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What is the main use of 2- (3-chloro-5-iodophenyl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane?
2-%283-chloro-5-iodophenyl%29-4%2C4%2C5%2C5-tetramethyl-1%2C3%2C2-dioxaborolane, its chemical name is 2- (3-chloro-5-iodophenyl) -4,4,5,5-tetramethyl-1,3,2-dioxyboropentyl ring. This compound is mainly used in the field of organic synthesis and plays a key role in the construction of complex organic molecular structures.
It is an important player in carbon-carbon bond formation reactions. Take the Suzuki-Miyaura coupling reaction as an example, which is a classic reaction in organic synthesis chemistry to build carbon-carbon bonds. In this reaction, boron atoms in 2- (3-chloro-5-iodophenyl) -4,4,5,5-tetramethyl-1,3,2-dioxoboronane ring cross-couple with halogenated aromatics or olefins under the action of palladium catalysts and bases to form new carbon-carbon bonds, thereby synthesizing aromatics or olefins with specific structures. Such compounds are widely used in the field of medicinal chemistry, and the synthesis of many drug molecules relies on this reaction to construct key structural fragments to impart specific biological activities and pharmacological properties to drugs.
The compound also has important uses in materials science. For example, when synthesizing organic optoelectronic materials, introducing their structural units into target molecules through related reactions can change the electronic and optical properties of the materials, providing basic materials for the preparation of high-performance organic Light Emitting Diodes (OLEDs), organic solar cells and other optoelectronic devices.
It also plays an indispensable role in the field of total synthesis of natural products. Natural products have complex and diverse structures and unique biological activities. In the total synthesis process, the reaction involving 2- (3-chloro-5-iodophenyl) -4,4,5,5-tetramethyl-1,3,2-dioxyboropentyl ring can accurately construct the specific carbon skeleton and functional group in the natural product molecule, realize the artificial synthesis of natural products, and lay the foundation for the study of its biological activity and the development of new drugs.
What are the synthesis methods of 2- (3-chloro-5-iodophenyl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane
There are two common methods for preparing 2- (3-chloro-5-iodophenyl) -4, 4, 5, 5-tetramethyl-1,3,2-dioxyborolane.
First, 3-chloro-5-iodobrobenzene is used as the starting material. First, 3-chloro-5-iodobrobenzene is reacted with magnesium chips in anhydrous ether or tetrahydrofuran and other inert solvents to prepare Grignard's reagent. This process needs to be carried out in an anhydrous and anaerobic environment. Due to the high activity of Grignard's reagent, it is easy to react with water or oxygen and is deactivated. After the Grignard's reagent is prepared, it is reacted with pinacol borate. In this reaction, pinacol borate is used as a boron source, and the two react to form the target product 2- (3-chloro-5-iodophenyl) -4, 4, 5, 5-tetramethyl-1, 3, 2-dioxyboroamyl ring. After the reaction is completed, regular post-treatment, such as extraction, washing, drying, column chromatography separation and other steps, can obtain a pure product.
Second, 3-chloro-5-iodobromobenzene and bis (pinacol) diboron are used as raw materials, catalyzed by palladium catalysts such as tetra (triphenylphosphine) palladium, etc., in suitable solvents such as 1,4-dioxane or toluene, and an appropriate amount of bases such as potassium carbonate, sodium carbonate, etc. are added to react at a certain temperature. The palladium catalyst can reduce the activation energy of the reaction and promote the reaction. The function of the base is to neutralize the acid generated by the reaction and promote the positive progress of the reaction. After the reaction, the pure 2- (3-chloro-5-iodophenyl) -4, 4, 5, 5-tetramethyl-1, 3, 2-dioxoboran ring was obtained by extraction, washing, drying, column chromatography and other post-treatment operations.
These two methods have their own advantages and disadvantages. The actual preparation needs to be comprehensively considered according to the availability of raw materials, cost, reaction conditions and other factors, and the appropriate one should be selected.
What are the physical properties of 2- (3-chloro-5-iodophenyl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane
2-%283-chloro-5-iodophenyl%29-4%2C4%2C5%2C5-tetramethyl-1%2C3%2C2-dioxaborolane, this is an organic compound. Its physical properties are interesting, let me go into detail.
