Chemical Formula | C5H4FNO2S |
Molecular Weight | 161.15 |
Appearance | Solid (usually white to off - white) |
Physical State At Room Temp | Solid |
Melting Point | 105 - 107 °C |
Solubility In Water | Low solubility |
Solubility In Organic Solvents | Soluble in many organic solvents like dichloromethane, chloroform |
Pka | No widely - known value |
Vapor Pressure | Very low at room temperature |
What is the main use of pyridine-2-sulfonyl fluoride?
Pyridine-2-sulfonyl fluoride has a wide range of uses. In the field of organic synthesis, it is a crucial reagent. Because of its unique reactivity of sulfonyl fluoride groups in its structure, it can participate in many key chemical reactions.
One of them can be used to construct carbon-sulfur bonds. In organic synthesis, the formation of carbon-sulfur bonds is often used as a specific reagent, and pyridine-2-sulfonyl fluoride plays an important role in this. By reacting with carbon-containing nucleophiles, carbon-sulfur bonds can be efficiently formed, and then organic sulfides with diverse structures can be constructed. Such compounds have important applications in medicine, materials and other fields.
Second, it has made significant contributions to the field of medicinal chemistry. It can be used as a key fragment in the modification of lead compounds. In drug development, it is often necessary to optimize the structure of existing lead compounds to improve drug efficacy and reduce toxicity. Pyridine-2-sulfonyl fluoride can be introduced into lead compound molecules to optimize the interaction between compounds and targets by changing the molecular electron cloud distribution and spatial configuration, etc., and help to discover better drug molecules.
Furthermore, it has also been involved in the field of materials science. It can participate in the synthesis and modification of polymer materials. By copolymerizing with polymer monomers or modifying the surface of polymers, novel properties of materials are endowed, such as improving the hydrophilicity of materials and improving the chemical stability of materials, to expand the application scenarios of materials.
In conclusion, pyridine-2-sulfonyl fluoride plays an important role in many fields such as organic synthesis, medicinal chemistry, and materials science due to its unique chemical properties, promoting the continuous development and progress of various fields.
What are the chemical properties of pyridine-2-sulfonyl fluoride
Pyridine-2-sulfonyl fluoride is one of the organic compounds. Its chemical properties are particularly interesting and have multiple characteristics.
In this compound, the presence of fluorine atoms gives it unique activity. Fluorine atoms have high electronegativity, which increases the reactivity of pyridine-2-sulfonyl fluoride. It can participate in nucleophilic substitution reactions. Under suitable conditions, fluorine atoms can be replaced by nucleophilic reagents. After the fluorine atoms leave, the remaining pyridine-2-sulfonyl groups can exist stably.
Pyridine ring also has a significant impact on its chemical properties. The pyridine ring is aromatic, and the electron cloud distribution is special, which can undergo electrophilic substitution reaction, but the reaction activity is slightly lower than that of the benzene ring. The electron cloud density on the ring is reduced due to the electron-withdrawing effect of the nitrogen atom of the pyridine ring.
The sulfonyl group of pyridine-2-sulfonyl fluoride is also an important active site. Sulfonyl groups have high oxidation states and can participate in various redox reactions. And sulfonyl groups can form hydrogen bonds or other non-covalent interactions with various organic molecules, which has potential applications in molecular recognition and supramolecular chemistry.
Furthermore, its stability is also an important property. Under normal conditions, pyridine-2-sulfonyl fluoride can exist stably, but when it encounters specific reagents or conditions, such as a strong basic environment, or reactions such as hydrolysis, its structure changes.
In short, pyridine-2-sulfonyl fluoride exhibits unique and rich chemical properties due to the synergistic action of fluorine atoms, pyridine rings and sulfonyl groups, and has important research and application value in many fields such as organic synthesis and medicinal chemistry.
What are the precautions for pyridine-2-sulfonyl fluoride during use?
Pyridine-2-sulfonyl fluoride (pyridine-2-sulfonyl fluoride) is a very important chemical reagent, and many things must be paid attention to during use.
Bear the brunt, and safety protection must not be ignored. This reagent is toxic and irritating, and can cause physical discomfort if it touches the skin, eyes or inhales its vapors. Therefore, be sure to wear appropriate protective equipment, such as laboratory clothes, gloves and protective glasses, when operating, to ensure your own safety. And the operation should be carried out in a well-ventilated fume hood to prevent the accumulation of harmful gases.
Furthermore, care must be taken when storing. Pyridine-2-sulfonyl fluoride should be stored in a cool, dry and ventilated place, away from sources of ignition and oxidants. Due to its active chemical properties, improper storage is prone to deterioration or dangerous reactions. It is necessary to strictly follow the relevant storage specifications, and regularly check the storage conditions and reagent status.
