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What is the chemical structure of N- (2,4,6-triisopropylbenzenesulfonyl) imidazole?
(2,4,6-triisopropylbenzenesulfonyl chloride) is a commonly used reagent in organic synthesis. Its chemical structure is quite unique, consisting of a benzene ring, a sulfonyl chloride group and three isopropyl groups. The
benzene ring, as the core skeleton of the compound, endows the whole molecule with aromaticity and stability. The benzene ring is composed of six carbon atoms connected to each other in the form of conjugated double bonds to form a stable planar ring structure.
sulfonyl chloride (-SO 2O Cl) is the key active group of this compound. In this group, the sulfur atom is connected to two oxygen atoms by double bonds, and is also connected to the chlorine atom. The valence of the sulfur atom is + 6. Due to the fact that both oxygen and chlorine are highly electronegative elements, the electron cloud density around the sulfur atom decreases, resulting in higher reactivity of the sulfonyl chloride group. In many organic reactions, sulfonyl chloride groups are very easy to react with nucleophilic reagents, and chlorine atoms can be replaced by nucleophilic groups to form new chemical bonds. It is often used to introduce sulfonyl groups to prepare sulfonamides, sulfonates and many other organic compounds.
Three isopropyl groups (-CH (CH 🥰) -2) are attached to the benzene ring. Isopropyl belongs to alkyl group, which has the electron cloud density of benzene ring, which can increase the electron cloud density of benzene ring, affect the electron cloud distribution of benzene ring, and then change the reactivity and selectivity of benzene ring. Moreover, the steric resistance of isopropyl group is large, which will affect the stereochemical process of the compound participating in the reaction. In some reactions, it can guide the reaction in a specific direction, and affect the structure and configuration of the reaction product.
In summary, the chemical structure of (2,4,6-triisopropylbenzenesulfonyl chloride) endows the compound with unique physical and chemical properties due to the interaction of benzene ring, sulfonyl chloride group and isopropyl group, which makes it show important application value in the field of organic synthetic chemistry.
What are the main uses of N- (2,4,6-triisopropylbenzenesulfonyl) imidazole?
N- (2,4,6-triisopropylbenzenesulfonyl) azide is an important reagent in organic synthesis, and its main uses are as follows:
First, it is used to construct nitrogen-containing heterocycles. In the field of organic synthesis, nitrogen-containing heterocyclic compounds widely exist in the structures of many drugs and natural products. This azide reagent can form various nitrogen-containing heterocycles through cyclization reaction, such as triazole, tetrazole, etc. For example, under specific catalytic conditions, N- (2,4,6-triisopropylbenzenesulfonyl) azide undergoes [3 + 2] cycloaddition reaction with alkynes to efficiently generate 1,2,3-triazole compounds. Such reaction conditions are relatively mild and the products have good regioselectivity, which is widely used in the fields of medicinal chemistry and materials science.
Second, participate in the azene transfer reaction. This reagent can release azene intermediates, which are highly active and can react with a variety of substrates, such as insertion of carbon-hydrogen bonds, carbon-carbon double bond addition, etc. For example, under appropriate initiation conditions, azene can be inserted into the carbon-hydrogen bond of alkanes to form new carbon-nitrogen bonds, introducing nitrogen-containing functional groups to organic molecules, which greatly enriches organic synthesis strategies and is of great significance for the construction of complex organic molecular structures.
Third, as an alternative reagent for diazonium compounds. In some reactions, diazonium compounds have many limitations in use due to their high activity and high risk. N- (2,4,6-triisopropylbenzenesulfonyl) azide can be used as a substitute for diazo compounds in some scenarios to achieve similar reaction conversion while avoiding the risk of diazo compounds. For example, in some metal-catalyzed carbene transfer reactions, the azide reagent can be decomposed to produce carbene-like active intermediates to complete the substrate functionalization reaction, providing a safer choice for organic synthesis.
What is the synthesis method of N- (2,4,6-triisopropylbenzenesulfonyl) imidazole?
To prepare N- (2,4,6-triisopropylbenzenesulfonyl) azide, the synthesis method is as follows:
First take 2,4,6-triisopropylbenzenesulfonic acid as the starting material, place it in the reaction kettle with thionyl chloride, and apply moderate heat to make it fully react. The main point of this reaction is to convert the sulfonic acid group into a sulfonyl chloride group. The chemical reaction formula is as follows:
(2,4,6-triisopropylbenzenesulfonic acid) + SOCl ² → (2,4,6-triisopropylbenzenesulfonic acid chloride) + HCl ↑ + SO ³ ↑
After the reaction is completed, the unreacted sulfoxide and by-products are removed by distillation to obtain a pure 2,4,6-triisopropylbenzenesulfonic acid chloride.
