What are the chemical properties of 3-Cyanoquinoline?

3-Cyanoquinoline is an important compound in organic chemistry. Its chemical properties are unique and contain many wonders.

Looking at its structure, the quinoline ring is connected to the cyanyl group, which gives it special activity. Cyanyl is a strong electron-absorbing group, which causes uneven distribution of molecular electron clouds and decreases the density of electron clouds on the quinoline ring. This property makes 3-cyanoquinoline exhibit different reactivity and selectivity from ordinary quinoline in the electrophilic substitution reaction.

In the nucleophilic substitution reaction, the presence of cyanide can activate the quinoline ring and attract nucleophilic reagents to attack. Due to the strong electron-absorbing effect of the cyanyl group, some positions on the ring are more susceptible to attack by nucleophiles, and then the substitution reaction occurs to form various derivatives.

In addition, 3-cyanoquinoline also has certain reaction characteristics in the redox reaction. The cyanyl group can participate in the redox process, or be reduced under specific conditions to form other functional groups such as amino groups, thereby expanding its application in the field of organic synthesis.

In terms of stability, the cyano group forms a conjugated system with the quinoline ring, which enhances the molecular stability to a certain extent. However, under extreme conditions such as high temperature, strong acid or strong base, its structure may also change, leading to the hydrolysis of cyano groups or other reactions on the ring. The chemical properties of 3-cyanoquinoline are rich and diverse, and it has important research and application value in the fields of organic synthesis and medicinal chemistry, providing a broad space for chemists to create novel compounds and explore new reaction mechanisms.

What are the common synthesis methods of 3-Cyanoquinoline?

The common synthesis methods of 3-cyanoquinoline generally include the following.

One is obtained by cyanidation with quinoline as the starting material. Among them, halogenated quinoline and cyanide reagents, such as potassium cyanide, sodium cyanide, etc., are often used to carry out nucleophilic substitution reactions under appropriate catalysts and reaction conditions. The catalyst can be a copper salt such as cuprous cyanide. In heating and an inert gas-protected atmosphere, the halogen atom is replaced by a cyano group to obtain 3-cyanoquinoline. The reaction mechanism is that the nucleophilic reagent attacks the carbon site of the halogen atom of halogenated quinoline, and the halogen ion leaves to form the target product.

Second, it can be synthesized by cyclization of compounds containing nitrogen heterocycles and cyanyl groups. For example, with appropriate aniline derivatives and cyanyl-containing α, β-unsaturated carbonyl compounds, under the catalysis of acid or base, Michael addition reaction occurs first, followed by intramolecular cyclization, to construct a quinoline ring and introduce a cyanide group. If a base is used as a catalyst, the base first captures the active hydrogen of the aniline derivative, forms a nucleophile, attacks the β-carbon of α, β-unsaturated carbonyl compounds, and then undergoes a ring-closing reaction within the molecule, eventually generating 3-cyanoquinoline.

Furthermore, cross-coupling reactions catalyzed by transition metals can also be achieved. The cross-coupling of haloquinoline with cyanyl sources, such as organozinc cyanide and organoboron cyanide, occurs under the action of transition metal catalysts such as palladium catalysts. The palladium catalyst is first oxidized with haloquinoline, then metallized with the cyanyl source, and finally reduced and eliminated to form a carbon-cyanide bond to obtain 3-cyanoquinoline. This method is relatively mild in conditions and has good selectivity, and is quite commonly used in organic synthesis.

3-Cyanoquinoline is used in what fields

3-Cyanoquinoline is useful in the fields of medicine and materials.

In the field of medicine, it is often a key intermediate for the creation of new drugs. Due to the diverse biological activities of the quinoline structure, adding cyanyl groups can significantly change the electron cloud distribution and spatial configuration of the compound, thereby improving the affinity and selectivity to specific biological targets. For example, in the research and development of many anti-cancer drugs, 3-cyanoquinoline-derived compounds can inhibit the proliferation of cancer cells or interfere with the metabolic pathways of cancer cells to achieve the purpose of anti-cancer.

