Name | 1-Benzothiophene |
Molecular Formula | C8H6S |
Molar Mass | 134.199 g/mol |
Appearance | Colorless to pale yellow solid |
Melting Point | 32 - 33 °C |
Boiling Point | 221 - 224 °C |
Density | 1.184 g/cm³ |
Solubility | Slightly soluble in water, soluble in organic solvents like ethanol, ether |
Flash Point | 94 °C |
Odor | Characteristic odor |
Cas Number | 95-15-8 |
Structure | A bicyclic compound with a benzene ring fused to a thiophene ring |
What are the main uses of Benzothiophene?
1-Benzothiophene is also an organic compound. It has a wide range of uses and is important in various fields.
First, in the field of medicinal chemistry, 1-benzothiophene is often a key structural unit. Many biologically active drug molecules contain this structure, so they can interact with specific targets in organisms to demonstrate pharmacological effects. For example, some anti-cancer drugs are cleverly designed to incorporate the structure of 1-benzothiophene, so that it can precisely act on cancer cells, or interfere with the metabolic process of cancer cells, or inhibit the proliferation of cancer cells, providing an effective way for the treatment of cancer.
Second, in the field of materials science, 1-benzothiophene also has outstanding performance. Due to its special electronic structure and physicochemical properties, it can be used to prepare organic optoelectronic materials. For example, polymers based on 1-benzothiophene have good photoelectric conversion properties, which can be applied to organic solar cells to improve the photoelectric conversion efficiency of batteries and contribute to the development of new energy materials. It can also be used as an organic Light Emitting Diode (OLED) material to endow OLED devices with unique luminous properties, such as higher luminous efficiency and better color purity, making display technology a new height.
Third, in organic synthetic chemistry, 1-benzothiophene, as an important synthetic intermediate, can be derived from complex and functional organic compounds through various chemical reactions. Chemists rely on their special chemical activities, such as substitution reactions and cyclization reactions, to build new organic molecular frameworks, greatly enriching the types of organic compounds, injecting vitality into the development of organic synthetic chemistry, promoting the field to continuously expand the boundaries and explore more unknown chemical spaces.
What are the physical properties of Benzothiophene?
1-Benzothiophene is a kind of organic compound. Its physical properties are particularly important, and it is related to its behavior in various chemical processes and applications.
First of all, under normal temperature and pressure, 1-benzothiophene is a colorless to light yellow oily liquid. Looking at its color and shape, this feature can help to identify and dispose of it in actual operation. It has a special smell, which is also part of its physical properties. Although it is difficult to describe it accurately in words, it is an important clue for identification in related experiments or industrial scenes.
times and melting point and boiling point. The melting point of 1-benzothiophene is about -29 ° C, and the boiling point is between 221-224 ° C. The melting point is quite low, so it is a liquid at room temperature; the boiling point indicates the energy required to convert it into a gaseous state. Knowing these two values is crucial in the separation and purification steps such as distillation and fractionation. It can be separated from other compounds according to its melting boiling point characteristics to obtain pure 1-benzothiophene.
Furthermore, the density of 1-benzothiophene is also an important property. Its density is about 1.14 g/cm ³, which is heavier than water. This property has a great impact on operations involving liquid-liquid separation. If it coexists with water in the system, due to its high density, it will sink underwater and can be separated by means of a liquid separation funnel.
In terms of solubility, 1-benzothiophene is insoluble in water, but soluble in organic solvents such as ethanol, ether, and benzene. This difference in solubility is due to the difference in its molecular structure and the force between water molecules and organic solvents. This property is widely used in organic synthesis and analytical chemistry. In organic synthesis, a suitable organic solvent is often selected to dissolve 1-benzothiophene, so that the reaction can proceed smoothly; in analytical chemistry, 1-benzothiophene can be extracted from the mixture for subsequent analysis and determination.
In addition, 1-benzothiophene is volatile to a certain extent. Although the volatility is not very significant, its volatilization cannot be ignored in an exposed system or high temperature environment. Be careful when operating, because volatilization is not only related to material loss, but also affects the accuracy of experimental results. In industrial production, it is more related to safety and environmental protection issues.
1-What are the chemical properties of Benzothiophene?
1-Benzothiophene is one of the organic compounds. Its structure contains a benzene ring fused with a thiophene ring. This compound has unique chemical properties and is widely used in many fields of organic synthesis and materials science.
1-Benzothiophene is a light yellow to white crystalline solid with a melting point of about 32-33 ° C and a boiling point of 221-224 ° C. Because of its conjugated system in the molecule, it has certain stability and aromaticity. Its aromaticity is derived from the conjugation of benzene and thiophene rings, giving it a special electron cloud distribution, which shows similar properties to typical aromatic compounds in chemical reactions.
