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2-bromo-7-iodo-5h-pyrrolo chemical structure of [2,3-b] pyrazine
2-Bromo-7-iodo-5H-pyrrolo [2,3-b] pyrazine is an organic compound, and its chemical structure can be inferred by following the naming rules of organic chemistry.
"pyrrolo [2,3-b] pyrazine" indicates that the core structure of this compound is pyrrolido [2,3-b] pyrazine. The structure of pyrrolido pyrazine is formed by fusing pyrrole ring with pyrazine ring. Pyrrole ring is a five-membered heterocycle containing one nitrogen atom and is aromatic; pyrazine ring is a six-membered heterocycle containing two nitrogen atoms and is also aromatic. The two fused in a specific way to form this unique fused ring system.
"2-bromo-7-iodo" indicates the position and type of substituent on the core structure. "2-bromo" means that there is a bromine atom (Br) as a substituent at the position numbered 2 of the pyrrole [2,3-b] pyrazine structure; "7-iodo" means that there is an iodine atom (I) as a substituent at the position numbered 7.
In general, the chemical structure of 2-bromo-7-iodo-5H-pyrrolo [2,3-b] pyrazine is pyrrolido [2,3-b] pyrazine as the core, with bromine atoms at position 2 and iodine atoms at position 7. This structure endows the compound with unique physical and chemical properties, which may have potential application value in organic synthesis, medicinal chemistry and other fields.
What are the physical properties of 2-bromo-7-iodo-5h-pyrrolo [2,3-b] pyrazine
2-Bromo-7-iodo-5H-pyrrolo [2,3-b] pyrazine is an organic compound with unique physical properties. It is mostly solid at room temperature, and the molecules are arranged in an orderly manner due to strong intermolecular forces. The appearance of this compound is often off-white to light yellow crystalline powder, which is due to the absorption and reflection characteristics of molecular structure to light.
When it comes to melting point, the melting point of this compound is quite high, about 180-190 ° C. Due to the existence of strong intermolecular forces, such as hydrogen bonds, van der Waals forces, etc., more energy is required to make the molecules break free from the lattice and turn from solid to liquid.
In terms of solubility, it has a certain solubility in common organic solvents such as dichloromethane and N, N-dimethylformamide (DMF). In dichloromethane, because dichloromethane is a polar molecule, it interacts with some polar groups of the compound, which is conducive to its dissolution. However, in water, the solubility is extremely low, because the whole molecule is non-polar, it is difficult to form an effective interaction with water molecules, which violates the principle of "similar miscibility".
In addition, 2-bromo-7-iodo-5H-pyrrolo [2,3-b] pyrazine has certain stability, but its structure may change under specific conditions, such as high temperature, strong acid or strong alkali environment. Due to the high activity of bromine and iodine atoms in the molecule, substitution reactions can occur under appropriate reagents and conditions, thereby changing the properties and structures of the compounds.
What are the main uses of 2-bromo-7-iodo-5h-pyrrolo [2,3-b] pyrazine?
2-Bromo-7-iodo-5H-pyrrolo [2,3-b] pyrazine is a kind of organic compound. Its main use is more common in the field of organic synthesis.
In the field of organic synthesis, such nitrogen-containing heterocyclic compounds are often key intermediates. Its structure is unique, and the bromine and iodine atoms on the ring have high reactivity. Bromine atoms can introduce various functional groups to molecules through nucleophilic substitution reactions. If reacted with alcohols and amines, ether or amine-substituted derivatives can be formed, which is of great significance in the fields of medicinal chemistry and materials science.
Furthermore, iodine atoms have excellent performance in metal-catalyzed coupling reactions due to their large atomic radius and strong polarization. For example, in Suzuki coupling reaction and Stille coupling reaction, 2-bromo-7-iodo-5H-pyrrolo [2,3-b] pyrazine can be used as an important substrate to couple with borate esters or tin reagents to construct more complex organic molecular structures. This is an indispensable step in the construction of polycyclic aromatic hydrocarbon systems, the synthesis of materials with specific photoelectric properties, and the development of new drug molecules.
In the field of medicinal chemistry, nitrogen-containing heterocyclic structures often have good biological activity and pharmacokinetic properties. 2-Bromo-7-iodo-5H-pyrrolo [2,3-b] pyrazine as an intermediate, with subsequent modification, may be able to develop drugs targeting specific disease targets. For example, specific protein kinases of some tumor cells can be designed and synthesized as inhibitors, or this compound can be used as a starting material and gradually derived and optimized.
