Cupferron is an organic compound, also known as N-phenyl-N-hydrogen peroxide (Phenylhydroxylamine peroxide). Which typically appears as white or creamy scaly crystals, which may darken over time due to slow decomposition. Despite this, it remains usable for analytical purposes. It has a melting point ranging from 150 to 155°C and a boiling point of 243.8°C at 760 mmHg. It is soluble in water and alcohol, making it convenient for use in aqueous solutions.
Its molecular structure contains N-hydromethylamide group and benzene ring group, with oxygen atoms on both sides. Soluble in hot water, ethanol, benzene and other organic solvents, and partially soluble in cold water at room temperature. The solubility in water is small, 0.04 grams can be dissolved per 100 milliliters of water. In addition, it can also form complexes with metal ions, such as Fe(III) and Cu(II). It is an organic peroxide with strong oxidation-reduction properties. In an acidic environment, it breaks down easily, releasing oxygen. In addition, it is also flammable and explosive, and must be stored in a cool, dry, and ventilated place. It is widely used in analytical chemistry and is often used in the colorimetric determination of copper ions, nickel ions, cobalt ions and iron ions. In addition, some of its derivatives can also be used in the preparation of semiconductor materials.
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Chemical Formula |
C6H9N3O2 |
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Exact Mass |
155 |
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Molecular Weight |
155 |
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m/z |
155 (100.0%), 156 (6.5%), 156 (1.1%) |
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Elemental Analysis |
C, 46.45; H, 5.85; N, 27.08; O, 20.62 |
Chemical Analysis
Metal Ion Detection: Commonly used as a chelating agent for the detection and determination of various metal ions, including aluminum, copper, iron, titanium, zirconium, and others. It forms stable complexes with these metals, allowing for their accurate quantification.
Separation and Precipitation: Can be used to separate copper and iron from other metal ions in solution. It is particularly effective in precipitating iron from strong acid solutions, making it a valuable tool in analytical chemistry.
Colorimetric Analysis: It is used in colorimetric methods for the determination of metals such as aluminum, bismuth, copper, iron, gallium, mercury, manganese, niobium, tin, tantalum, thorium, titanium, vanadium, and zirconium. The formation of colored complexes with these metals enables their quantitative analysis.
Final Solution
Vanadate Analysis
For the quantitative analysis of vanadate, forming a deep red precipitate that can be easily detected and measured.
Titanium Determination
It is also used for the quantitative determination of titanium, which forms a yellow precipitate when reacted with it.
Masking Agent
Acting as a masking agent in the analysis of rare earth elements, preventing interference from other metal ions.
Industrial Applications
Precipitant and Solvent Extractant
Cupferron is used as a precipitant and solvent extractant for metals such as copper, iron, tin, titanium, vanadium, and chromium. This makes it useful in processes where these metals need to be removed or concentrated from solutions.
Polymerization Inhibitor
Due to its unique polymerization-inhibiting properties, it can be used as an alternative to commonly used polymerization inhibitors like BHT (butylated hydroxytoluene). Its low required dosage makes it an economical choice for this application.
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Other applications
Organic synthesis
It can be used as reducing agent and oxidizing agent in organic synthesis. In organic synthesis reactions, the oxygen atoms of product can react with some compounds to generate corresponding carbonyl compounds. For example, It can oxidize benzaldehyde to benzoic acid, and in the presence of primary amines can convert halides to the corresponding primary amines. In addition, It can also be used as an antioxidant and electron acceptor for the preparation of semiconductor materials.
Drug research
It can be used for metal complex screening in pharmaceutical research. Since It can form a bright red complex, it can be used to detect whether the compound contains metal ions. Especially for some drug molecules containing transition metal ions, such as iron, copper, etc., It can be very helpful in the study of metal coordination effects in their pharmacological activity research and pharmacokinetics.
