3 4 fluorobenzenethiol applications properties synthesis
Method of Synthesis of 3,4-Fluorothiophenol
To prepare 3,4-fluorothiophenol
, there are many ways. First, start with fluorine-containing benzene halide and react with sulfur-containing reagents. If 3,4-difluorobromobenzene is used as a substrate, in an appropriate solvent, with the help of a catalyst, it interacts with sodium hydrosulfide. During the reaction, it is necessary to control the temperature moderately to promote the reaction to produce 3,4-fluorothiophenol. And the nature of the solvent and the amount of catalyst have a significant impact on the rate and yield of the reaction. Second, fluorine-containing phenolic compounds can also be used as raw materials and obtained by thiogeneration. This process requires the selection of appropriate thiophenol reagents, such as Lawson's reagent, under specific reaction conditions, to achieve the conversion of phenolic hydroxyl groups to thiophenol groups.
The characteristic of properties
3,4 -fluorobenzothiophenol has special properties. At room temperature, it is mostly liquid and colorless to light yellow. It has a pungent smell, which is the common property of thiophenol compounds. Its physical properties such as boiling point and melting point are determined by the interaction of fluorine atoms and thiophenol groups in the molecule. In terms of chemical properties, its thiophenol groups have high reactivity. Because there are lone pairs of electrons on sulfur atoms, electrons are easily given, thus participating in nucleophilic substitution reactions. And the fluorine atom on the phenyl ring can reduce the electron cloud density of the phenyl ring due to its high electronegativity, and the reactivity of the thiophenol group can also be adjusted. For example, in the nucleophilic substitution reaction with halogenated hydrocarbons, the sulfur atom of the thiophenol group can attack the α-carbon of the halogenated hydrocarbons, and the halogen atom leaves to form thioether compounds.
Application field
3,4-fluorothiophenol is important in many fields. In the field of organic synthesis, it is a key intermediary. It can be used to construct complex organic molecules containing sulfur and fluorine. For example, in medicinal chemistry, fluorothioether drugs with unique physiological activities can be prepared through the reactions they participate in. Due to the introduction of fluorine atoms, the pharmacokinetic properties of compounds such as lipid solubility and metabolic stability can be changed, and the thioether structure can interact specifically with biological targets. In the field of materials science, 3,4-fluorothiophenol can be used to prepare functional materials. For example, in the preparation of self-assembled monolayers, it can form an ordered molecular film on the metal surface through the strong interaction of sulfur atoms with the metal surface, thereby imparting special physical and chemical properties to the metal surface, such as corrosion resistance, hydrophilic and hydrophobic regulation properties.
