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What is the main use of 2-Bromo-4- (Trifluoromethyl) Benzenesulfonyl Chloride?
2-Bromo-4- (trifluoromethyl) benzenesulfonyl chloride is an organic compound. It has a wide range of uses and is a key reagent in the field of organic synthesis.
First, it is often used to construct complex organic molecular structures containing sulfur and fluoride. With its active chemical properties of sulfonyl chloride groups, it can react with many nucleophilic reagents, such as alcohols and amines. When it encounters alcohols, a corresponding sulfonate will be formed. In organic synthesis, this sulfonate is often used as a good leaving group, which helps to advance the subsequent nucleophilic substitution reaction smoothly, thereby realizing the effective construction of carbon-carbon bonds or carbon-heteroatomic bonds. Combined with amines, sulfonamides are formed. Sulfonamides have many applications in the field of medicinal chemistry, and some have unique biological activities or can become potential drug molecules.
Second, in the field of materials science, 2-bromo-4- (trifluoromethyl) benzenesulfonyl chloride also plays an important role. Through its participation in the reaction, fluorine-containing and sulfonyl-containing structural units can be introduced into the material. The fluorine-containing structure can endow the material with unique properties, such as low surface energy and high chemical stability; the sulfonyl group can affect the solubility and hydrophilicity of the material. In this way, polymer materials with special properties can be prepared, such as high-performance coatings, special plastics, etc., to meet the needs of different fields for special properties of materials.
Third, in pharmaceutical research and development, the products of the compound involved in the synthesis may change the physicochemical properties and biological activities of molecules due to the strong electronegativity of fluorine atoms and the electronic and spatial effects of sulfonyl groups. Through rational design and synthesis, it is expected to obtain drug lead compounds with novel mechanisms of action, high activity and high selectivity, providing an important material basis for the creation of new drugs.
What are the synthesis methods of 2-Bromo-4- (Trifluoromethyl) Benzenesulfonyl Chloride
The synthesis of 2-bromo-4- (trifluoromethyl) benzenesulfonyl chloride has many paths in the past. First, benzene containing a specific substituent is used as the starting material, and the first step is bromination. During this process, it is necessary to carefully select brominating reagents, such as liquid bromine or N-bromosuccinimide (NBS), and choose suitable catalysts, such as iron powder or iron tribromide. This step is designed to introduce bromine atoms precisely at specific positions in the benzene ring.
Next, trifluoromethyl is introduced. Trifluoromethyl-containing reagents, such as Grignard reagents such as trifluoromethyl halide, are often used to connect trifluoromethyl to the benzene ring by nucleophilic substitution or similar reaction mechanisms. This step requires attention to the regulation of reaction conditions, such as temperature and solvent selection, to ensure the smooth progress and selectivity of the reaction.
After sulfonyl chlorination, the target product 2-bromo-4- (trifluoromethyl) benzenesulfonyl chloride can be obtained. The commonly used sulfonyl chlorination reagents in this step are dichlorosulfoxide (SOCl ²) or phosphorus oxychloride (POCl ²). During the reaction, it is necessary to control the reaction temperature and time, and pay attention to the anhydrous environment of the reaction system to prevent side reactions from occurring.
Another way is to introduce trifluoromethyl first, then brominate, and finally implement sulfonyl chloride. The adjustment of this sequence also needs to be carefully considered and optimized according to the difficulty, selectivity and yield of each step of the reaction. After each step of the reaction, the product is often purified by means such as column chromatography and recrystallization to obtain high-purity 2-bromo-4- (trifluoromethyl) benzenesulfonyl chloride.
What are the physical properties of 2-Bromo-4- (Trifluoromethyl) Benzenesulfonyl Chloride
2-Bromo-4- (trifluoromethyl) benzenesulfonyl chloride is an important chemical reagent in organic synthesis. Its physical properties are many and closely related to synthetic applications.
Looking at its properties, this is a solid or liquid, depending on the specific purity and environmental conditions. Generally speaking, pure products or colorless to light yellow liquids, if they contain impurities, the color may change. It has a pungent smell, because the sulfonyl chloride group is active, volatile and irritating, it must be used with caution to prevent irritation to the respiratory tract and skin.
The melting point and boiling point are discussed. The melting point is between -10 ° C and 10 ° C, and the boiling point is in the range of 270 ° C - 290 ° C. This melting boiling point characteristic is derived from the intermolecular forces, including Van der Waals forces and polar effects. The bromine atom, trifluoromethyl methyl group and sulfonyl chloride group in the molecule affect the intermolecular distance and the strength of the force, resulting in the melting boiling point in a specific range. This property is crucial for separation and purification, and can be separated according to the difference in melting boiling point by means of distillation and recrystallization.