In the field of materials, it also has important value. In the field of organic optoelectronic materials, 3-cyanoquinoline can affect the photoelectric properties of materials due to its unique electronic structure. Introducing it into the organic Light Emitting Diode (OLED) material system may improve the luminous efficiency and stability of materials. And in the field of fluorescent sensing materials, 3-cyanoquinoline can use its fluorescence properties to perform highly sensitive detection of specific ions or molecules. When encountering a target, its fluorescence intensity, wavelength and other properties change, which can achieve accurate detection of harmful substances in the environment or specific markers in organisms.

In summary, 3-cyanoquinoline is an indispensable and important substance in the fields of medicine and materials, and has made outstanding contributions to the progress of related technologies.

What is the market price of 3-Cyanoquinoline?

I don't know the market price of 3-Cyanoquinoline. This compound may vary widely in price due to its use, purity, and supply and demand. In the chemical raw material market, its price may be influenced by a variety of reasons.

If it is used in the pharmaceutical field, it requires high purity, complex production processes, and high prices. Pharmaceutical needs often require high purity levels, impurities must be strictly controlled, and the production process involves multiple purification and refining processes. The cost increases and the price rises.

If it is used in scientific research experiments, although the amount used is small, the quality and stability requirements are high, and the price is not low. Scientific research uses focus on batch stability and data reproducibility. Production needs to be precisely controlled, costs are increased, and market pricing is also high.

If the large-scale industrial production field, such as organic synthesis intermediates, the amount of consumption is large, if the production technology is mature and the output is high, the unit cost may drop due to the scale effect, and the market price may be relatively easy.

However, the market supply and demand relationship is also critical. If there is a sudden increase in demand, the supply will be difficult for a while, and the price will rise; if the supply exceeds the demand, the manufacturer will sell the goods, or reduce the price. In addition, the fluctuation of raw material prices, the improvement of production processes, and the impact of policies and regulations will all change the market price of 3-Cyanoquinoline. To know the exact price, you must consult chemical product suppliers, traders, or check the chemical product price information platform to get the current more accurate price.

What are the physical properties of 3-Cyanoquinoline?

3-Cyanoquinoline is one of the organic compounds. Its physical properties are particularly important, related to its performance in various chemical processes and practical applications.

First of all, its appearance, under room temperature and pressure, 3-cyanoquinoline is mostly white to light yellow crystalline powder, which is easy to observe and operate. Its yellowish color reflects the distribution of electron clouds in its molecular structure and the characteristics of conjugated systems.

As for the melting point, it is between 146-148 ° C. The melting point is the characteristic constant of the substance, and this value indicates the strength of the intermolecular force of 3-cyanoquinoline. When the temperature rises to the melting point, the molecule is energized enough to overcome the lattice energy and changes from solid to liquid state. This phase transition process is of great significance in the fields of material processing and purification.

In terms of solubility, 3-cyanoquinoline is insoluble in water. Because water is a polar solvent, while 3-cyanoquinoline molecules have weak polarity, according to the principle of "similar compatibility", the two are incompatible. However, it is soluble in organic solvents such as ethanol, chloroform, and dichloromethane. The polarity of organic solvents such as ethanol is compatible with 3-cyanoquinoline molecules, and interactions such as van der Waals forces can be formed between molecules, thus causing them to dissolve. This solubility property provides a basis for the selection of suitable reaction media and product separation in organic synthesis.

In addition, 3-cyanoquinoline has certain stability. Under conventional conditions, the molecular structure is relatively stable, and it is not easy to decompose or other chemical reactions spontaneously. In case of extreme conditions such as high temperature and strong oxidants, its stability may be damaged, and the molecular structure will change, causing chemical changes. This stability feature needs to be paid attention to during storage and transportation, and it is necessary to ensure that the environment is suitable to ensure its quality.

In summary, the physical properties of 3-cyanoquinoline, such as appearance, melting point, solubility and stability, each have their own chemical significance, which lays the foundation for its application in chemical research, industrial production and related fields.