The resulting 2,4,6-triisopropylbenzenesulfonic acid is taken at times, dissolved in a suitable organic solvent, such as dichloromethane, and cooled to a suitable low temperature, such as about 0 ° C. The aqueous solution of sodium azide is slowly added dropwise. When adding dropwise, it must be stirred continuously to ensure a uniform reaction. The essence of this step is the substitution reaction of sulfonyl chloride group with azide ion to form the target product N- (2,4,6 -triisopropylbenzenesulfonyl) azide. The chemical reaction formula is as follows:
(2,4,6-triisopropylbenzenesulfonyl chloride) + NaN 🥰 → N- (2,4,6-triisopropylbenzenesulfonyl) azide + NaCl
After the reaction is completed, the organic phase is separated from the liquid and washed with water, sodium bicarbonate solution and saturated salt water to remove unreacted sodium azide and other impurities. The organic phase is then dried with anhydrous sodium sulfate to remove the residual moisture. Finally, the organic solvent is evaporated by reduced pressure distillation to collect the appropriate boiling point fraction to obtain pure N- (2,4,6-triisopropylbenzenesulfonyl) azide. During the entire synthesis process, attention should be paid to the reaction temperature, material ratio, and fine operation to ensure the smooth progress of the reaction and improve the purity and yield of the product.
What are the precautions for N- (2,4,6-triisopropylbenzenesulfonyl) imidazole in the reaction?
In the reaction of N- (2,4,6-triisobutylphenoxyethanol) amide, there are many precautions that need to be paid attention to.
First, the ratio of the reactants must be precisely controlled. The ratio of this compound to other reactants has a profound impact on the reaction process and product purity. Improper proportions may cause incomplete reactions, or generate many by-products, which greatly increases the difficulty of product separation and purification.
Second, the reaction temperature needs to be carefully regulated. If the temperature is too high, the reaction rate will accelerate, but it may cause side reactions and cause product structure changes; if the temperature is too low, the reaction rate will be slow, take too long, and may not achieve the desired reaction effect. When looking for a suitable temperature range based on the reaction mechanism and past experience, and with the help of temperature control equipment to ensure temperature stability.
Third, the reaction time cannot be ignored. If the reaction time is too short, the reaction may not be fully carried out, and the yield is low; if the reaction time is too long, it will not only waste time and energy, but also cause negative conditions such as product decomposition. Experimental monitoring methods, such as chromatographic analysis, should be used to grasp the reaction process in a timely manner to determine the best reaction time.
Fourth, the choice of solvent is crucial. Different solvents have different effects on the solubility and reactivity of reactants. It is necessary to select a solvent that has good solubility to the reactants, can promote the reaction, and does not have adverse reactions with the reactants and products to create a suitable reaction environment.
Fifth, the pH of the reaction system will also affect the reaction. Some reactions can proceed smoothly under specific pH conditions, and it is necessary to maintain the pH stability of the system with the help of buffer solutions and other means to ensure that the reaction occurs according to the expected path.
Finally, safety protection must not be slack. This compound and the reagents used in the reaction process may have toxic, corrosive and other dangerous properties. Experimenters should wear suitable protective equipment, such as gloves, goggles, etc., and the experimental operation should be carried out in a well-ventilated environment to prevent the accumulation of harmful gases and endanger personal safety.
What is the market price of N- (2,4,6-triisopropylbenzenesulfonyl) imidazole?
Today, the market price of 2,4,6-triisopropylbenzaldehyde is related to many factors, which is difficult to hide in one word.
First, the price of raw materials has a great impact. The preparation of 2,4,6-triisopropylbenzaldehyde requires specific raw materials. If the price of raw materials fluctuates, the price of the product will also fluctuate. If the source of raw materials is scarce, or the supply changes due to season, origin, etc., the price will be affected.
Second, the simplicity of the process is also the key. The production of this substance requires high technology and special equipment. If the process is difficult, the investment of manpower, material resources and financial resources is large, and the cost increases, the market price will rise. On the contrary, if the process is simple and the cost is reduced, the price will also be reduced.
Third, market supply and demand determine the price. If the market demand for this product is strong, but the supply is limited, the supply is in short supply, and the price will rise. On the contrary, if the market demand is low and the supply is excessive, merchants may reduce the price for promotional sales.
Fourth, the competitive situation should not be ignored. There are many companies in the industry that produce this product, and the competition is fierce. In order to compete for market share, some companies may use price as a means or reduce the price to attract customers, or because of differences in quality and service.
Fifth, external factors such as policies, regulations, and taxes can also affect the price. Environmental protection policies are becoming stricter. In order for enterprises to meet standards or increase environmental protection investment, costs will rise and prices will rise. Changes in tax policies will also affect enterprise costs and pricing.
In summary, the market price of 2,4,6-triisopropylbenzaldehyde is in dynamic change due to the interaction of raw materials, processes, supply and demand, competition, policies and many other factors. To know the exact price, it is necessary to pay attention to the market conditions in real time and consider all factors comprehensively.