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2,4-Quinolinediol, molecular formula C9H7NO2, CAS 86-95-3, usually appears as a light brown powder. This compound has good solubility in organic solvents. This may be due to the presence of polar groups such as benzene rings and hydroxyl groups in its molecular structure, resulting in moderate intermolecular interactions and easy dispersion in organic solvents. However, the solubility in inorganic solvents such as water may be poor. Has high reactivity and can participate in various chemical reactions. For example, it can react with acids to generate corresponding salts; Under alkaline conditions, hydrolysis reactions can occur. These chemical reactions provide abundant possibilities for the synthesis, modification, and application of the compound.
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C.F |
C9H7NO2 |
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E.M |
161.05 |
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M.W |
161.16 |
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m/z |
161.05 (100.0%), 162.05 (9.7%) |
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E.A |
C, 67.08; H, 4.38; N, 8.69; O, 19.85 |
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Form |
powder |
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Color |
Very light brown |
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Melting point |
> 300 ° C (lit.) |
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Boiling point |
287.44°C (rough estimate) |
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Density |
1.2480 (Rough estimate) |
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Storage conditions |
Room Temp |
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Flash point |
> 230 ° F |
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Solubility H2O |
Insoluble in water |
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Refractive index |
1.5050 (Estimate) |
2,4-Quinolinediol, as an important organic compound, has shown wide application value in the field of chemical analysis, especially as a color developer or extractant for certain metal ions.
as a color developer
1. Detection and identification of metal ions
It can undergo complexation reactions with various metal ions to form complexes with specific colors. This color change can serve as an indicator signal for the presence or absence of metal ions. For example, if a specific color change is observed after adding the chemical to the solution, the presence of certain metal ions can be preliminarily determined. This color reaction is of great significance in the preliminary screening and qualitative analysis of metal ions.
2. Quantitative analysis of metal ions
In addition to serving as an indicator for qualitative analysis, it can also be used for quantitative analysis of metal ions. By comparing with a standard solution of metal ions of known concentration, a corresponding relationship between color depth and metal ion concentration can be established. By utilizing this relationship, quantitative analysis can be conducted on metal ion solutions of unknown concentrations to determine their concentration range. This method has the advantages of easy operation, fast and accurate, and is one of the commonly used methods in chemical analysis.
3. Separation and purification of metal ions
In some cases, it is necessary to separate and purify the metal ions in the mixed solution. Its color reaction can serve as an auxiliary means to help achieve this goal. By adjusting the pH value, temperature, and other conditions of the solution, the chelation equilibrium between metal ions can be altered, thereby achieving selective separation and purification of metal ions. This method has important application value in the extraction and purification process of metal ions.
as an extractant
1. Extracting metal ions from complex systems
In practical applications, metal ions often exist in complex systems such as soil, water, minerals, etc. The metal ions in these systems often coexist with various impurities, making it difficult to separate and extract them directly. 2,4-dihydroxyquinoline, as an effective extractant, can form stable complexes with metal ions, thereby achieving efficient extraction of metal ions from complex systems. This method has the advantages of easy operation, high extraction efficiency, and good selectivity, and is one of the commonly used methods in the field of metal ion extraction.
2. Optimize extraction conditions
In order to improve extraction efficiency, it is necessary to optimize the extraction conditions. This includes selecting appropriate extraction agent concentration, pH value, temperature and other parameters. For this compound, its extraction efficiency is influenced by various factors. By systematically studying the impact of these factors on extraction efficiency, optimized extraction conditions can be established to further improve extraction efficiency and selectivity.
3. Dynamics study during extraction process
During the extraction process, the complexation reaction between metal ions and them is an important kinetic process. By studying the rate constant, activation energy, and other parameters of this process, we can gain a deeper understanding of the mechanism and laws of the extraction process. This has important guiding significance for optimizing extraction conditions and improving extraction efficiency.
4. Synergistic effect with other extractants
In some cases, using it alone may not fully meet the extraction requirements. At this point, synergistic effects with other extractants can be considered to improve extraction efficiency and selectivity. For example, it can be mixed with other organic solvents or surfactants to form a composite extraction system. This composite extraction system often has higher extraction efficiency and better selectivity, which can meet more complex extraction requirements.
