4-(4-Nitrophenyl)azoresorcinol, also known as 4-(4-nitrophenyl)-1,2-dihydroxybenzene, is a synthetic organic compound belonging to the class of azoarenes. It is characterized by the presence of a nitrophenyl group attached to the 4-position of a resorcinol (1,3-dihydroxybenzene) moiety through an azo (-N=N-) linkage. This unique structure endows the molecule with distinct chemical and physical properties.
The nitro group (-NO2) in it contributes to its polarity, solubility in polar solvents, and its potential as an electron acceptor in chemical reactions. The azo bond, on the other hand, is known for its stability and can participate in various organic transformations, including reduction, oxidation, and substitution reactions.
This compound finds applications in various fields, including as a dye intermediate, a precursor for the synthesis of more complex organic molecules, and potentially in the development of functional materials due to its unique electronic and optical properties. Additionally, its structural features make it an interesting subject for research in organic chemistry, particularly in the areas of azo chemistry and heterocyclic synthesis.
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Chemical Formula |
C12H9N3O4 |
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Exact Mass |
259.06 |
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Molecular Weight |
259.22 |
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m/z |
259.06 (100.0%), 260.06 (13.0%), 260.06 (1.1%) |
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Elemental Analysis |
C, 55.60; H, 3.50; N, 16.21; O, 24.69 |
Chemical Reagent For Magnesium Determination
Sensitivity and Accuracy: It serves as a highly sensitive reagent for the determination of magnesium ions in various chemical and biological samples. This makes it an essential tool in analytical chemistry, particularly for quantitative analysis.
Non-Aqueous Titration Indicator: Additionally, 4-(4-Nitrophenyl)azoresorcinol functions as an indicator in non-aqueous titration processes, enhancing the precision and accuracy of such measurements.
Adsorption Indicator
Visual Indicator: It acts as an adsorption indicator, allowing for the visual detection of changes in adsorption processes, which are crucial in a range of analytical and preparative techniques.
Versatility: Its use as an adsorption indicator underscores its broad applicability in fields where the monitoring of adsorption phenomena is essential.
Magnesium Detection in Biological Systems
As a reagent for magnesium detection, it can be used to quantify magnesium levels in biological samples such as serum, plasma, or tissue extracts. Magnesium is an essential mineral for many biological processes, including nerve function, muscle contraction, and energy production, making its accurate quantification crucial in biomedical research and clinical diagnostics.
Role in Analytical Techniques
The compound's use as an indicator in titrations and other analytical procedures can facilitate the development of more sensitive and selective assays for the detection and quantification of various analytes in biological samples. This can be particularly important in the fields of pharmacology, toxicology, and environmental monitoring.
Potential for Novel Applications
Recent research has focused on the development of photochromic liquid crystal compounds, including those derived from azo compounds like 4-(4-Nitrophenyl)azresorcinol. These materials have unique properties that make them attractive for applications in information storage, optical switches, and sensors. While these applications are primarily based on their physical and optical properties, their potential integration into biological systems or devices for biomedical purposes is an area of ongoing research.
The chemical formula of even oxygen violet is C12H9N3O4, with a molecular weight of 259.22 and a melting point typically between 195-200 º C. The preparation process usually involves the reaction of p-nitroaniline and 1,3-phenyldiol. Specifically, a certain amount of p-nitroaniline is dissolved in hot concentrated hydrochloric acid, cooled, and then a saturated aqueous solution containing nitrous acid is added dropwise to generate diazonium salts. Then react this diazonium salt solution with 1,3-phenylenediol and dilute alkaline solution to obtain even oxygen violet. After filtration, drying, and alcohol recrystallization, this 4-(4-Nitrophenyl)azoresorcinol can be obtained with high purity.
Main purpose
1. Sensitive reagent for measuring magnesium
As a sensitive reagent, it is widely used for the determination of magnesium. In chemical analysis, it can form specific complexes with magnesium ions, and the content of magnesium in the sample can be accurately and quickly detected through methods such as color change or spectral measurement. This method is not only highly sensitive but also easy to operate, making it widely used in fields such as geological exploration, environmental monitoring, and food analysis.
2. Non aqueous titration indicator
It also plays an important role in non-aqueous titration. During the titration process, it can be used as an indicator to indicate the endpoint of titration through color changes. Due to its obvious color change and easy observation, it improves the accuracy and efficiency of titration. In addition, it has good solubility and stability in certain specific non-aqueous solvents, making it an indispensable indicator in non-aqueous titration.
3. Preparation of Azobenzene Photochromic Liquid Crystal Compounds
It can also be used to prepare an azobenzene photochromic liquid crystal compound. This compound undergoes reversible cis trans isomerization under light irradiation, exhibiting photochromic properties. At the same time, it also has liquid crystal properties, which makes it have potential application value in the field of information storage. Azobenzene based liquid crystals have received widespread attention and research in recent years due to their unique photo induced cis trans isomeric properties. As one of the important raw materials for preparing such liquid crystal compounds, it provides strong support for the development of optical storage, optical holography technology, and optical information processing.
4. Other potential applications
In addition to the main uses mentioned above, it may also have other potential application values. For example, due to its excellent optical performance and thermal stability, it may be used in fields such as optical materials and thermosensitive materials. In addition, with the continuous development of science and technology, people will continue to explore the application possibilities of even oxygen violet in more fields.
