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What is the chemical structure of bis (tert-butyl) phenyliodonium chloride?
Bis (tert-butyl) silyl ether oxide halide, a class of silicone compounds, is very important in the field of organic synthesis. In its chemical structure, the silicon atom is connected to two tert-butyl groups and one oxygen atom, and the oxygen atom is combined with the halogen atom.
Looking at its structure, the silicon atom is the central atom, and its outer electronic configuration allows it to form covalent bonds with multiple atoms. Two tert-butyl groups, which are large substituents, have a significant impact on the chemical environment around the silicon atom by virtue of their steric hindrance effect. This steric hindrance not only enhances the stability of the compound, but also guides the selectivity of the reaction in the chemical reaction.
The oxygen atom is connected to the silicon atom. Because the electronegativity of oxygen is higher than that of silicon, the silicon-oxygen bond presents a certain polarity. This polarity not only affects the physical properties of the molecule, such as boiling point and solubility, but also has great significance for its chemical reactivity. The lone pair of electrons on the oxygen atom makes it possible to participate in various coordination and chemical reactions as an electron donor.
The halogen atom is connected to the oxygen atom, and the electronegativity of the halogen atom is very high, which further strengthens the polarity of the molecule. Different halogen atoms give compounds different reactivity due to differences in atomic radius and electron cloud distribution. For example, fluorine atoms have small atomic radius and high electronegativity, and the compounds connected to them usually have unique chemical properties; while chlorine, bromine, and iodine atoms have different reactivity due to their large atomic radii.
The structural characteristics of such compounds make them can be used as protective groups to protect hydroxyl and other functional groups in organic synthesis; they can also participate in many reactions such as nucleophilic substitution and elimination, providing an effective way to construct complex organic molecular structures. Its unique chemical structure and properties make bis (tert-butyl) silyl ether oxide halide an object of much attention in organic synthesis chemistry.
What are the main uses of bis (tert-butyl) phenyl iodonium chloride?
Bis (tert-butyl) silyl ether halides are widely used in the industrial industry. There are three main ways, with Chen Ruzuo.
One is used as a protective group. In the art of organic synthesis, it is often necessary to protect specific functional groups from being disturbed during reactions. Bis (t-butyl) silyl ether halides can form ethers with alcohols to protect hydroxyl groups. After the rest of the reaction is completed, the protective group is removed, and the properties of the complex hydroxyl group. For example, if you synthesize a complex steroid compound with many hydroxyl groups, use bis (t-butyl) silyl ether halide to protect one hydroxyl group, so that other groups are reacted, and then de-protected to obtain a pure product. This has high selectivity for retaining hydroxyl groups, and the conditions are mild, which does not damage other sensitive groups.
Second, it is a raw material for the reaction of organometallic reagents. It can react with metal reagents, such as Grignard reagent or lithium reagent, to form an active silicone intermediate. This intermediate can react with a variety of electrophilics, such as aldides, ketones, halogenated hydrocarbons, etc., to carry out nucleophilic substitution or addition reactions to extend carbon chains and establish carbon-silicon bonds. By this method, organic molecules with silicon functional groups can be formed, which are used in materials chemistry and pharmaceutical chemistry. For example, to prepare silicone polymers with special photoelectric properties, bis (tert-butyl) silyl ether halide is used as the starting material, and through a series of reactions, the desired polymer is obtained.
Third, it is used to prepare siloxane polymers. It can be polymerized into a silicone polymer by condensation reaction with silicon compounds containing hydroxyl groups or alkoxy groups under appropriate conditions. Such polymers have excellent thermal stability, weather resistance, and electrical insulation, and are commonly used in coatings, sealants, lubricants, and other fields. Siloxane polymers made of bis (tert-butyl) silyl ether halide can adjust their structure and properties, and should be required differently. For coatings used in high temperature environments, siloxane polymers made of specific structure bis (tert-butyl) silyl ether halide are used as binders to increase the heat and corrosion resistance of coatings.
What is the synthesis method of bis (tert-butyl) phenyl iodonium chloride?
The synthesis of halide is a key method in organic synthetic chemistry. The method is as follows:
First, an appropriate silane, such as dichlorodi (tert-butyl) silane, is reacted with the corresponding alcohol compound. The reaction needs to be carried out in a suitable solvent, such as anhydrous ether or tetrahydrofuran, to ensure the purity of the reaction environment. And the participation of an appropriate base, such as triethylamine or pyridine, is required to neutralize the hydrogen chloride generated by the reaction and promote the reaction to the right.
When reacting, temperature is also a key factor. Usually at low temperature, such as between 0 ° C and room temperature, the reactants are slowly added dropwise to make the reaction occur smoothly and reduce the generation of side reactions. After the dropwise addition is completed, the temperature can be moderately raised to accelerate the reaction process, but care should be taken not to make the temperature too high to avoid product decomposition or other side reactions.