When using, accurate dosage control is indispensable. This reagent has high reactivity, and the dosage has a great impact on the reaction result. It must be accurately measured according to the specific reaction needs, with the help of accurate measuring tools. Do not increase or decrease the dosage at will, so as not to cause adverse effects on the reaction process and product purity.
In addition, its chemical properties should also be well known. Pyridine-2-sulfonyl fluoride will react with a variety of substances, and it is necessary to clarify its compatibility with other reagents involved in the reaction before use. If you mix incompatible substances rashly, it is very likely to cause violent reactions, which may even endanger safety.
Finally, after the experiment is completed, it is essential to properly dispose of the remaining reagents and waste. It must not be discarded at will, and it must be treated harmlessly in accordance with relevant environmental regulations to prevent pollution to the environment.
What is the synthesis method of pyridine-2-sulfonyl fluoride
The synthesis of pyridine-2-sulfonyl fluoride (pyridine-2-sulfonyl fluoride) is a delicate problem in organic synthetic chemistry. To make this compound, there are many paths to follow. Let's describe one of the commonly used methods.
The first starting material is pyridine, which plays a key role in the reaction because of its unique electronic properties. Pyridine reacts with sulfonyl chloride reagents, such as chlorosulfonic acid or sulfur trioxide-pyridine complexes, under suitable conditions. This step requires careful regulation of temperature, reactant ratio and reaction time. Usually in a low temperature environment, such as between 0 ° C and 5 ° C, the sulfonyl chloride reagent is slowly dropped into the pyridine to prevent the reaction from being overreacted and unnecessary by-products are formed.
After the first step of the reaction is completed, the pyridine-2-sulfonic acid intermediate is formed. This intermediate needs to be further converted to sulfonyl fluoride. It is often reacted with fluorinated reagents, such as potassium fluoride, silver fluoride, etc. This step of the reaction is mostly carried out in polar aprotic solvents, such as dimethyl sulfoxide (DMSO) or N, N-dimethylformamide (DMF). Such solvents can effectively dissolve the reactants and fluorinated reagents and promote the reaction. The reaction temperature also needs to be precisely controlled, usually between 60 ° C and 80 ° C, with continuous stirring for several hours to make the reaction sufficient.
After the reaction is completed, the product needs to be separated and purified. The target product is separated from the reaction mixture by column chromatography with a suitable silica gel as the stationary phase and a suitable eluent selected. After fine operations such as recrystallization, high-purity pyridine-2-sulfonyl fluoride can be obtained.
Although this synthesis method is complicated, each step is closely connected, and a slight difference in the pool will affect the purity and yield of the product. It is necessary for the synthesizer to operate carefully and precisely control the reaction conditions in order to obtain satisfactory results.
What are the reactions of pyridine-2-sulfonyl fluoride with other compounds?
Pyridine-2-sulfonyl fluoride (pyridine-2-sulfonyl fluoride) is a key reagent in organic synthesis. It can react with a variety of compounds to form other organic compounds. The following is a brief description of its common reactions:
1. ** Nucleophilic Substitution Reaction **: The fluorine atoms in this reagent are highly active and can be easily replaced by nucleophilic reagents. For example, when they meet alcohols, the fluorine atoms can be replaced by alkoxy groups to form pyridine-2-sulfonate esters. The beauty of this reaction is that different alcohols can be selected to prepare sulfonates with diverse structures, which are widely used in organic synthesis. For example, taking ethanol as an example, the reaction equation is roughly as follows: pyridine-2-sulfonyl fluoride + ethanol → pyridine-2-sulfonate ethyl ester + hydrogen fluoride. During the reaction, a base is usually required as a catalyst to push the reaction to the right.
2. ** Reacts with amines **: The nitrogen atom of the amine compound is rich in electrons and has nucleophilic properties. It can attack the sulfur atom of pyridine-2-sulfonyl fluoride, causing the fluoride ion to leave to form pyridine-2-sulfonamide compounds. This kind of reaction is of great significance in the field of drug synthesis, because the sulfonamide structure is commonly found in many drug molecules, which can endow drugs with specific biological activities. For example, the reaction of aniline with pyridine-2-sulfonyl fluoride can generate the corresponding pyridine-2-sulfonylaniline.
3. ** Reacts with active hydrogen-containing compounds **: Compounds containing active hydrogen such as phenols and thiols can also react with pyridine-2-sulfonyl fluoride. Take phenol as an example, the hydrogen of phenolic hydroxyl is replaced by pyridine-2-sulfonyl to form pyridine-2-sulfonate phenolic esters. This reaction may have applications in the field of materials science, such as the preparation of some functional polymer materials, which can be imparted unique properties by introducing pyridine-2-sulfonyl groups.