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What are the main uses of 4-Fluorobenzenesulfonyl Chloride?
4-Fluorobenzenesulfonyl chloride has a wide range of uses in the field of organic synthesis. It can be used as a key reagent to prepare a variety of compounds containing sulfonyl groups.
First, it can react with alcohols to obtain sulfonate esters. In this reaction, the sulfonyl chloride group of 4-fluorobenzenesulfonyl chloride (-SO ² Cl) and the hydroxyl group of alcohol (-OH) undergo nucleophilic substitution. Sulfonate is often used as an excellent leaving group in organic synthesis, which is helpful for subsequent reactions, such as nucleophilic substitution and elimination reactions, etc., to facilitate the construction of complex organic molecular structures.
Second, it interacts with amine compounds to form sulfonamides. Sulfonamides are widely used in the fields of medicine and pesticides, and some of them have biological activities such as antibacterial, anti-inflammatory, and weeding. By reacting 4-fluorobenzenesulfonyl chloride with different structural amines, sulfonamides with diverse structures can be prepared, expanding the possibility of their research and development in biologically active substances.
Third, under certain specific conditions, 4-fluorobenzenesulfonyl chloride can participate in the construction of heterocyclic compounds. Heterocyclic compounds are widely found in natural products and drug molecules. The reaction of 4-fluorobenzenesulfonyl chloride provides an effective path for the synthesis of such biologically active heterocyclic structures and enriches the synthesis strategy of heterocyclic compounds. Fourth, in the field of materials science, the sulfonyl-containing polymers it participates in the synthesis may have special physical and chemical properties, such as good solubility and thermal stability, which can be applied to coatings, plastics and other materials to endow materials with new properties.
What are the physical properties of 4-Fluorobenzenesulfonyl Chloride?
4-Fluorobenzenesulfonyl chloride is a commonly used reagent in organic synthesis. Its physical properties are as follows:
Looking at its shape, it is mostly a colorless to light yellow liquid at room temperature, with a clear appearance and a certain fluidity. Its odor is often pungent, which is caused by its high chemical activity.
When it comes to the boiling point, it is about 255-257 ° C. This boiling point value indicates that it can transform into a gaseous state at higher temperatures, showing relatively high thermal stability. The melting point is about 15 ° C, which means that when the temperature drops to this value, this state will gradually change from liquid to solid.
In terms of density, it is about 1.528g/cm ³, which is higher than the density of water, so it will sink at the bottom in water.
In terms of solubility, 4-fluorobenzenesulfonyl chloride is insoluble in water, which is caused by the hydrophobic benzene ring and sulfonyl chloride group in its molecular structure. However, it is soluble in common organic solvents such as ether, dichloromethane, and chloroform. In the organic synthesis reaction environment, it can well miscible with many organic reagents, providing convenient conditions for the smooth progress of various reactions.
In addition, its volatility is relatively low, and under normal environmental conditions, it is less lost quickly due to volatilization. However, due to its strong corrosiveness and irritation, it is necessary to use extra caution and take proper protective measures to prevent harm to the human body and the surrounding environment.
4-Fluorobenzenesulfonyl the chemistry of Chloride
4-Fluorobenzenesulfonyl chloride is an important reagent in organic synthesis. It has active chemical properties, which are due to the characteristics of sulfonyl chloride (-SO 2O Cl) and fluorine atoms (-F).
Looking at its sulfonyl chloride group, this structure is very active. It is easy to hydrolyze in contact with water. During hydrolysis, the chlorine atom in the sulfonyl chloride group is replaced by a hydroxyl group (-OH), resulting in 4-fluorobenzenesulfonic acid and hydrogen chloride. The hydrolysis reaction is violent and often releases a lot of heat. This process requires caution.
Furthermore, 4-fluorobenzenesulfonyl chloride can react with alcohols to form sulfonates. In organic synthesis, this reaction is often used to prepare sulfonate compounds with specific structures. During the reaction, the chlorine atom in the sulfonyl chloride group leaves and combines with the hydrogen atom of the alcohol hydroxyl group to form hydrogen chloride, while the sulfonyl group is connected with the hydrocarbon group of the alcohol to form a sulfonate ester.
Before amine compounds, 4-fluorobenzene sulfonyl chloride can also show its activity and react with it to form sulfonamides. This reaction is an important path for the construction of sulfonamide structures and is widely used in pharmaceutical chemistry and materials science.