After the reaction is completed, it needs to be separated and purified. The alkali and the generated salts can be washed with water first, and then the product can be extracted with an organic solvent. Common extractants such as dichloromethane or ethyl acetate. After extraction, the moisture in the organic phase is removed with a desiccant such as anhydrous sodium sulfate, and then the pure bis (tert-butyl) silyl ether halide can be obtained by reduced pressure distillation or column chromatography.
or can be obtained by the reaction of the corresponding silanol with halogenated hydrocarbons. This reaction also needs to be carried out in an appropriate alkali and solvent environment. The control of reaction conditions is similar to the above methods. Careful operation is required, paying attention to factors such as temperature, reactant ratio and reaction time, in order to obtain high yield and high purity target products.
What are the physical properties of bis (tert-butyl) phenyl iodonium chloride?
Bis (tert-butyl) silyl ether halide, its physical properties are as follows:
In terms of view, such substances are mostly colorless to light yellow liquid or solid. This is due to the combination of silicon atoms and tert-butyl in the molecular structure, which affects its aggregation state. Tert-butyl has a large steric resistance, or causes the molecular arrangement to be different, which in turn affects the appearance.
When it comes to the melting point, due to the interaction of silicon group with halogen atom and tert-butyl group, the melting point is also different in different structures. Those with larger halogen atoms or special spatial arrangement of tert-butyl group will increase the intermolecular force and the melting point will be higher; conversely, if the force is weak, the melting point will be lower. Such as some simple bis (tert-butyl) silyl ether chlorides, the melting point may be between -20 ° C and 20 ° C.
In terms of boiling point, the silicon-oxygen bond, the silicon-halogen bond and the tert-butyl group in the molecule contribute significantly. The silicon-oxygen bond has a certain polarity, which increases the intermolecular force, and the tert-butyl group also has a great effect. Generally speaking, those with large relative molecular weight and strong intermolecular force have a higher boiling point. Common such halides have boiling points in the range of 100 ° C to 300 ° C.
In terms of solubility, due to the presence of silicon groups and organic tert-butyl groups, they have good solubility in organic solvents such as toluene, dichloromethane, and ethyl ether. The silicon-based organophilic phase, tert-butyl enhances its affinity in organic solvents; however, the solubility in water is poor, because of its overall hydrophobic structure, the force between water molecules and these substances is weak, making it difficult to dissolve each other.
The density is often closely related to the molecular structure. The relative mass of silicon atoms is relatively large, and halogen atoms also contribute, so its density is usually higher than that of common hydrocarbons. The specific value varies depending on the type of halogen atom and the substitution of silicon groups, and is roughly in the range of 1.0 - 1.5 g/cm ³.
In addition, the volatilization of this type of halide is slightly lower than that of ordinary silicone compounds. This is because tert-butyl steric resistance restricts molecular movement, making it more difficult to volatilize And its refractive index is also affected by the molecular structure, due to the different effects of silicon, halogen and other atoms on light refraction, the refractive index may be between 1.45 and 1.55.
What are the precautions for using bis (tert-butyl) phenyl iodonium chloride?
Bis (tert-butyl) silyl ether alkoxylates are suitable for use and should be paid attention to.
First, this material is sensitive, and it must avoid moisture, heat, and oxygen during storage and transportation. Moisture is easy to cause hydrolysis, which damages its structure and properties, and heat and oxygen can also cause it to change, reduce its effectiveness or generate other reactions. Therefore, it should be placed in a cool, dry, and well-sealed place.
Second, when using it, be sure to precisely control its agent. If the agent is too low, the effect of the difficult-to-reach period will be slowed or incomplete if the amount is small in a certain reaction; if the agent is too high, it can cause fees, and or lead to side reactions, resulting in impurities, which will damage the purity and quality of the product.
Third, the environment should be the most serious. Temperature, pH, etc. can all respond to its effect. If the temperature is too high or low, the speed should be different, or the response should be changed. If the temperature should tend to a certain direction, the temperature shift will be easy to other directions; if the pH is not suitable, it can also disturb the reaction, or inactivate the catalyst, or change the response path. Therefore, the use of detailed research should be adjusted according to the needs of the situation.
Fourth, when used with other agents, be careful. If a certain agent is combined with bis (tert-butyl) silyl ether alkoxylates, it can cause a sudden boil or explosion. Therefore, before using it, check the physical properties carefully, and try a small test first to prove that there is no danger before it can be used.
Fifth, use it at all times. Do not discard it indiscriminately, and dispose of it according to the regulations of chemical waste. Because it may contain toxins or harmful substances, discard the polluted ring indiscriminately, endangering the public. Or recycle it for reuse, or decompose it according to the procedure, so as to reduce the shadow of the ring.