Specific application areas
Environmental monitoring
In the field of environmental monitoring, it can be used as a color developer or extractant to detect metal ion pollution in water bodies, soils, and other environments. By observing and analyzing its color changes or extraction efficiency, the content and distribution of metal ions in the environment can be preliminarily determined, providing strong support for environmental protection and governance.
Geological exploration
In the field of geological exploration, 2,4-Quinolinediol also has wide application value. It can be used as an extractant to extract metal ions from geological samples such as ores. By analyzing and comparing their extraction efficiency, the content and types of metal ions in the ore can be preliminarily determined, providing important reference for the development and utilization of mineral resources.
In the fields of medicine and biology
In the fields of medicine and biology, its color reaction and extraction performance have also attracted widespread attention. It can serve as an indicator or extractant for metal ions in living organisms, used to monitor the metabolism and distribution of metal ions in the body. This is of great significance for studying the functions and mechanisms of metal ions in living organisms.
How to Extract metal ions from geological samples
Extracting metal ions from geological samples such as ores involves a series of complex processes that require careful handling, precise chemical reactions, and advanced extraction techniques. Here's a concise overview of how this is typically done:
First, the ore sample is collected and thoroughly crushed and grinded into a fine powder to increase its surface area, facilitating more efficient extraction. This step is crucial as it ensures that the metal ions are more accessible for subsequent chemical treatments.
Next, the powdered sample undergoes a process called beneficiation, which involves separating the valuable minerals from the gangue (waste rock). This can be done through various methods such as magnetic separation, froth flotation, or gravity separation, depending on the physical and chemical properties of the minerals involved.
Once the valuable minerals are isolated, they are often subjected to leaching, a process where a suitable solvent or acid is used to dissolve the metal ions from the solid matrix. Common acids used in this step include sulfuric acid, hydrochloric acid, and nitric acid. The choice of acid depends on the nature of the ore and the metal being extracted.
The leachate, which now contains the dissolved metal ions, is then filtered to remove any solid residues. Subsequent steps may involve precipitation, where chemicals are added to cause the metal ions to precipitate out as solids, or ion exchange, where the metal ions are selectively adsorbed onto a resin or other sorbent material.
Finally, the metal ions are recovered from the precipitate or sorbent through processes such as electrolysis, smelting, or chemical reduction. These steps produce the pure metal or a metal compound that can be further processed into various products.
Throughout the entire extraction process, strict environmental and safety protocols are adhered to minimize pollution and ensure the health and safety of workers.
2,4-Quinolinediol, also known as 2,4-dihydroxyquinoline, is a chemical compound with the molecular formula C9H7NO2. It exists as a light brown powder and possesses distinct chemical properties.
This compound has a molecular weight of approximately 161.16 g/mol. Its boiling point is reported to be around 287.44°C to 388.44°C, depending on the experimental conditions, while the density is estimated to be in the range of 1.2480 to 1.376 g/cm³. The melting point is above 300°C.
In terms of its applications, it serves as a coupling component in the synthesis of yellow azo dyes and is also utilized as an intermediate in pharmaceutical syntheses. Additionally, it can be employed as a biochemical reagent for life science research, serving as a biomaterial or organic compound.
Handling this chemical requires caution due to its potential irritant properties. Appropriate safety measures, such as wearing protective clothing and ensuring adequate ventilation, should be taken when working with it to prevent any adverse effects on health.
In summary, 2,4-Quinolinediol is a versatile chemical compound with significant applications in dye synthesis, pharmaceutical intermediates, and biochemical research. Its distinct physical properties and chemical reactivity make it a valuable reagent in various scientific and industrial settings.
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2,4-Quinolinediol (2,4-dihydroxyquinoline) is a quinoline derivative with two hydroxyl substituents. Its chemical properties mainly manifest in aspects such as acidity, redox properties, solubility, thermal stability, reactivity, and safety. The following is a detailed elaboration of its chemical properties:
The 2,4-Quinolinediol molecule contains two hydroxyl groups (-OH), which can release hydrogen ions (H⁺), thus exhibiting certain acidity. Its acid dissociation constant (Pka) is approximately 4.50 ± 1.00 (predicted value), indicating that it can partially ionize in aqueous solution, generating the corresponding anion. This acidity enables 2,4-Quinolinediol to participate in acid-base reactions and undergo neutralization reactions with bases, generating salts and water.
