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What is the chemistry of 2-bromo-4-iodopyridine?
2-Bromo-4-iodopyridine is an organic compound whose molecules contain specific positions of bromine (Br) and iodine (I) substituted pyridine rings. This compound has unique chemical properties and has attracted much attention in the field of organic synthesis.
From the perspective of reactivity, both bromine and iodine atoms of 2-bromo-4-iodopyridine have nucleophilic substitution reactivity. Because the electronegativity of the halogen atom is larger than that of carbon, the carbon-halogen bond is polar, and the carbon atom is partially positively charged and vulnerable to attack by nucleophiles. And the pyridine ring has electron deficiency, which further enhances the activity of the carbon-halogen bond. Usually, iodine atoms are more likely to leave than bromine atoms due to their large atomic radius and relatively small C-I bond energy, and iodine atoms are preferentially replaced in nucleophilic substitution reactions. For example, when reacting with sodium alcohol, iodine atoms can be replaced by alkoxy groups to form corresponding ether derivatives.
2-bromo-4-iodopyridine can also participate in metal catalytic coupling reactions. Under the catalysis of transition metals such as palladium and nickel, it can cross-couple with carbon-containing nucleophiles to form carbon-carbon bonds. For example, the Suzuki coupling reaction with aryl boronic acid can form biaryl compounds containing pyridine structures. This reaction is of great significance in the fields of drug synthesis and materials science, and can effectively construct complex organic molecular structures.
In addition, because the pyridine cyclic nitrogen atom has lone pairs of electrons, it can coordinate with metal ions, and 2-bromo-4-iodopyridine can be used as a ligand to participate in the synthesis of metal-organic complexes. The formed complexes may have special catalytic properties and optical properties, and show application potential in catalysis, luminescent materials and other fields. < Br >
2-bromo-4-iodopyridine is rich in chemical properties and has important application value in organic synthesis, medicinal chemistry, materials science and other fields. It is a key intermediate for the preparation of various functional organic compounds.
What are the common synthetic methods of 2-bromo-4-iodopyridine?
2-Bromo-4-iodopyridine is an important intermediate in organic synthesis. Its common synthesis methods are as follows:
One is halogenation. Pyridine is used as the starting material and is prepared by halogenation reaction. Pyridine and brominating reagents, such as bromine ($Br_2 $), can undergo electrophilic substitution in the presence of appropriate catalysts to introduce bromine atoms into the pyridine ring. Due to the electronic effect of the nitrogen atom in the pyridine ring, the reaction mainly occurs at the β position (ie, the 3rd and 5th positions) of the pyridine ring, so the reaction conditions need to be carefully regulated to promote the selective introduction of bromine atoms to the 2nd position. Commonly used catalysts are Lewis acids, such as aluminum trichloride ($AlCl_3 $), iron tribromide ($FeBr_3 $), etc. When bromine atoms are successfully introduced, iodine atoms are introduced through iodine substitution reaction. Iodine sources, such as iodine elemental ($I_2 $), can be used with suitable oxidants, such as hydrogen peroxide ($H_2O_2 $) or nitric acid ($HNO_3 $), etc., under appropriate conditions, to introduce iodine atoms to the 4 position.
The second is metal catalytic coupling method. Pyridine derivatives containing specific substituents are prepared first, and then metal catalytic coupling reactions are used to construct target molecules. For example, 2-bromopyridine is used as a raw material and reacts with an organolithium reagent or Grignard reagent to form a corresponding metal-organic intermediate. This intermediate reacts with an iodine substitution reagent to introduce iodine atoms at the 4th position. Commonly used metal catalysts include palladium ($Pd $), nickel ($Ni $), etc. This method has the advantages of mild reaction conditions and high selectivity.
The third is a conversion method starting from other pyridine derivatives. If the starting material is a pyridine derivative with a suitable functional group, 2-bromo-4-iodopyridine can be synthesized by functional group conversion. For example, pyridine derivatives with suitable substituents gradually convert functional groups into bromine and iodine atoms through a series of reactions such as oxidation, reduction, and halogenation, so as to obtain the target product.
When synthesizing 2-bromo-4-iodopyridine, the appropriate synthesis method should be carefully selected according to the availability of starting materials, the difficulty of reaction conditions, and the purity requirements of the target product.
2-bromo-4-iodopyridine in what areas?
2-Bromo-4-iodopyridine is an important intermediate commonly used in organic synthesis and has been widely used in many fields.