In terms of chemical activity, the reactivity of 1-benzothiophene is mainly due to its conjugated system and the presence of heteroatom sulfur. Sulfur atoms can participate in a variety of reactions due to their lone pair electrons, such as nucleophilic substitution reactions, oxidation reactions, etc. In nucleophilic substitution reactions, the aromatic ring of 1-benzothiophene can be attacked by nucleophiles under specific conditions, resulting in the formation of substitution products. For example, in the presence of appropriate bases and solvents, halogenated 1-benzothiophene can react with nucleophilic reagents such as alkoxides and amines to generate corresponding substituted derivatives.
In the oxidation reaction, the sulfur atom of 1-benzothiophene is easily oxidized to form sulfoxide or sulfone compounds. This oxidation reaction often uses hydrogen peroxide, m-chloroperoxybenzoic acid, etc. as oxidants. The generated sulfoxide or sulfone derivatives can be used as intermediates in organic synthesis and participate in more complex reactions due to the change of the oxidation state of sulfur atoms.
In addition, 1-benzothiophene can also undergo electrophilic substitution reactions. Because the aromatic ring is rich in electrons, it is vulnerable to electrophilic attack. Common electrophilic substitution reactions include halogenation, nitrification, sulfonation, etc. In the halogenation reaction, 1-benzothiophene can be combined with halogens under the action of appropriate catalysts such as ferric chloride to form halogenated 1-benzothiophene.
In summary, 1-benzothiophene has become an important research object in the field of organic chemistry due to its unique structure, chemical properties and certain reactivity. It provides a key foundation for the development of new materials and the synthesis of complex organic molecules.
1-What are the synthesis methods of Benzothiophene?
1-Benzothiophene is also an organic compound. The synthesis method has been explored by many scholars in the past, but now it is the method of Jun Chen.
First, the method of using o-halogenated aryl mercaptan as raw material. First take o-halogenated aryl mercaptan, add an appropriate base, and in a suitable temperature and solvent to make it undergo an intramolecular cyclization reaction. For example, choose o-bromothiophenol, add potassium carbonate in N, N-dimethylformamide solvent, and heat it up to about 120 ° C. After several times of reaction, 1-benzothiophene can be obtained. This is because the base can capture the hydrogen of the o-halogenated aryl mercaptan, generate sulfur negative ions, and then attack the carbon connected to the halogen atom, forming a ring to obtain the target.
Second, through the decarboxylation of benzothiophene-2-carboxylic acid. First, benzothiophene-2-carboxylic acid is prepared, which can be obtained by a suitable reaction path. Then it is placed in a high temperature environment, often with copper salts as catalysts, so that it can undergo decarboxylation reaction. For example, at 250 ° C - 300 ° C, with copper carbonate as catalyst, benzothiophene-2-carboxylic acid decarboxylates and converts to 1-benzothiophene. Due to the synergy between high temperature and catalyst, the carboxyl groups are separated and the molecules are rearranged to obtain the product.
Third, the method of using aryl vinyl sulfide as raw material. Take aryl vinyl sulfide, use iodine as an initiator, and react in an organic solvent. If dichloromethane is used as a solvent and iodine is added to initiate, the double bonds in the aryl vinyl sulfide molecule interact with the sulfur atom, and the cyclization reaction generates 1-benzothiophene. This is the process of iodine promoting the cyclization of sulfur and double bonds.
All synthesis methods have their own advantages and disadvantages, depending on the ease of availability of raw materials, reaction conditions, product purity and many other factors, and choose the best one to use.
In which fields is Benzothiophene used?
1-Benzothiophene is one of the organic compounds and is useful in many fields.
In the field of pharmaceutical research and development, its function is particularly important. Chemists use 1-benzothiophene as a base to create various new drugs. Due to its special chemical structure, it can interact with specific targets in organisms. For example, compounds with specific biological activities can be designed to target the treatment of certain diseases. For example, for tumor diseases, modifying the structure of 1-benzothiophene or obtaining drugs with anti-tumor activity is expected to open up new avenues for the treatment of cancer.
In the field of materials science, 1-benzothiophene also plays a key role. It can be used to prepare optoelectronic materials. Due to its unique electronic properties, it can be integrated into the material system to improve the photoelectric properties of the material. For example, the introduction of 1-benzothiophene structural units in organic Light Emitting Diode (OLED) materials can improve the luminous efficiency and stability of the materials, so that the OLED display technology can be more perfect and achieve better display effect.
Furthermore, in the field of pesticides, 1-benzothiophene is also used. Using it as a raw material, pesticides with high insecticidal and bactericidal properties can be synthesized. Such pesticides can precisely act on the specific physiological processes of pests or pathogens, and are less toxic and environmentally friendly than traditional pesticides, which is of great significance for the sustainable development of agricultural production.
In addition, in organic synthetic chemistry, 1-benzothiophene is often used as a key intermediate. Chemists modify and derive its structure through various chemical reactions, thereby synthesizing organic compounds with more complex structures and more diverse functions, greatly enriching the variety of organic compounds and promoting the development of organic synthetic chemistry.