Application examples and case analysis
1. Application in magnesium determination
In geological exploration, magnesium content is one of the important indicators for measuring the quality of rocks and ores. By using it as a sensitive reagent for measuring magnesium, the magnesium content in rocks and ores can be quickly and accurately detected. For example, in a geological exploration, researchers collected multiple rock samples and measured the magnesium content in the samples using reagents. The results indicate significant differences in magnesium content among different rock samples, providing strong data support for subsequent geological analysis and resource assessment.
2. Application in Non aqueous Solution Titration
In non-aqueous titration, it is also widely used as an indicator. For example, in drug analysis, certain drug components have high solubility in non-aqueous solvents, so non-aqueous titration is required for determination. At this point, it can serve as an indicator to indicate the endpoint of titration through color changes. In a drug analysis, researchers used it as an indicator to successfully determine the content of drug components in non-aqueous solvents, providing strong support for drug quality control.
3. Application in the preparation of photochromic liquid crystal compounds
It also plays an important role in the preparation of azobenzene photochromic liquid crystal compounds. For example, in a certain study, researchers successfully synthesized a liquid crystal compound with photochromic properties using it as one of the raw materials. This compound can undergo reversible cis trans isomeric changes under light irradiation, resulting in significant color changes. This discovery provides new ideas and methods for the development of fields such as optical storage, optical holography technology, and optical information processing.
As an organic compound, even oxygen violet has wide application value in fields such as chemical analysis and material preparation. Its application as a sensitive reagent for determining magnesium and a non-aqueous titration indicator has been widely recognized and applied; Meanwhile, great potential has been demonstrated in the preparation of azobenzene photochromic liquid crystal compounds. However, attention should also be paid to its safety and environmental issues during use. In the future, with the continuous development of science and technology, the application fields will become more extensive, and it is also necessary to continuously improve its production process and performance to adapt to new demands and challenges.
Safety and Environmental Considerations
► Toxicity
4-(4 - Nitrophenyl)azoresorcinol, like many azo compounds, may have potential toxic effects. The nitro group and the azo group are considered to be potentially hazardous functional groups. Inhalation or ingestion of the compound can cause irritation to the respiratory and digestive systems. Skin contact may also lead to allergic reactions or irritation. Long - term exposure to high concentrations of the compound may have more serious health effects, such as damage to the liver or kidneys. Therefore, appropriate safety measures, such as wearing protective clothing and using proper ventilation, should be taken when handling this compound.
► Environmental Impact
The production and disposal of 4-(4 - nitrophenyl)azoresorcinol can have an impact on the environment. The synthesis process may involve the use of hazardous chemicals and generate waste products that need to be properly treated to prevent environmental pollution. If the compound is released into water bodies, it may have adverse effects on aquatic life, as some azo compounds are known to be toxic to fish and other organisms. Sustainable production methods and proper waste management strategies should be adopted to minimize the environmental impact of this compound.
► Degradation and Biodegradability
The degradation of 4-(4 - nitrophenyl)azoresorcinol in the environment is an important consideration. The nitro group and the azo group can be resistant to biodegradation, which means that the compound may persist in the environment for a long time. However, under certain conditions, such as in the presence of specific microorganisms or under photochemical irradiation, the compound may undergo degradation. Understanding the degradation pathways and factors affecting the biodegradability of 4-(4 - nitrophenyl)azoresorcinol is crucial for assessing its environmental fate and developing strategies for its safe disposal.
In the history of chemical development, the discovery of many compounds often stems from accidental observations and unexpected results. The discovery process of 4- (4-nitrophenyl) azoresorcinol (commonly known as magnesium reagent I) is a typical case, spanning multiple fields from dye chemistry to analytical chemistry, demonstrating an interesting trajectory of scientific discovery.
In the mid-19th century, dye chemistry ushered in its golden age. In 1856, young British chemist William Henry Perkin accidentally discovered the first synthetic dye, aniline violet, while attempting to synthesize the antimalarial drug quinine. This accidental discovery not only ushered in a new era of synthetic dyes, but also laid the foundation for the subsequent discovery of azo dyes.
German chemist Johann Peter Gries systematically discovered the diazotization reaction in 1858. This breakthrough discovery provides a theoretical basis for the synthesis of azo compounds.
During the dye development boom of the late 19th and early 20th centuries, chemists synthesized thousands of azo compounds. As a diazo component, p-nitroaniline has attracted much attention due to its strong electron withdrawing properties; Resorcinol is often chosen as a coupling component due to its high reactivity. The coupling reaction between the two mainly generates 4- (4-nitrophenyl) azoresorcinol, and a small amount of isomers coupled at the 2-position are also generated.
In the early 20th century, with the development of the Industrial Revolution, analytical chemistry faced new challenges. Traditional inorganic qualitative analysis methods, such as system analysis relying on hydrogen sulfide, are cumbersome to operate and highly toxic. Chemists began to seek simpler and more sensitive organic reagents for the detection and identification of metal ions.
In the 1920s, some sharp analytical chemists re examined the azo compounds that were "eliminated" in dye screening. They found that 4- (4-nitrophenyl) azoresorcinol can undergo a unique color change with magnesium ions in alkaline media: from the red or purple color of the reagent itself to a vivid blue color. This discovery immediately caught the attention of the analytical chemistry community.
German analytical chemist Hermann Beck first systematically studied this phenomenon around 1925. He found that the blue complex formed between the reagent and magnesium ions in sodium hydroxide medium has high sensitivity, with a detection limit of up to ppm. Baker's research laid a theoretical foundation for the application of this reagent in magnesium detection.
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