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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.
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.
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.
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
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.
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, 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.
Dye synthesis
Traditional reactive dyes mostly use cyanuric chloride as the connecting matrix of active groups, and the conjugated system of dye molecules is small, resulting in insufficient dye intensity. In order to achieve the specified dyeing depth, higher dye dosage is required, which exacerbates the problem of dye residue in dyeing wastewater. By using 2,4 quinolinediol as the chromophore of reactive dyes and utilizing its 2-position hydroxyl group, a new quinoline type reactive dye can be obtained by nucleophilic substitution reaction to introduce the cyanuric chloride active group.
The specific synthesis process is as follows: firstly, 2,4 quinolinediol is subjected to the first condensation reaction with cyanuric chloride in DMF solvent at low temperature conditions of 0-5 ℃, to obtain the quinoline intermediate substituted with the active group of monochlorotriazine; Subsequently, the intermediate was coupled with an aromatic amine diazonium salt to obtain a reactive dye containing a quinoline conjugated system. In the molecules of this new type of reactive dye, the conjugated system of quinoline ring forms an electronic synergistic effect with the active group, greatly improving the covalent bond stability between the dye and cellulose fibers.
The fixation rate on cotton fibers can reach over 90%, which is about 20% higher than traditional ordinary reactive dyes. At the same time, due to the higher molar extinction coefficient of dyes, the amount of dye used to achieve the same dyeing depth can be reduced by 25%, and the COD discharge of dyeing wastewater is significantly reduced, fully meeting the current clean production requirements of the printing and dyeing industry.
Synthesis of Dual Active Quinoline Reactive Dyes
In order to further improve the fixation rate of reactive dyes, the industry has developed dual active group reactive dye technology, and the dual active site characteristics of 2,4 quinolinediol provide a unique molecular basis for constructing new dual active group reactive dyes. By stepwise directional modification of the 2-position and 4-position hydroxyl groups of 2,4 quinolinediol, a new type of reactive dye containing two different types of reactive groups simultaneously on a single chromophore can be obtained by attaching a chlorotriazine active group and a vinyl sulfone sulfate active group to the same quinoline core.
The synthesis process of this dual active quinoline reactive dye has extremely high reaction selectivity: firstly, under low temperature and weak alkaline conditions, the 4-hydroxy group of 2,4 quinolinediol is coupled with the diazonium salt of the para ester to introduce the active precursor of ethylene sulfone sulfate ester; Subsequently, the system was heated to 40 ℃ and allowed to undergo a condensation reaction between the 2-position hydroxyl group and cyanuric chloride, followed by the incorporation of a chlorotriazine active group to ultimately obtain the target product.
In the dyeing process of cotton fibers, two different types of active groups of this dye can form covalent bonds with cellulose fibers under different temperature conditions. The dye's fixation rate can be increased to over 93%, and the wet friction color fastness of dyed fabrics can reach 4-5 levels, which is one level higher than traditional double active group active dyes. Currently, this type of dye has achieved industrial mass production in many large dye enterprises in Zhejiang and Jiangsu, becoming the main product for high-end cotton fabric dyeing.
Traditional reactive dyes in the continuous pad dyeing process of cotton fabrics face the problem of severe dye hydrolysis under high concentration alkaline fixation conditions, resulting in poor dyeing reproducibility and a large amount of unhydrolyzed dyes entering the wastewater, increasing the difficulty of treatment. The reactive dyes synthesized from 2,4 quinolinediol as the parent material have significantly improved alkali stability of the active groups in the dye molecules due to the strong electron deficient effect of quinoline heterocycles.
In a 20g/L caustic soda fixing bath, the hydrolysis rate of the dye is reduced by more than 60% compared to traditional benzene based reactive dyes. This highly alkali resistant quinoline reactive dye is perfectly adapted to the continuous pad dyeing process of cotton fabrics, greatly improving the production efficiency and one-time success rate of dyeing, and demonstrating strong application advantages on large-scale printing and dyeing production lines.
Fluorescent dyes are the core materials in the fields of biological labeling and fluorescence tracing. Traditional fluorescent dyes have the disadvantages of fast photobleaching speed and small Stokes shift, while quinoline fluorescent dyes synthesized from 2,4-dinitrophenyldiol exhibit extremely excellent fluorescence performance. By introducing different electron donating substituents at the 6th and 7th positions of 2,4-quinolinediol, the fluorescence emission wavelength of the dye can be precisely controlled, achieving full band fluorescence coverage from the blue to the red light region.
The typical synthesis process is to carry out a condensation reaction between 2,4-dichloroquinoline diol and p-dimethylaminobenzaldehyde under the catalytic conditions of concentrated sulfuric acid, to obtain a quinoline fluorescent dye with coumarin structure fusion. The fluorescence quantum yield of this dye can reach 0.72, with a Stokes shift of over 100nm, much higher than the traditional fluorescence dye's Stokes shift of around 20nm, completely avoiding the interference of excitation light on the detection signal during fluorescence detection.
At the same time, this type of quinoline fluorescent dye has extremely strong photostability. After continuous exposure to ultraviolet light for 2 hours, the retention rate of fluorescence intensity is still over 90%, which is more than 5 times that of traditional fluorescent dyes. At present, this type of fluorescent dye has been widely used in biomedical fields such as cell fluorescence labeling and immunofluorescence detection, becoming the core fluorescent material in high-end in vitro diagnostic reagents.
Synthesis of high-performance laser dyes
Laser dyes are the core working substances of dye lasers, requiring dyes to have extremely high photochemical stability, long fluorescence lifetime, and high laser conversion efficiency. The laser output wavelength range of traditional coumarin based laser dyes is narrow and lacks photostability, while quinoline based laser dyes synthesized with 2,4-dinitrophenyldiol as an intermediate perfectly compensate for these shortcomings.
The quinoline laser dye synthesized by modifying the molecular structure of 2,4 quinolinediol can achieve continuous tunable laser output in the 420-580nm wavelength range, with a laser conversion efficiency of over 30%, which is more than 10 percentage points higher than traditional coumarin laser dyes.At the same time, the photochemical stability of this type of quinoline laser dye is extremely excellent.
Under continuous pumping by a xenon lamp, the service life of the dye is more than four times that of traditional coumarin dyes. It has been widely used in industrial laser marking, medical laser beauty, spectral analysis instruments and other fields, becoming the core working medium of high-performance dye lasers.
In the field of ink and plastic coloring, traditional solvent dyes face the problems of low coloring power and poor migration resistance. However, solvent dyes synthesized from 2,4 quinolinediol as the parent material exhibit excellent organic solvent solubility and migration resistance due to their strong conjugated heterocyclic structure.The oil soluble azo quinoline dye obtained by coupling 2,4-dichloroquinoline diol with diazonium salts of long-chain alkyl aniline has extremely high solubility in organic solvents such as toluene and ethyl acetate, and its coloring power is more than 1.5 times that of traditional aniline solvent dyes.
The high-end plastic ink prepared with this type of dye has extremely bright printing patterns on PE and PP plastic films, with a color fastness to friction of level 5. At the same time, during the high-temperature injection molding process of plastics, the dye will not undergo thermal decomposition, migration, or exudation. The processing temperature tolerance range can reach over 300 ℃, and it has been widely used in the coloring field of food packaging plastics, fully meeting the safety standards for food contact materials.
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.
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