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What is the main use of 2- (Trifluoromethoxy) Benzene-1-Sulfonyl Chloride?
2-%28Trifluoromethoxy%29Benzene-1-Sulfonyl Chloride, Chinese name 2 - (trifluoromethoxy) benzenesulfonyl chloride, is a crucial chemical reagent in the field of organic synthesis and has a wide range of uses in many fields.
One of them is in the field of medicinal chemistry. In the process of drug development, many drug molecules need to introduce specific functional groups to optimize their pharmacological activity, pharmacokinetic properties and bioavailability. 2 - (trifluoromethoxy) benzenesulfonyl chloride has trifluoromethoxy and sulfonyl chloride functional groups, which can participate in a variety of chemical reactions. Through nucleophilic substitution, sulfonyl chloride can react with nucleophilic reagents containing nitrogen, oxygen, sulfur, etc., to form sulfonamides, sulfonates and other structures. In the synthesis of some antibacterial and antiviral drugs, the introduction of such structures can enhance the interaction between the drug and the target, and improve the efficacy of the drug. For example, in the development of a new antiviral drug, this compound is used to react with a specific nitrogen-containing heterocycle to successfully construct key pharmacophore, which significantly enhances the inhibitory activity of the drug against viral proteases.
Second, in the field of materials science, it also plays an important role. In the preparation of high-performance polymer materials, 2 - (trifluoromethoxy) benzenesulfonyl chloride can participate in the polymerization reaction as a functional monomer. The strong electron absorption and unique electronic effect of trifluoromethoxy can endow polymer materials with special properties. For example, its introduction into the synthesis of polyester materials can improve the chemical resistance, thermal stability and surface properties of the materials. The prepared polyester material is used as a high-performance coating material in the aerospace field, which can effectively resist severe environmental erosion and ensure the safe and stable operation of aircraft components.
Third, in the field of organic synthetic chemistry, it can be used as an important intermediate to construct complex organic molecular structures. By rationally designing the reaction route and taking advantage of the activity of sulfonyl chloride groups, a multi-step reaction can be carried out to construct carbon-carbon and carbon-heteroatomic bonds. For example, when synthesizing bioactive natural product analogs, this compound is used as the starting material to successfully construct a complex thick ring structure through multi-step reaction, providing an effective way for the total synthesis and structural modification of natural products.
What are the physical properties of 2- (Trifluoromethoxy) Benzene-1-Sulfonyl Chloride
2 - (trifluoromethoxy) benzene-1 -sulfonyl chloride, this material property is special, related to chemical things. Its shape is colorless to light yellow liquid, stable at room temperature and pressure, but easy to change when exposed to water or humid air.
Looking at its melting point, it is difficult to determine exactly, because it is liquid at room temperature, so it is fresh to say that the melting point is the main physical property. The boiling point is about a specific temperature range, but it varies depending on specific conditions. Usually under appropriate heating, it can be seen that it boils into a gaseous state.
In terms of solubility, it can be well miscible in organic solvents such as dichloromethane and chloroform. This property makes it possible to find a suitable solvent environment when building a reaction system for organic synthesis. In water, due to its chemical structure containing fluorine and sulfonyl chloride groups, it reacts rapidly in contact with water and hydrolyzes to generate corresponding sulfonic acid and hydrogen chloride gas. This hydrolysis reaction is violent, making it difficult to dissolve in water.
Its density is larger than that of water. During operations such as liquid separation, if the aqueous phase is involved, this property can make the stratification clear and facilitate subsequent separation processes. And this object has a pungent smell. During operation, careful protection is required, as it may irritate the respiratory tract, eyes and skin, causing discomfort and even damage. When storing, keep in a dry, cool and well-ventilated place to avoid contact with water and alkaline substances to prevent unexpected chemical reactions.
What are the chemical properties of 2- (Trifluoromethoxy) Benzene-1-Sulfonyl Chloride
2-%28Trifluoromethoxy%29Benzene-1-Sulfonyl+Chloride is 2- (trifluoromethoxy) benzene-1-sulfonyl chloride, which has different physical properties and is of great value for investigation.
In terms of shape and color, it is often colorless to light yellow liquid. It is clear and shiny, and it may be slightly shiny in the sun. If you smell it, it has a pungent smell. This smell is very strong, which can cause nasal and throat discomfort, warning that it is irritating.
When it comes to chemical activity, the sulfonyl chloride group (-SO 2O Cl) in 2- (trifluoromethoxy) benzene-1-sulfonyl chloride is very active. In contact with water, it is easy to react with hydrolysis, and the corresponding sulfonic acid and hydrogen chloride gas are rapidly produced. The hydrolysis process is rapid, which can cause the temperature of the system to change abruptly, and the hydrogen chloride to escape, which is like a white fog.
In the field of organic synthesis, this is the key intermediate. It can combine with alcohols and give rise to sulfonate substances through substitution reaction. This reaction is controllable, and when conditions are suitable, the yield is quite good. Sulfonates are useful in medicine, materials and other fields. When they meet amines, they also react to form sulfonamides. Such products are common structural units in drug development and have diverse biological activities.