The presence of fluorine atoms also has a significant impact on its chemical properties. Fluorine atoms are highly electronegative and have a strong electron-absorbing effect. This effect decreases the electron cloud density of the benzene ring, which in turn affects the electrophilic substitution reaction activity on the benzene ring, making the density of the adjacent and para-position electron clouds lower than that of the meta-position, resulting in electrophilic reagents more prone to attack the meta-position.
At the same time, due to the small radius of fluorine atoms and the large carbon-fluorine bond energy, fluorine-containing compounds usually have high stability and unique physical and chemical properties. In some reactions, the products formed by 4-fluorobenzenesulfonyl chloride exhibit special biological activity and thermal stability due to the characteristics of fluorine atoms.
In conclusion, 4-fluorobenzenesulfonyl chloride plays a key role in many fields of organic synthesis due to its unique structure, chemical activity, and diversity. However, when operating, it is necessary to fully consider the risks and precautions caused by its activity characteristics.
What is the preparation method of 4-Fluorobenzenesulfonyl Chloride?
4-Fluorobenzenesulfonyl chloride is a commonly used reagent in organic synthesis. Its preparation method, although the ancient book "Tiangong Kaiwu" does not detail the preparation of such fine chemicals, it can be referred to today's chemical process method.
One method is to use 4-fluorobenzenesulfonic acid as the starting material to react with chlorination reagents. Commonly used chlorination reagents include phosphorus pentachloride. Place 4-fluorobenzenesulfonic acid in a suitable reaction vessel and slowly add phosphorus pentachloride under the protection of inert gas. When the two meet, a chemical reaction occurs. The temperature of the reaction needs to be adjusted carefully, and it can generally be maintained at a moderate low temperature to prevent side reactions from breeding. Phosphorus pentachloride is an active chlorination agent. It interacts with the hydroxyl group in 4-fluorobenzenesulfonic acid, and the hydroxyl group is replaced by a chlorine atom to obtain 4-fluorobenzenesulfonyl chloride. After the reaction is completed, the product can be purified by distillation, extraction, recrystallization, etc.
Another method can start with 4-fluorobenzene. 4-fluorobenzene is first diazotized and treated with sodium nitrite and an inorganic acid (such as hydrochloric acid) at low temperature to obtain a diazonium salt. The diazonium salt is extremely active, and then reacts with sodium sulfite to introduce a sulfonic acid group to obtain a 4-fluorobenzenesulfonic acid derivative. Then the sulfonic acid derivative is treated with chlorinated reagents such as thionyl chloride. The chlorine atom of thionyl chloride interacts with the specific group of the sulfonic acid derivative, and finally 4-fluorobenzenesulfonyl chloride can be obtained. In this process, the temperature and time of the diazotization reaction, as well as the conditions of subsequent reactions, must be precisely controlled to obtain high-purity products.
When preparing 4-fluorobenzenesulfonyl chloride, all operations must strictly abide by the specifications of chemical experiments to ensure safety and ensure high quality and high yield of the product.
What to look out for when storing and transporting 4-Fluorobenzenesulfonyl Chloride
4-Fluorobenzenesulfonyl chloride is also a chemical reagent. When storing and transporting it, be sure to pay attention to many matters.
In terms of storage, the first environment. It should be placed in a cool, dry and well-ventilated place. This is because of its active nature, it is easy to react in case of moisture and heat. If it is in a humid place, water vapor will encounter it, or cause hydrolysis, which will damage its quality. And high temperature can promote its decomposition, so low temperature is appropriate. In addition, it should be stored in isolation from alkalis and alcohols. Alkalis can be neutralized with them, and alcohols can also react with them, which can damage their original properties. For storage, choose a corrosion-resistant container. Containers made of glass or certain plastic materials can also be used to prevent corrosion and leakage of the container.
As for transportation, the packaging must be tight. Make sure that the container is well sealed and there is no risk of leakage. Transportation vehicles should also be clean, dry, and away from fire and heat sources. Avoid violent vibrations and collisions on the way to prevent package damage. Transportation personnel should also be familiar with its characteristics and emergency treatment methods. If there is a leak, they can deal with it in time. All of these are for the storage and transportation of 4-fluorobenzenesulfonyl chloride to ensure its safety and quality.