Name | 8 - Hydroquinoline |
Molecular Formula | C9H9N |
Molar Mass | 131.175 g/mol |
Appearance | Solid |
Color | Light yellow to brown |
Melting Point | 45 - 47 °C |
Boiling Point | 267 - 268 °C |
Solubility | Slightly soluble in water, soluble in organic solvents |
Density | 1.059 g/cm³ |
Flash Point | 116 °C |
Odor | Characteristic odor |
What is the chemical structure of 8-Hydroquinoline?
8-Hydroxyquinoline is also an organic compound. Its molecular structure is unique, which is composed of a quinoline ring and a hydroxyl group. The quinoline ring is a nitrogen-containing heterocyclic aromatic hydrocarbon, which has the shape of a benzene ring and a pyridine ring, and is aromatic. At the 8 position of the quinoline ring, the hydroxyl group (-OH) is connected to it.
In this structure, the quinoline ring endows the 8-hydroxyquinoline conjugate system, which makes the electron cloud distribution unique and has specific chemical activity. The presence of hydroxyl groups also significantly affects its properties. Hydroxyl groups are strong electron-giving groups, and through its p-π conjugation effect, the electron cloud density on the benzene ring and the pyridine ring can be increased, especially the ortho and para-sites. This electronic effect changes the electrophilic substitution activity of 8-hydroxyquinoline, and the hydroxyl group can participate in many chemical reactions, such as esterification and etherification.
And because of the interaction between the quinoline ring and the hydroxyl group, 8-hydroxyquinoline can exhibit special coordination properties and can form stable complexes with various metal ions. This property makes it widely used in analytical chemistry, materials science and other fields. Its structural properties are the foundation of its chemical properties and applications, and are the key to its research and application.
What are the main physical properties of 8-Hydroquinoline?
8-Hydroxyquinoline is a kind of organic compound. It has many important physical properties.
Looking at its appearance, it is white to light yellow crystalline powder at room temperature, just like a delicate frost powder, fine and uniform. This form makes it easy to handle in many operations and applications.
When it comes to the melting point, the melting point is about 75-76 ° C, and the boiling point is 267 ° C. The lower melting point causes it to melt into a liquid state at relatively mild temperatures. This characteristic is convenient for it to mix evenly with other substances and participate in the reaction in some processes that require heat treatment. The higher boiling point indicates that it has good stability in conventional environments and is not easily vaporized and dissipated due to temperature fluctuations.
Solubility is also a key property. 8-Hydroxyquinoline is slightly soluble in water, but soluble in ethanol, ether, chloroform and other organic solvents. This difference in solubility makes it unique in different solvent systems. It is difficult to dissolve in the aqueous phase, but it can be well dissolved in organic solvents. This characteristic makes it play an important role in separation, purification and specific organic synthesis reactions. According to its solubility difference, the experimental process can be skillfully designed to achieve effective separation from other substances or participate in specific reaction paths.
Its density is about 1.312g/cm ³, which gives it a specific sedimentation or dispersion behavior in various systems, and has a profound impact on density-related operations such as liquid-liquid extraction, phase separation and other processes.
In addition, 8-hydroxyquinoline also has sublimation properties, which can be directly converted from solid state to gaseous state under specific conditions. This property provides another way for its purification and some special applications.
In summary, the physical properties of 8-hydroxyquinoline are interrelated, which together determine its application and value in many fields such as chemical industry, medicine, and materials.
Where is 8-Hydroquinoline used?
8-Hydroxyquinoline has a wide range of uses and is useful in many fields.
First, in the field of medicine, it shows unique ability. Antibacterial and antifungal drugs can be prepared. Because it can complex with metal ions in microorganisms, interfere with the metabolic process of microorganisms, and then inhibit their growth and reproduction. In the past, doctors used to treat diseases and often looked for things that could control bacteria. 8-Hydroxyquinoline has just this property and can be used to deal with certain infections.
Second, it is also an important agent in the field of analytical chemistry. It can be used as a metal ion precipitator and a complexing agent. Complexes formed by different metal ions and 8-Hydroxyquinoline have their own characteristics, so that metal ions can be separated and identified. The ancient chemical analysis, but there is no accurate method, 8-hydroxyquinoline came out, making the analysis of metal ions more accurate.