Environmental monitoring
It can be used for the analysis of organic pollutants in environmental monitoring. It has the ability to form complexes with certain organic pollutants, such as benzene, food additives, drugs, etc. These organic pollutants in the sample can be extracted by pre-treatment technology, and then react with It to form a color complex , thus convenient to quantify the analysis process. Therefore, It can be used for the detection of organic pollutants in water, soil and air.
Bioanalysis
It can be used for the detection of certain biomacromolecules in bioanalysis. For example, by interacting product with proteins, protein molecules can be changed, thereby realizing the separation of proteins and the detection of cellular components. In addition, It can also be used in DNA analysis, enzyme reaction, environmental monitoring and other research.
Spectral properties
The ultraviolet absorption peak of It is located between 250-300 nm, and the infrared spectrum shows characteristic peaks such as N-O stretching vibration, C-H stretching vibration, C-O stretching vibration and benzene ring stretching vibration.
It has multiple electronic structural units (such as benzene rings, urea functional groups, etc.), so its absorption spectrum characteristics are relatively complex. According to literature reports, It has a strong absorption band in the 250-300 nm region, which is mainly caused by the π-π* transition; there is also a weaker absorption band in the 300-400 nm region, located at about 324 nm, which may be caused by caused by n-π* transitions. In addition, in different polar solvents, the peak position and intensity of the absorption spectrum of It also changed. When ethanol is used as solvent, the maximum absorption peak of It is near 315 nm, in chloroform it is near 350 nm, in acetone it is about 310 nm.
As a multidentate ligand, It can form different complexes with transition metal ions, and its absorption spectrum changes accordingly. For example, in the presence of iron ions, It can form a chromogenic Fe(Cup)3 complex with a maximum absorption wavelength of around 530 nm. In addition, when It is used as a ligand to form a complex with a transition metal ion, the peak position and intensity of the absorption spectrum of the chromogenic complex will also change because the metal ion has an impact on the electronic structure of it.
Since It has a strong absorption spectrum after forming a complex with some transition metal ions, the content of different transition metal ions can be determined by spectrophotometry. Taking iron ion as an example, by reacting the sample to be tested with excess It, a colored Fe(Cup)3 complex can be formed, and then the absorbance value is measured with a spectrophotometer, and its concentration is calculated according to Beer's law. In addition to iron ions, It can also be used as a ligand in the spectrophotometric detection of metal ions such as manganese, cobalt, nickel, copper, and indium.
Cupferron, also known as N-Nitroso-N-phenylhydroxylamine ammonium salt, is a chemical compound with the CAS number 135-20-6. It is primarily used as an analytical reagent in various chemical and metallurgical applications. This compound is commonly referred to as "copper iron reagent" or "copper iron indicator" due to its specific reactivity with copper and iron ions.
One of the key properties is its ability to form insoluble complexes with metals such as copper, iron, aluminum, titanium, zirconium, and vanadium. These complexes can be extracted using organic solvents like chloroform or ethyl acetate, making it a valuable tool in the separation and analysis of these metals.
In analytical chemistry, it is employed for the quantitative determination of various metals including aluminum, bismuth, copper, iron, gallium, mercury, manganese, niobium, tin, tantalum, thorium, titanium, vanadium, and zirconium. It is particularly useful for the separation of copper and iron from other metal ions in strong acid solutions and as a masking agent for rare earth elements.
The compound's chemical formula is C6H9N3O2, and it has a molecular weight of 155.15 g/mol. The unique chelating properties allow it to coordinate through its oxygen atoms, making it an effective organic chelation reagent. Its reactivity can be influenced by factors such as pH and temperature of the solution.
When handling the compound, it is important to follow proper safety precautions due to its potential toxicity. It is classified as an acute toxic substance via oral ingestion and can cause skin and eye irritation. As such, it should be stored in a cool, dry place, preferably at temperatures between 2-8°C, and handled with appropriate personal protective equipment.
In summary, cupferron is a versatile chemical reagent widely used in analytical chemistry for the detection and quantification of various metals. Its ability to form stable complexes with specific metals and its solubility in common solvents make it an indispensable tool in metallurgical and chemical analyses.
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