Its density is greater than that of water, about 1.9 - 2.1 g/cm ³. This is because the relative atomic weight of bromine and fluorine atoms in the molecule is large, which increases the weight per unit volume. The density characteristic is of great significance in reactions or operations involving liquid-liquid separation. If it is reacted in an aqueous phase system, it will be in the lower layer due to its high density, which is conducive to separation and subsequent processing.
In terms of solubility, it can be soluble in common organic solvents, such as dichloromethane, chloroform, toluene, etc. Because these organic solvents and 2-bromo-4- (trifluoromethyl) benzenesulfonyl chloride molecules can form similar intermolecular forces, following the principle of "similar miscibility". In organic synthesis, this solubility can provide a reaction medium that allows the reactants to fully contact and promote the reaction. However, it has poor solubility in water and is prone to hydrolysis in water to generate corresponding sulfonic acid and hydrogen chloride gas. This hydrolysis property is also an important manifestation of its physical and chemical properties, and it is necessary to pay attention to waterproofing during storage and use.
The physical properties of 2-bromo-4- (trifluoromethyl) benzenesulfonyl chloride have a profound impact on its application in the field of organic synthesis. Familiarity with and good use of these properties can better control the relevant chemical reactions and achieve the desired synthesis goals.
What are the chemical properties of 2-Bromo-4- (Trifluoromethyl) Benzenesulfonyl Chloride
2-Bromo-4- (trifluoromethyl) benzenesulfonyl chloride, which is an important chemical substance in the field of organic synthesis. It has unique chemical properties and has a significant impact on organic synthesis reactions.
Looking at its chemical activity, the activity of the sulfonyl chloride group (-SO 2O Cl) is very high. This group easily reacts with nucleophiles. If it encounters alcohols, it can be formed by nucleophilic substitution reaction. In this reaction, the oxygen atom of the alcohol attacks the sulfur atom of the sulfonyl chloride with its lone-pair electrons, and the chlorine atom leaves as a leaving group, thus forming a sulfonate product. This reaction condition is usually mild, and it is often used in organic synthesis to construct compounds containing sulfur ester structures. It is widely used in the fields of medicinal chemistry and materials science.
Furthermore, the halogen atom bromine is also of great significance in molecules. Bromine atoms can participate in many reactions, such as metal-catalyzed coupling reactions. In palladium-catalyzed cross-coupling reactions, bromine atoms can react with organoboronic acids or organotin reagents to achieve the construction of carbon-carbon bonds. This reaction greatly expands the application range of this compound in the synthesis of complex organic molecules, assisting in the synthesis of organic materials and biologically active molecules with specific structures and functions.
The presence of trifluoromethyl (-CF 🥰) significantly affects the physical and chemical properties of molecules. Trifluoromethyl has strong electron absorption, which can reduce the electron cloud density of the benzene ring, which in turn affects the reactivity of other substituents on the benzene ring. Due to its strong electron absorption effect, it can enhance the stability and fat solubility of molecules. In drug development, the introduction of trifluoromethyl can often improve the metabolic stability and bioavailability of drugs, and enhance the efficacy of drugs.
In addition, 2-bromo-4 - (trifluoromethyl) benzenesulfonyl chloride is sensitive to water and air. When exposed to water, the sulfonyl chloride group is easily hydrolyzed to form corresponding sulfonic acid and hydrogen chloride. This hydrolysis reaction is an irreversible process. When storing and using the compound, it is necessary to ensure a dry environment and avoid contact with water vapor to prevent deterioration and affect its application effect in organic synthesis reactions.
2-Bromo-4- (Trifluoromethyl) Benzenesulfonyl Chloride in Storage and Transportation
2-Bromo-4- (trifluoromethyl) benzenesulfonyl chloride is a chemical substance. During storage and transportation, many matters must be observed.
This substance is corrosive and can cause skin, eyes, and respiratory injuries when touched. Therefore, when storing, it should be placed in a cool, dry and well-ventilated place. Keep away from fires and heat sources, and must not be mixed with flammable, flammable substances, and alkalis and alcohols. Because of its exposure to water or moisture, it is easy to react and release toxic and corrosive fumes.
Tight packaging is essential. Suitable packaging materials must be used to prevent leakage. When handling, be sure to handle it with care to avoid damage to its container. If you are engaged in related operations, the operator should wear protective clothing, protective gloves and goggles in front of them to prevent accidents.
When transporting, follow relevant regulations and standards. Select qualified transportation enterprises and vehicles to ensure safety during transportation. Transportation vehicles should be equipped with emergency treatment equipment. If there is a leak, they can be disposed of quickly.
In short, the storage and transportation of 2-bromo-4- (trifluoromethyl) benzenesulfonyl chloride must be treated with caution in terms of safety and protection, so as to avoid disasters and ensure the safety of people and things.