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What are the physical properties of 2-iodo-1-benzothiophene?
2-Iodine-1-benzothiophene is one of the organic compounds and is very important in the field of organic synthesis. Its physical properties can be described as follows:
Under normal temperature and pressure, 2-iodine-1-benzothiophene is often in a solid state or a crystalline state, which is caused by the intermolecular force. Its color is often white to light yellow. The formation of this color is related to the electron transition in the molecular structure.
When it comes to the melting point, the melting point of 2-iodine-1-benzothiophene is quite high, about [specific value] degrees Celsius. The higher the melting point, due to the strong interaction between molecules, such as van der Waals force 、π - π accumulation, etc. These effects make the molecules closely arranged, and more energy is required to cause the lattice to disintegrate and change from solid to liquid.
As for the boiling point, the boiling point is also higher, about [specific value] degrees Celsius. The high boiling point is due to the strong intermolecular forces. In order to get the molecules out of the liquid phase and become gas phase, a large amount of energy needs to be supplied to overcome these forces.
In terms of solubility, 2-iodine-1-benzothiophene has different solubility in organic solvents. It has good solubility in common organic solvents such as dichloromethane, chloroform, and tetrahydrofuran. Because the molecular structure of the compound has a certain hydrophobicity, it can form a similar miscibility with the molecules of organic solvents. However, in water, its solubility is very small, and it is difficult to form an effective interaction with water molecules due to its non-hydrophilic molecular structure. For the density of
, the density of 2-iodine-1-benzothiophene is greater than that of water, which is related to its molecular composition and structure. The relative atomic mass of the iodine atom in the molecule is large, resulting in an increase in its unit volume mass, so the density is greater than that of water.
In summary, the physical properties of 2-iodine-1-benzothiophene, such as its properties, melting point, boiling point, solubility and density, are determined by its molecular structure and composition. These properties are of great significance for the selection of separation, purification and reaction conditions in organic synthesis and related studies.
What are the chemical properties of 2-iodo-1-benzothiophene?
2-Iodine-1-benzothiophene is also an organic compound. Its chemical properties are specific and worth exploring.
In terms of reactivity, the halogen atomic activity of halogenated aromatic hydrocarbons is often the key to chemical reactions. The iodine atom in 2-iodine-1-benzothiophene is active and easily involved in nucleophilic substitution reactions. The cover iodine atom has a large radius, the C-I bond energy is relatively low, and it is easy to break. Nucleophilic reagents can attack it to generate new compounds. For example, when reacting with sodium alcohol, the iodine atom can be substituted with an alkoxy group to form ether derivatives. This reaction is commonly used in the organic synthesis of ether compounds containing benzothiophene structure.
Furthermore, the conjugated system with aromatic hydrocarbons can undergo electrophilic substitution reaction. The electron cloud density distribution of benzothiophene ring is different, and the specific position is attractive to electrophilic reagents. Usually, the electron cloud density of the α position of the thiophene ring is relatively high, and electrophilic substitution is easy to occur here. In case of halogenated reagents, the α position of the thiophene ring or the pre-halogenation form polyhalogenated benzothiophene derivatives. This reaction can enrich the structure of benzothiophene compounds and lay the foundation for the subsequent synthesis of products with diverse functional groups.
In addition, 2-iodine-1-benzothiophene can also participate in metal catalytic coupling reactions. In the presence of metal catalysts such as palladium and nickel, it reacts with boric acid or borate esters containing alkenyl and aryl groups to realize the construction of carbon-carbon bonds. This reaction has a wide range of uses in the construction of complex organic molecular frameworks, the creation of bioactive compounds and functional materials.
Its stability also needs attention. Although the conjugate system increases its stability, the iodine atom is active. Under specific conditions, such as high temperature, strong base or strong oxidant environment, the compound may decompose or react unexpectedly. Therefore, when storing and using, it is advisable to avoid such extreme conditions and keep its chemical structure intact.
In conclusion, 2-iodine-1-benzothiophene is an important intermediate in the field of organic synthesis due to its rich chemical properties of iodine atom and benzothiophene ring, and has broad application prospects.
What are the common synthetic methods of 2-iodo-1-benzothiophene?
2-Iodine-1-benzothiophene is an important intermediate in organic synthesis. Its common synthesis methods are roughly the following numbers.
First, 1-benzothiophene is used as the starting material and obtained by halogenation reaction. The halogenating reagents commonly used here include iodine and an appropriate oxidizing agent. In an appropriate solvent, such as dichloromethane, chloroform and other inert organic solvents, add 1-benzothiophene, and then slowly add iodine elements and oxidizing agents, such as hydrogen peroxide, potassium persulfate, etc. When reacting, pay attention to the control of temperature. Generally, the reaction can proceed smoothly between low temperature and room temperature. Because the thiophene ring of 1-benzothiophene has a certain electron cloud density, under suitable conditions, the iodine atom can be selectively substituted in the 2-position, which is based on the law of its electron cloud distribution and reactivity.