In the field of medicinal chemistry, it plays a key role. It is used as the starting material for the construction of many drug molecules. Due to its pyridine ring structure and the existence of bromine and iodine atoms, it endows the compound with unique reactivity and spatial structure. It can be connected with other active groups through various chemical reactions, such as nucleophilic substitution, coupling reactions, etc., to construct a complex molecular structure with specific biological activities. Taking the development of anti-cancer drugs as an example, researchers can introduce specific pharmacoactive groups through 2-bromo-4-iodopyridine, modify the molecules to enhance their targeting and inhibitory activity against cancer cells, and help create new anti-cancer drugs.
In the field of materials science, it is also indispensable. In the preparation of organic optoelectronic materials, this compound can be used to participate in polymerization reactions to prepare polymer materials with special optoelectronic properties. Because bromine and iodine atoms can adjust the electron cloud distribution and energy level structure of the material, the resulting material exhibits excellent photoelectric conversion efficiency and stability in Light Emitting Diode, solar cells and other devices, providing the possibility for the development of high-performance organic optoelectronic devices.
In the field of pesticide chemistry, 2-bromo-4-iodopyridine also plays an important role. It can be used as a key intermediate for the synthesis of new pesticide active ingredients. Through rational molecular design and reaction, it can be converted into pesticide compounds with high efficiency to kill or inhibit specific pests or pathogens, and because of its unique structure, it may endow pesticides with better environmental compatibility and selectivity, reducing the impact on non-target organisms.
What are the physical properties of 2-bromo-4-iodopyridine?
2-Bromo-4-iodopyridine is an organic compound with unique physical properties. Looking at its properties, it is mostly in a solid state under normal conditions, and the molecules are arranged in an orderly manner due to the intermolecular force. Its melting and boiling point also has characteristics. Because the molecule contains bromine and iodine atoms, the atomic weight is large and the intermolecular force is enhanced, the melting point is relatively high, and a certain amount of heat is required to break the intermolecular binding and melt; the boiling point is not low, and gasification requires more energy to overcome the intermolecular attractive force.
In terms of solubility, the compound has a certain solubility in organic solvents such as dichloromethane and chloroform. Due to the principle of "similar miscibility", the organic structure and the organic solvent molecules can form van der Waals forces to promote dissolution. However, because it contains polar bromine and iodine atoms, the solubility in water is not good. Water is a strong polar solvent, and the interaction between the molecules of this compound is weak, making it difficult to disperse it in water.
The color state of 2-bromo-4-iodopyridine is often white to light yellow, which is caused by the light absorption and reflection characteristics of the molecular structure. Its density is higher than that of water, and the weight of the bromine and iodine atoms in the molecule is large, which increases the unit volume mass. In addition, the compound has certain stability, but under specific conditions, such as high temperature, strong acid and base, or when there is a specific catalyst, its bromine and iodine atoms can undergo substitution and other reactions. Due to the activity of halogen atoms, the molecule has a reactive activity check point.
What is the market price of 2-bromo-4-iodopyridine?
2-Bromo-4-iodopyridine is a fine chemical commonly used in the field of organic synthesis. Its market price often fluctuates due to a variety of factors.
First of all, the cost of raw materials for preparing this compound has a significant impact on the price. The prices of raw materials such as bromide, iodide and pyridine derivatives vary depending on market supply and demand, and origin. If the supply of raw materials is short, the price will rise, which will push the price of 2-bromo-4-iodopyridine up.
Furthermore, the complexity of the synthesis process also affects the price. The synthesis of this compound may require a multi-step reaction, involving special reaction conditions and catalysts. Complex and high-cost processes, such as the use of expensive catalysts or the need for harsh reaction environments, can increase production costs and prices.
Market supply and demand is a key factor. If there is strong demand for this compound in fields such as medicine and materials science, but the supply is limited, the price will rise. Conversely, if demand is weak and the supply is excessive, the price will fall.
In addition, the scale of production also has an impact. Large-scale production has reduced unit production costs due to scale effects, and the price may be more affordable; small-scale production has higher costs and relatively expensive prices.
According to past market conditions, the price of 2-bromo-4-iodopyridine per gram may range from tens to hundreds of yuan. However, it should be made clear that this price is only an approximate range, and the actual price fluctuates in real time according to the above factors. If purchasers want to know the exact price, they should consult the chemical product supplier in detail to obtain the latest quotation.