2- (trifluoromethoxy) benzene-1 -sulfonyl chloride has unique properties due to its trifluoromethoxy (-OCF). Trifluoromethoxy has strong electron-absorbing properties, which can change the electron cloud distribution of compounds, thereby affecting their reactivity and physical properties. Therefore, compounds containing this structure often have good lipophilic properties, which can help drugs penetrate biofilms and improve bioavailability in drug molecular design.
However, it should be noted that 2- (trifluoromethoxy) benzene-1 -sulfonyl chloride is corrosive and has serious damage to the skin, eyes and respiratory tract. When operating, it is necessary to strictly follow safety procedures, wear protective equipment, and place it in a well-ventilated place to avoid hazards.
What are the synthesis methods of 2- (Trifluoromethoxy) Benzene-1-Sulfonyl Chloride
2-%28Trifluoromethoxy%29Benzene-1-Sulfonyl Chloride, that is, 2 - (trifluoromethoxy) benzene-1 - sulfonyl chloride, is synthesized as follows:
First, 2-hydroxybenzene sulfonyl chloride is used as the starting material. In the reactor, 2-hydroxybenzene sulfonyl chloride is placed, dissolved in an appropriate amount of organic solvent such as N, N - dimethylformamide (DMF), so that it is uniformly dispersed. In this solution, slowly add a trifluoromethylating agent, such as sodium trifluoromethylsulfonate (CF < SO < Na). This process needs to be carefully controlled, usually maintained at a low temperature, between about 0 ° C and 5 ° C, to prevent the growth of side reactions. Add an acid binding agent, such as potassium carbonate (K ² CO 🥰), to neutralize the acid produced by the reaction, and promote the reaction to proceed in a positive direction. After the raw materials are added, heat up to room temperature, and continue to stir the reaction number. The reaction progress was monitored by thin-layer chromatography (TLC) until the raw material point was basically eliminated and the reaction was complete. After that, the reaction solution was diluted with water, and then extracted with an organic solvent such as dichloromethane to collect the organic phase. The organic phase was washed with saturated saline water and dried with anhydrous sodium sulfate. After filtering to remove the desiccant, the organic solvent was distilled under reduced pressure to obtain a crude product. The crude product was separated and purified by column chromatography. The mixed solvent of petroleum ether and ethyl acetate was used as the eluent to obtain pure 2- (trifluoromethoxy) benzene-1-sulfonyl chloride.
2- (trifluoromethoxy) benzoic acid can also be used as the starting material. Put 2- (trifluoromethoxy) benzoic acid into the reaction vessel, add an appropriate amount of sulfoxide chloride (SOCl ²), and add a few drops of N, N-dimethylformamide as the catalyst. Heat reflux reaction, sulfoxide chloride reacts with carboxyl group to form acid chloride. After the reaction is completed, the excess sulfoxide chloride is removed by reduced pressure distillation to obtain the crude product. The crude product is purified by means of reduced pressure distillation or recrystallization to obtain the target product 2 - (trifluoromethoxy) benzene-1 - sulfonyl chloride.
Furthermore, 2 - chlorobenzene sulfonyl chloride is used as the starting material and reacts with sodium trifluoromethoxide (CF
ONa). In a suitable solvent such as tetrahydrofuran (THF), 2 - chlorobenzene sulfonyl chloride is mixed with sodium trifluoromethoxide and heated. During the reaction, the chlorine atom is replaced by trifluoromethoxy to form 2 - (trifluoromethoxy) benzene-1 - sulfonyl chloride. After the reaction is completed, the treatment method is the same as before, and the pure product is obtained through separation and purification steps.
What should be paid attention to when storing and transporting 2- (Trifluoromethoxy) Benzene-1-Sulfonyl Chloride?
2 - (trifluoromethoxy) benzene-1 -sulfonyl chloride, this material is strong and sensitive, and many matters need to be paid attention to during storage and transportation.
First of all, store, must find a cool, dry and well-ventilated place. Because it is easy to decompose when heated, if it is in a high temperature environment, it may change unexpectedly. The temperature should be controlled within a specific range and should not exceed the specified limit. In addition, this agent is highly corrosive, and the storage container must be corrosion-resistant, such as glass, specific plastic or stainless steel materials, to prevent material leakage caused by corrosion of the container. And it needs to be tightly sealed to avoid contact with air and moisture, because it is easy to react violently when exposed to water, generating strong acids and other substances, which not only damages materials, but also increases safety hazards.
As for transportation, there are also many details. When handling, the operation must be light, and must not be dropped or pressed to avoid package damage. Transportation vehicles should be selected with good protection and ventilation facilities, and must be kept away from fire and heat sources. At the same time, transportation personnel should be familiar with the characteristics of this object and emergency treatment methods. If there is a leak on the way, they can quickly and properly dispose of it. Packaging also needs to be compliant, and clear warning signs should be posted so that relevant personnel can see it at a glance and treat it with caution. In this way, the safety of storage and transportation can be guaranteed to avoid accidental disasters.