Second, synthesized by metal-catalyzed coupling reaction. First prepare the halogenate (non-iodized) containing the benzothiophene skeleton, such as 2-bromo-1-benzothiophene, and then select a suitable metal catalyst, such as palladium catalyst (such as tetra (triphenylphosphine) palladium, etc.), with appropriate ligands, and couple with iodizing reagents (such as potassium iodide, etc.) under basic conditions. In this reaction system, the choice of solvent is also very critical. The commonly used organic solvents are N, N-dimethylformamide, dioxane, etc. The alkaline environment can be provided by bases such as potassium carbonate and sodium carbonate. The metal catalyst can activate the carbon-halogen bond of halogenated benzothiophene, making it easy to couple with the iodine source to generate 2-iodine-1-benzothiophene.
Third, the strategy of introducing iodine atoms while constructing benzothiophene rings. For example, using o-halogenated thiophenol and halogenated acrylate as raw materials, under basic conditions, a cyclization reaction occurs first to construct a benzothiophene ring, and the halogen atom of the halogenated acrylate can be replaced by an iodine atom at a suitable reaction check point in the subsequent reaction step. At the beginning of the reaction, the base can promote a series of reactions such as nucleophilic substitution between o-halogenated thiophenol and halogenated acrylate, and then close the ring to form a benzothiophene skeleton. Then, through a suitable iodine substitution agent, the iodine substitution process is completed under appropriate conditions, and the final result is 2-iodine-1-benzothioph
2-iodo-1-benzothiophene in what areas
2-Iodo-1-benzothiophene is an important intermediate in organic synthesis and has applications in many fields.
In the field of medicinal chemistry, its application is quite extensive. Due to its unique structure, a variety of compounds can be chemically modified. In many drug development, 2-iodo-1-benzothiophene is used as the starting material, and molecules with specific biological activities can be prepared through a series of reactions. For example, some small molecule drugs targeting specific disease targets, 2-iodo-1-benzothiophene participates in the construction of the skeleton, which plays a key role in the combination of drugs and targets, providing the possibility for the development of new therapeutic drugs.
It is also seen in the field of materials science. In the preparation of organic optoelectronic materials, 2-iodo-1-benzothiophene can introduce specific functional groups to change the electrical and optical properties of the materials. Through rational design and synthesis, excellent Light Emitting Diode materials, solar cell materials, etc. can be prepared. Due to its unique electronic structure and iodine atomic properties, it can regulate the charge transport and luminous efficiency of materials, and improve the performance of materials in optoelectronic devices.
In addition, in the field of pesticide chemistry, 2-iodo-1-benzothiophene also has potential applications. It can be used as an intermediate in the synthesis of new pesticides, and compounds with high insecticidal, bactericidal or herbicidal activities can be designed and synthesized. By modifying its structure, the selectivity and affinity of the compound to different targets can be adjusted, and the development environment-friendly, efficient and low-toxicity pesticide products can be realized.
In organic synthetic chemistry, 2-iodo-1-benzothiophene is a commonly used intermediate. Its iodine atom has high reactivity and can participate in a variety of classical organic reactions, such as Suzuki coupling reaction, Stille coupling reaction, etc. Through such reactions, carbon-carbon bonds and carbon-heteroatom bonds can be conveniently constructed to realize the construction of complex organic molecules, providing a powerful tool for organic synthetic chemists to help synthesize organic compounds with diverse structures.
What are the precautions in the preparation of 2-iodo-1-benzothiophene?
When preparing 2-iodine-1-benzothiophene, there are several issues that need to be paid attention to.
The choice of starting materials is crucial. The purity and quality of the raw materials are directly related to the quality and quantity of the product. High purity benzothiophene should be selected. If there are few impurities, there will be few side reactions and the product will be easy to purify.
The control of reaction conditions should not be underestimated. In terms of temperature, this preparation reaction often needs to be carried out within a specific temperature range. If the temperature is too low, the reaction rate will be slow and take a long time; if the temperature is too high, it may cause frequent side reactions and damage the purity of the product. For example, in some reactions, precise temperature control between 50 and 60 degrees Celsius can make the reaction smooth and efficient.
Furthermore, the choice of iodine substitutes is also critical. Different iodine substitutes have different activities and selectivity. Common examples include iodine elemental substance, N-iodine succinimide (NIS), etc. Although iodine elemental substance has low cost, it has high activity and poor selectivity; NIS activity is relatively mild and the selectivity is often better. It can be selected according to the specific reaction requirements.
The reaction solvent also has a great influence on the reaction. It is necessary to choose a solvent with good solubility to the reactants and products and no adverse interference to the reaction. For example, dichloromethane, N, N-dimethylformamide (DMF) are all commonly used solvents, but the reaction rate and product distribution in different solvents may be different, so careful consideration should be given.
In addition, the monitoring of the reaction process is indispensable. The reaction process can be monitored in real time by means of thin layer chromatography (TLC) and gas chromatography (GC). Observe the consumption of raw materials and the generation of products, and adjust the reaction conditions in a timely manner to prevent excessive or insufficient reaction.
Post-treatment steps cannot be ignored. When separating and purifying the product, extraction, column chromatography and other methods are commonly used. During extraction, select the appropriate extractant to ensure the effective transfer of the product; during column chromatography, select the appropriate stationary phase and eluent to obtain high-purity products.
All of these are important items to be paid attention to when preparing 2-iodine-1-benzothiophene, so that high-quality products are expected.
