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What is the chemical structure of quinoline, 2- (4-bromophenyl) -?
Quinoline, 2 - (4 - bromophenyl), its chemical structure should be described according to chemical principles and structural rules. This compound is based on quinoline. Quinoline is a nitrogen-containing heterocyclic aromatic hydrocarbon with a phenyl ring and a pyridine ring structure. In quinoline position 2, it is connected with 4 - bromophenyl. In 4 - bromophenyl, it is a group with a bromine atom substituted at position 4 above the phenyl ring.
In this compound, the nitrogen atom of quinoline has a lone pair of electrons. In chemical reactions, it can be used as an electron donor to participate in coordination and other reactions. The conjugation of the benzene ring and the pyridine ring endows the molecule with certain stability and electron delocalization characteristics. However, 4-bromophenyl and bromine atoms have electronegativity, which can affect the electron cloud density of the benzene ring, making the electron cloud density of the adjacent and para-site of the benzene ring relatively decrease, and the meta-site relatively increase. This electronic effect affects the reactivity of electrophilic substitution and nucleophilic substitution of compounds.
Furthermore, in the spatial structure, the group connection of 2- (4-bromophenyl) quinoline may cause a certain spatial hindrance to the molecule, which affects the interaction and accumulation mode between molecules, and is reflected in the physical properties such as crystal structure and solubility. Therefore, the chemical structure of 2 - (4 -bromophenyl) quinoline is composed of the connection of the quinoline parent nucleus and 4 -bromophenyl group. Its electronic effect and spatial structure are intertwined, which together determine the chemical and physical properties of the compound.
Quinoline, 2- (4-bromophenyl) - What are the physical properties?
Quinoline, 2- (4-bromophenyl), this substance has many physical properties. Its properties are often crystalline, and it has a specific shape, such as whether the crystal form is regular or not, particle size thickness, etc. Color or colorless, or microstrip color, which is related to purity and impurities contained.
Melting point is a key physical constant, which is very important for identification and purification. Experimentally determined, the melting point of 2- (4-bromophenyl) quinoline is within a certain range, but it will fluctuate slightly due to measurement methods, instrument accuracy and sample purity.
Boiling point is also a significant characteristic, reflecting the equilibrium transformation conditions of the substance in the gas phase and the liquid phase. Under a specific pressure, its boiling point has a corresponding value, and when the pressure changes, the boiling point also changes.
Solubility is related to its dispersion in different solvents. In organic solvents, such as ethanol and ether, or show good solubility, molecules and solvent molecules interact through specific forces to disperse uniformly. However, in water, the solubility is poor, and it is difficult to overcome the molecular forces of water itself due to the interaction between molecular structure and water molecules.
Density, as an inherent property of substances, is closely related to molecular mass and molecular accumulation. Under specific temperature and pressure, the density of 2 - (4-bromophenyl) quinoline is a certain value, which has a great impact on its distribution and mixing in different media.
In addition, its refractive index is also an important optical property. When light passes through the material, the degree of refraction has a specific performance, which is related to the molecular structure of the material and the distribution of electron clouds. It is of great significance for optical research and related applications.
What are the synthesis methods of quinoline, 2- (4-bromophenyl) -?
The synthesis method of 2 - (4 - bromophenyl) quinoline is not described in the ancient book Tiangong Kaiwu, but according to the ancient chemical process principle and later organic synthesis methods, there may be the following ways.
First, 4 - bromobenzaldehyde and 2 - methylquinoline can be used as raw materials. First, 4 - bromobenzaldehyde is co-heated with the alkali solution, so that the aldehyde group undergoes hydroxyaldehyde condensation reaction. The aldehyde group is active. Under the catalysis of the base, the aldehyde group α - hydrogen dissociates to form a carbon negative ion, and then nucleophilic addition occurs with the methyl group of 2 - methylquinoline to form an intermediate product. After the dehydration step, the hydroxy group is dehydrated by acid or high temperature to form a carbon-carbon double bond, thereby building the basic skeleton of the target. This process requires precise control of the temperature and the ratio of reactants, and the concentration and dosage of alkali are also related to the reaction process. If the temperature is too high, the side reactions will increase; if the ratio is improper, the yield will decrease.