In materials science, by chemically modifying it to introduce a conjugated structure or a specific functional group, the electron cloud distribution and energy level structure of the molecule can be regulated, thereby endowing the material with unique photoelectric properties. For example, it can be used to prepare organic Light Emitting Diode (OLED) materials, or the luminous efficiency and stability of the device can be improved.
What are the synthesis methods of 2-bromo-7-iodo-5h-pyrrolo [2,3-b] pyrazine
To prepare 2-bromo-7-iodine-5H-pyrrolido [2,3-b] pyrazine, the following ancient method can be used.
First, choose a suitable starting material, such as a compound containing pyrrolido-pyrazine parent nucleus. The structure of the parent nucleus needs to be in line with the structure of the target product in order to lay the foundation for the subsequent reaction. However, the purity of the starting material must be excellent. If there are many impurities, it is easy to cause mistakes in the reaction and the product is impure.
After that, the steps of bromination are carried out. Often take suitable bromination reagents, such as liquid bromine, N-bromosuccinimide (NBS), etc. Taking NBS as an example, in an organic solvent, such as dichloromethane, under appropriate reaction conditions, such as adding the initiator benzoyl peroxide, and controlling the reaction temperature and time. The initiator can promote the generation of bromine radicals, and then substitution reaction with specific positions in the raw material, introducing bromine atoms at the second position of the pyrrole-pyrazine parent nucleus. In this step, the control of temperature is critical. If the temperature is too high, it is easy to cause excessive bromination and generate unnecessary polybrominated products; if the temperature is too low, the reaction rate will be slow and take a long time.
Then perform the iodization operation. Choose a suitable iodizing agent, such as potassium iodide in combination with an oxidizing agent, or directly use iodine elemental substance and appropriate additives. In the reaction system, by adjusting the reaction conditions, such as changing the solvent, pH, etc., the iodine atom selectively replaces the hydrogen atom of the 7-position parent nucleus. If potassium iodide and hydrogen peroxide are used as reagents, in specific solvents and buffer systems, hydrogen peroxide can oxidize potassium iodide to form active iodine species, and then achieve 7-position iodization.
After each step of the reaction, it needs to be separated and purified by fine separation and purification methods. Commonly used methods include column chromatography, recrystallization method, etc. Column chromatography can separate the product and impurities according to the difference in the polarity of the compound; recrystallization method uses the different solubility of the product and impurities at different temperatures to make the product pure. Only through these steps can 2-bromo-7-iodine-5H-pyrrolido [2,3-b] pyrazine be prepared. However, in the experimental operation, it is necessary to strictly follow the procedures and pay careful attention to the details of each reaction to obtain the desired results.
What are the characteristics of 2-bromo-7-iodo-5h-pyrrolo [2,3-b] pyrazine in chemical reactions
2-Bromo-7-iodo-5H-pyrrolo [2,3-b] pyrazine is an organic compound with many unique properties in chemical reactions.
Its structure contains a pyrrole-pyrazine core skeleton, which endows the compound with certain rigidity and conjugation properties. Bromine and iodine atoms are connected to specific positions, respectively, and the halogen atoms are active, resulting in significant reactivity of the compound.
In the nucleophilic substitution reaction, bromine and iodine atoms can be used as leaving groups. Due to the large iodine atom and relatively small C-I bond energy, iodine is easier to leave, and can be substituted with various nucleophiles, such as alkoxides, amines, etc., thereby introducing various functional groups to achieve structural modification and derivatization of compounds.
In the field of metal catalytic reactions, this compound can be used as a ligand or substrate. Its halogen atoms can participate in metal-catalyzed coupling reactions, such as Suzuki coupling, Stille coupling, etc. In these reactions, halogen atoms form intermediates with metal catalysts, and then couple with another organic fragment to construct complex organic molecular structures, which are widely used in drug synthesis, material chemistry and other fields.
Furthermore, due to the existence of conjugate structure, 2-bromo-7-iodo-5H-pyrrolo [2,3-b] pyrazine may have certain optical and electrical properties. During photochemical reactions or electron transfer processes, its structure and electron cloud distribution will change, affecting the reactivity and selectivity of compounds, providing potential application opportunities for photocatalytic reactions, photoelectric materials research and development, etc.
Due to its structural complexity and halogen atomic properties, careful operation is required in the selection and control of reaction conditions. It is necessary to ensure that the reaction is fully carried out, but also to avoid side reactions, such as excessive substitution, halogen atom elimination and other side reactions, which require harsh reaction conditions and require fine regulation of temperature, solvent, catalyst and other factors.