anticancer agents
1,10-Phenanthroline hydrate and its derivatives can serve as candidate molecules for anticancer agents. Research has shown that ligands formed by phenanthroline and copper ions exhibit DNA cleavage activity and can be used as non oxidative nucleic acid cleavage enzymes, thereby exhibiting certain anti-cancer activity. This anti-cancer mechanism may be related to the interaction between ligands and DNA, which inhibits the growth and reproduction of cancer cells by cleaving DNA. At present, research on the anti-cancer properties of ortho phenanthroline and its derivatives is still deepening, and it is expected to develop more effective anti-cancer drugs.
Metalloproteinase inhibitor
Phenanthroline is a non-specific inhibitor of metalloproteinases (MMPs) that can prevent streptozotocin-induced chromosomal aberrations. It can reduce the expression of MMP3 and MMP13 mRNA during the chondrogenic differentiation of human chondrocytes (hChs) and in explant models exposed to TNF α/IL-1 β. In addition, ortho phenanthroline (1mM) can also inhibit the autolysis of sea cucumber body walls. These studies indicate that ortho phenanthroline has a certain role in regulating the activity of metalloproteinases, which may provide new ideas for the treatment of related diseases.
Biomedical research field
Research on Iron Metabolism in Organisms
In the study of iron metabolism in living organisms, using ortho phenanthroline to detect the level of ferrous ions in cells or tissues can help to gain a deeper understanding of the mechanism of iron in physiological processes. Iron is involved in various important physiological processes in organisms, such as oxygen transport and energy metabolism. By accurately measuring the content of ferrous ions in cells or tissues, the processes of iron absorption, transportation, storage, and utilization can be studied, providing theoretical basis for the diagnosis and treatment of related diseases.
Research on DNA protein interaction
Phenanthroline can be used to study the interaction between DNA and proteins. When ortho phenanthroline complexes with copper, it exhibits nuclease activity and has been used to study DNA protein interactions. By studying the interaction between phenanthroline and DNA and proteins, we can understand the binding mode, binding strength, and the impact of the interaction on biological functions between DNA and proteins, providing important information for revealing the mysteries of life activities.
Electroplating additives
Phenanthroline can be used as an electroplating additive. Adding ortho phenanthroline during the electroplating process can improve the performance of the electroplating solution and enhance the quality of the electroplating layer. For example, it can adjust the dispersion and coverage ability of the plating solution, making the plating layer more uniform and dense; It can also improve the hardness and wear resistance of the electroplating layer, enhancing the service life of the electroplated product.
Animal fiber dye
Phenanthroline can also be used as a dye for animal fibers. It can undergo chemical reactions with animal fibers to form stable chemical bonds, thereby coloring the fibers. Phenanthroline dyes have the advantages of bright color and good color fastness, and have certain application value in the textile industry.
Manufacturing of environmental protection equipment
Phenanthroline materials have strong chemical stability and mechanical properties, and are widely used in the field of environmental protection. It can be used to manufacture components such as filters and sedimentation tanks in sewage treatment equipment, and its stability and corrosion resistance can extend the service life of the equipment. In addition, the high transparency of ortho phenanthroline materials can also help operators monitor the sewage treatment process and detect problems in a timely manner. In garbage disposal equipment, phenanthroline materials can be used to manufacture components such as filters and transportation pipelines. Compared with traditional materials, it has higher wear resistance and corrosion resistance, which can effectively reduce equipment maintenance and replacement costs. In the field of new energy, ortho phenanthroline materials can be used to manufacture outer coverings for solar panels to prevent erosion from rainwater and dust; 1,10-Phenanthroline hydrate can also be used to manufacture the cover layer of wind turbine blades to improve their durability and wind resistance performance.
1,10-Phenanthroline hydrate is a versatile compound with significant applications in analytical chemistry, catalysis, biochemistry, and industry. Its ability to form stable metal complexes makes it invaluable in various scientific and technological fields. However, its potential health and environmental risks necessitate strict safety measures and regulatory oversight. As research continues to uncover new applications and safer alternatives, the future of 1,10-Phenanthroline hydrate remains promising, provided that its use is managed responsibly to protect human health and the environment.
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