Third, in the field of materials science, it also has extraordinary performance. Can be used to prepare luminescent materials, semiconductor materials, etc. In the manufacture of optoelectronic equipment, the auxiliary material obtains specific optical and electrical properties. With the development of science and technology, the demand for optoelectronic equipment is increasing, and 8-hydroxyquinoline plays an important role in this.
Fourth, in agriculture, it also contributes. It can be used as a plant growth regulator to regulate plant growth and development, help it thrive, and increase crop yield. In ancient agriculture, I often worried about poor crop growth, and 8-hydroxyquinoline can relieve farmers' worries.
It can be seen that 8-hydroxyquinoline is indispensable in the fields of medicine, analytical chemistry, materials science, agriculture, etc., and is a substance with a wide range of functions.
What are the synthesis methods of 8-Hydroquinoline?
8-Hydroxyquinoline is also an organic compound, which is widely used in the fields of chemical industry, medicine and materials. Although the ancient people did not involve this method of synthesis, there are many scholars today who have explored it. It is briefly described as follows:
First, the Skraup synthesis method. This is a classic method, which involves the co-thermal reaction of o-aminophenol, glycerol, concentrated sulfuric acid and weak oxidants such as nitrobenzene. Glycerol is dehydrated by concentrated sulfuric acid to form acrylic aldehyde, which is combined with o-aminophenol for nucleophilic addition, and then cyclized and oxidized to obtain 8-hydroxyquinoline. In this process, concentrated sulfuric acid is not only a dehydrating agent, but also participates in the reaction. Nitrobenzene has the effect of oxidation, so that the intermediate product is oxidized to the target However, the reaction conditions of this method are harsh, high temperature is required, and nitrobenzene is highly toxic, which is unfavorable to the environment.
Second, Doebner-von Miller synthesis method. Aniline and glycerol are used as raw materials and react in the presence of concentrated sulfuric acid and catalyst. First, glycerol is dehydrated to acaldehyde, condensed with aniline, and then cyclized to obtain 8-hydroxyquinoline. This method is milder than the Skraup method, but concentrated sulfuric acid is still used to corrode equipment, and product separation is also inconvenient.
Third, the synthesis method of quinoline as raw material. Quinoline can be obtained by oxidation, substitution and other series of reactions. For example, quinoline is first oxidized to quinoline-N-oxide, and then reacted with nucleophiles to introduce hydroxyl groups at position 8. This approach is a bit complicated, but the raw material quinoline is easily available, and some reaction conditions are mild, which may have advantages for specific needs.
Fourth, electrochemical synthesis method. In recent years, an emerging method involves redox reaction on the surface of the electrode to prepare 8-hydroxyquinoline. This method is green and environmentally friendly, the reaction conditions are mild, and it can be precisely controlled. However, the technology is not mature, and industrial application still needs time.
What are the precautions for using 8-Hydroquinoline?
8-Hydroxyquinoline is a chemical substance, and many matters need to be paid attention to during use.
First, it is related to safety protection. This substance has certain toxicity and irritation, and it is necessary to wear suitable protective equipment when coming into contact. For example, wear protective gloves to prevent it from directly touching the skin, causing skin damage, redness, swelling, itching, etc.; wear goggles to avoid it accidentally splashing into the eyes and damaging the eyes. And the operation should be carried out in a well-ventilated place. If conditions permit, it is best to operate in a fume hood to prevent inhalation of its volatile gas and damage to the respiratory tract.
Second, about storage methods. 8-Hydroxyquinoline should be stored in a cool, dry and ventilated place, away from fire and heat sources. Due to its nature or affected by environmental factors, improper storage or deterioration will affect the use effect. At the same time, it should be stored separately from oxidants, acids, etc. to prevent mutual reaction and cause danger.
Third, it involves usage specifications. Before use, be sure to know its chemical properties and related reaction mechanisms, and precisely control the dosage. When conducting chemical reactions, strictly follow the experimental procedures or production processes, and do not change the reaction conditions at will, so as not to affect the reaction results or even cause safety accidents. After use, the remaining substances and waste should be properly disposed of and should not be discarded at will. They should be disposed of in accordance with relevant environmental protection regulations to prevent environmental pollution. In short, when using 8-hydroxyquinoline, safety is paramount and operation is standardized, so as to ensure the safety of personnel and the smooth progress of work.