Looking at its appearance, under normal conditions, it may be a white to off-white solid. This morphological feature is easy to store and use, and it can participate in the reaction in a relatively stable state in many chemical reaction systems.
When it comes to melting point, the melting point is within a certain range due to the interaction between specific atoms and groups in the molecular structure. This melting point value is of great significance for controlling the phase transition and purification process of the compound. By measuring the melting point, its purity can be determined. If impurities exist, the melting point may be offset.
In terms of solubility, it has a certain solubility in common organic solvents, such as dichloromethane and toluene. This property makes it well dispersed in the reaction system, which is conducive to the collision and reaction between molecules. In water, the solubility is low due to the poor matching of molecular polarity and water molecular polarity.
Density is also an important physical property. The density of this compound is similar to that of common organic solvents. In the liquid-liquid reaction system, this density characteristic affects its distribution in the system, which is related to the reaction interface and mass transfer process.
Furthermore, the stability of this compound is quite considerable. Boron-oxygen bonds and the overall structure of the molecule give it relatively stable properties. However, in case of extreme conditions such as strong oxidizing agents, strong acids and bases, the structure may be affected. Therefore, when storing, it is necessary to avoid such substances and choose a dry and cool place to store them properly.
To sum up, 2-%283-chloro-5-iodophenyl%29-4%2C4%2C5%2C5-tetramethyl-1%2C3%2C2-dioxaborolane unique physical properties have far-reaching impact on its application in organic synthesis, materials science and other fields.
What are the chemical properties of 2- (3-chloro-5-iodophenyl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane
2-% 283-chloro-5-iodophenyl% 29-4% 2C4% 2C5% 2C5-tetramethyl-1% 2C3% 2C2-dioxoboropentane, which has unique chemical properties. It contains a boroxy heterocyclic structure, and the boron atom is electron-deficient, resulting in Lewis acidity. It can complex with electron-rich species such as electron-containing lone pair molecules or ions, and undergo coordination reactions. It is used as an electrophilic agent in organic synthesis.
The chlorine and iodine atomic properties of this compound are active. Chlorine atoms can undergo nucleophilic substitution reactions, such as being replaced by nucleophiles such as hydroxyl groups and amino groups, to form new carbon-heteroatom bonds and expand the molecular structure. Iodine atoms are more active. Due to the low bond energy of C-I bonds, they are easy to break. Under metal catalysis, they can participate in a variety of coupling reactions. Like Suzuki coupling, carbon-carbon bonds are generated with boron-containing reagents under the catalysis of metals such as palladium to construct complex aromatic compounds, which are widely used in drug and material synthesis.
The tetramethyl structure in the molecule increases its lipid solubility and affects physical properties. For example, in organic solvents, solubility is better. Spatially, tetramethyl produces a steric resistance effect, which affects the selectivity of the reaction. When the reaction reagents are close to the activity check point, a specific orientation is required to guide the reaction in a specific direction and synthesize special structural products. Overall, these properties make 2-% 283-chloro-5-iodophenyl% 29-4% 2C4% 2C5% 2C5-tetramethyl-1% 2C3% 2C2-dioxaborine-heterocyclopentane significant in the field of organic synthesis.
What is the price range of 2- (3-chloro-5-iodophenyl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane in the market?
I do not have the exact number of "2- (3-chloro-5-iodophenyl) -4,4,5,5-tetramethyl-1,3,2-dioxyboron heterocyclopentane" in the market price range. The market price often varies due to various reasons, such as material source, difficulty in preparation, demand, quality and trading season.
If you want to know the price, you can consult chemical product suppliers and distributors to see their quotations. Or visit the chemical product trading platform to check the transaction price of similar commodities for reference. You can also attend the chemical industry meeting and talk with industry people to find out the approximate price.
Due to the lack of specific market survey data, it is difficult to determine the exact price range. However, according to the general practice of chemical products, those with novel, complicated preparation and high purity are often expensive; those with common and easy preparation may be slightly lower. If you want to get an accurate price, you must investigate it carefully in the current market.