Second, aniline derivatives and halogenated aromatics are used as starting materials. First, aniline is protected by an acylation reaction to avoid overreaction in subsequent reactions. After that, it undergoes a Ullmann reaction with 4-bromohalobenzene, and under the action of metal catalysts such as copper or palladium, a carbon-nitrogen bond is formed to obtain a nitrogen-containing intermediate product. After cyclization, a suitable acid or Lewis acid is used as a catalyst to promote the formation of intramolecular rings to form a quinoline ring structure, and the final result is 2- (4-bromophenyl) quinoline. The key to this path lies in the activity and selectivity of the metal catalyst. If the activity is not good, the reaction will be slow or even not occur, and the selectivity is not good. And the introduction and removal of protective groups need to be mild to prevent damage to the target product.
Third, the Friedländer synthesis method can also be used. The reaction of 4-bromoacetophenone with o-aminobenzaldehyde in the presence of an acidic catalyst. The nucleophilic addition of the two first forms the Schiff base intermediate, and then the nucleophilic substitution in the molecule closes the loop, and then the oxidative dehydrogenation step can obtain the target product. This reaction requires quite high requirements for acidic catalysts, which can effectively catalyze the reaction without causing excessive decomposition of the reactants or products. During the reaction process, temperature and reaction time also need to be finely regulated to ensure yield and purity.
Quinoline, 2- (4-bromophenyl) - In what fields is it used?
Quinoline, 2 - (4 - bromophenyl), is useful in medicine, materials and other fields.
In the field of medicine, such compounds often have unique biological activities. Many studies have shown that those containing quinoline structure may have antibacterial, anti-inflammatory and anti-tumor effects. The structural characteristics of 2 - (4 - bromophenyl) quinoline may endow it with the power to bind to specific biological targets, such as specific proteins acting on some tumor cells. By inhibiting protein activity and hindering the proliferation of tumor cells, it is expected to become a lead compound for the development of new anti-tumor drugs. Or because its structure is compatible with key enzymes in bacteria, it can inhibit the growth and metabolism of bacteria and be used for antibacterial drug exploration.
In the field of materials, this compound also shows its ability. Due to its molecular structure containing a rigid quinoline ring and a bromophenyl group with specific electronic effects, it may participate in the construction of organic semiconductor materials. In organic Light Emitting Diode (OLED), or as a light-emitting layer material, it can achieve high-efficiency emission due to its specific electron transition characteristics. In solar cell materials, or by its light absorption and charge transport properties, it can improve the photoelectric conversion efficiency of batteries.
In addition, in the field of chemical synthesis, 2- (4-bromophenyl) quinoline can be used as a key intermediate. Due to the high reactivity of bromine atoms, it can be reacted with various organoboronic acids or olefins through the classical reactions of halogenated aromatics, such as Suzuki coupling, Heck reaction, etc., to introduce various functional groups or structural fragments, expand the organic synthesis route, and build more complex organic molecules with specific functions.
What is the market outlook for quinoline, 2- (4-bromophenyl) -?
2 - (4 - bromophenyl) quinoline, the situation of this substance in the city is as follows:
Looking at the city today, 2 - (4 - bromophenyl) quinoline is gradually emerging in the field of chemical raw materials and pharmaceutical intermediates. It is a key raw material in the organic synthesis industry. Due to the unique structure of quinoline, the substitution of 4 - bromophenyl gives it special chemical activity and can be used to construct a multi-component complex organic molecular structure.
In the field of pharmaceutical research and development, many researchers have noticed this compound. Geinoquinolines are often biologically active, and the introduction of 4-bromophenyl can optimize their pharmacological properties, such as enhancing their affinity for specific targets, so their potential value in the process of new drug creation has attracted much attention. However, because it is still in the research and promotion stage, the supply scale in the market is still limited compared with common bulk chemicals.
As far as production is concerned, some professional chemical companies have begun to explore the optimization of their synthesis processes. Strive to improve yield and reduce costs in order to gain a favorable position in future market competition. However, the synthesis process involves many fine steps and strict control of reaction conditions. Factors such as temperature and catalyst dosage have a profound impact on product purity and yield. Therefore, there are still very few people who can produce this product stably and with high quality at this stage.
At the end of the market demand, although it has not shown explosive growth, with the continuous deepening of pharmaceutical research and development and the increasing demand for novel structural raw materials in the field of organic synthesis, its market prospects are quite promising. Many pharmaceutical companies and scientific research institutions are increasingly demanding it, and often purchase it for experimental research to explore new paths for new drug research and development and new materials. Over time, if the synthesis process is mature and the cost is effectively controlled, the market share of 2- (4-bromophenyl) quinoline may increase significantly.