The hydroxyl group in 2,4-Quinolinediol and the double bond on the quinoline ring give it certain redox properties. Under appropriate conditions, it can be oxidized by oxidants and undergo an oxidation reaction to form the corresponding oxidized product. At the same time, it can also be reduced under the action of reducing agents and undergo a reduction reaction. This redox property enables 2,4-Quinolinediol to have extensive applications in organic synthesis and can be used as an intermediate or catalyst in redox reactions.
2,4-Quinolinediol has poor solubility in water, but it has certain solubility in some organic solvents, such as dimethyl sulfoxide (DMSO), etc. This solubility enables it to react conveniently with other organic compounds in organic synthesis and drug preparation. At the same time, due to its poor solubility in water, it also has advantages in certain reactions where water avoidance is required.
2,4-Quinolinediol exhibits high thermal stability. Its melting point is greater than 300°C (as reported in the literature), and the predicted boiling point is around 400°C. This high thermal stability enables it to remain stable under high-temperature conditions and is less prone to decomposition or deterioration. Therefore, in organic synthesis reactions requiring high-temperature conditions, 2,4-Quinolinediol can be used as a stable reactant or catalyst.
The hydroxyl group in 2,4-Quinolinediol and the double bond on the quinoline ring give it high reactivity. It can react with various compounds, such as coupling with azo dyes to form corresponding azo compounds. This reactivity makes 2,4-Quinolinediol widely used in the dye industry. At the same time, it can also participate in other organic reactions, such as substitution reactions, addition reactions, etc.
2,4-Quinolinediol has a certain irritant property and may cause irritation to the skin and eyes. Therefore, appropriate protective measures need to be taken during the operation, such as wearing protective gloves and goggles. At the same time, it should be stored in a cool and ventilated warehouse to avoid contact with incompatible substances like oxidants.
Frequently Asked Questions
Is it called "diol" or "ketone"? Why are the names so confusing?
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Because it hardly exists in the form of "diol". Its IUPAC name is actually 4-hydroxy-1H-quinolin-2-one. In solution, it exists almost entirely in the form of a ketone (amide) structure, rather than an enol structure. The so-called '2,4-dihydroxyquinoline' is a structural misguidance - it is essentially a mixture of amide and enol.
How many "clones" can it transform into? Is the number of tautomers astonishing?
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There are up to 15 types of tautomers. This is due to the fact that its molecular skeleton can undergo proton transfer and double bond rearrangement, rapidly interconverting between various forms such as ketone, enol, and lactam imide. This' multiple personality 'makes it a popular model in molecular electronics and single-molecule device research.
Why do it have two "versions" of pKa and logP? Which one is trustworthy?
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It varies depending on the measurement conditions. The predicted pKa value is 4.50 ± 1.00, indicating that it is prone to protonation under acidic conditions; There are two types of logP: 0.7 (calculated) and 1.020 (estimated), indicating moderate lipophilicity. The differences between different databases stem from the calculation methods (XLogP3 vs fragmentation method) and whether or not to consider tautomeric balance.
Why do some MSDS say it is "suspected to cause genetic defects"? What should be noted during operation?
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Because it is labeled as H341 (suspected to cause genetic defects). Although the toxicity data is incomplete, Ames testing shows a risk of mutagenicity. Dust masks, goggles, and nitrile gloves must be worn during operation to avoid inhaling dust, and stored in an inert gas environment at 2-8 ° C.
Will it "transform" when combined with sodium ions? Any difference?
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It will become 2,4Quinolinediol monosodium salt (monosodium salt, CAS: 4510-76-3). After salt formation, the solubility significantly improved, and the molecular formula changed to C ₉ H ₆ NNaO ₂, with a molecular weight of 183.14 g/mol. This form is more commonly used in dye synthesis and biological research because it performs better in aqueous phase.
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