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3-fluoropyridine-5-boronic acid pinacol ester
3-Fluoropyridine-5-boronic acid pinacol ester is a crucial reagent in organic synthesis. It has the following chemical properties:
This substance is solid and stable, but it can also exhibit active reactivity under specific conditions. In its structure, the pyridine ring is linked to the boron ester group, and the pyridine ring is aromatic. Due to the presence of nitrogen atoms, it is weakly basic and can react with acids to form salts. The fluorine atom is attached to the pyridine ring because of its high electronegativity, which causes the distribution of electron cloud density to change, which affects the reactivity and selectivity of the pyridine ring.
The boron atom of the pinacol ester of boric acid has a null orbit and can accept electron pairs, showing Lewis acidity. This structure can participate in a variety of organic reactions, such as the Suzuki-Miyaura coupling reaction. In this reaction, pinacol borate and halogenated hydrocarbons or halogenated hydrocarbons form carbon-carbon bonds under the action of palladium catalysts and bases, which are widely used in the construction of carbon skeletons of complex organic molecules.
In terms of solubility, it is generally soluble in common organic solvents, such as dichloromethane, tetrahydrofuran, N, N-dimethylformamide, etc. This property provides convenience for organic synthesis operations, enabling the reaction to proceed efficiently in homogeneous systems. < Br > In terms of stability, it can be stored for a certain period of time at room temperature and pressure, but it is more sensitive to humidity. Moisture is easy to cause hydrolysis of boric acid esters to generate corresponding boric acids. Therefore, it is necessary to pay attention to moisture protection when storing. It is usually stored in a dry environment or in a container filled with inert gas.
3-Fluoropyridine-5-boronic acid esters exhibit rich chemical properties due to their unique chemical structure and play a key role in the field of organic synthetic chemistry.
What are the common synthesis methods of 3-fluoropyridine-5-boronic acid pinacol ester
The common synthesis methods of 3-fluoropyridine-5-boronic acid pinacol ester are as follows:
First, 3-fluoropyridine is used as the starting material. First, a halogenation reaction is used to introduce a halogen atom (such as a bromine atom) at the 5-position of the pyridine ring, which can be achieved by reacting with a brominating reagent (such as N-bromosuccinimide, etc.) under appropriate reaction conditions. Subsequent metallization reactions are carried out, such as the use of reagents such as butyl lithium, to lithium the halogenated 3-fluoropyridine to generate a corresponding lithium reagent. Then let the lithium reagent react with borate esters (such as pinacol borate), and the borate pinacol ester group can be introduced to obtain the target product 3-fluoropyridine-5-boronic acid pinacol ester. This process requires strict control of reaction conditions, such as reaction temperature, reagent dosage, etc., to ensure the smooth progress of the reaction and the purity of the product.
Second, a palladium-catalyzed coupling reaction strategy can be used. Using pyridine derivatives and boric acid pinacol esters containing suitable substituents as raw materials, under the action of palladium catalysts (such as tetra (triphenylphosphine) palladium, etc.), an appropriate amount of base (such as potassium carbonate, etc.) is added, and the reaction is carried out in appropriate solvents (such as toluene, dioxane, etc.). During the reaction process, the palladium catalyst can activate the substrate molecules and promote their coupling reaction, so as to introduce the boric acid pinacol ester group at a specific position in the pyridine ring, thereby obtaining 3-fluoropyridine-5-boronic acid pinacol esters. This method requires relatively mild reaction conditions, but the amount of catalyst and other reagents needs to be precisely controlled to optimize the reaction yield.
3-fluoropyridine-5-boronic acid pinacol ester is used in which areas
3-Fluoropyridine-5-boronic acid pinacol ester, which is useful in many fields. In the field of medicinal chemistry, it is often a key building block for the synthesis of delicate drug molecules. The unique properties of the structure of the gainpyridine ring and boron ester can participate in a variety of chemical reactions, helping to build molecular structures with specific biological activities. Taking the creation of antibacterial drugs as an example, chemists use 3-fluoropyridine-5-boronic acid pinacol ester skillfully, and modify it through multiple steps to give the target molecule the ability to efficiently bind to key bacterial targets, thus achieving the effect of inhibiting bacterial growth and reproduction.
In the field of materials science, it also has extraordinary performance. In the synthesis of organic optoelectronic materials, it can be introduced as an important structural unit to improve the electronic transport and optical properties of materials. For example, when preparing organic Light Emitting Diode (OLED) materials, the conjugate system that the compound participates in can optimize the luminous efficiency and stability of the material, so that the OLED device presents more brilliant colors and longer service life.
Furthermore, in the field of agricultural chemistry, it may become a raw material for the synthesis of new pesticides. After rational design and reaction, pesticide varieties with high selectivity, low toxicity and environmental friendliness to pests can be derived. With its unique chemical structure, it precisely acts on the specific physiological processes of pests, effectively prevents and controls pests and diseases, and reduces the adverse effects on the environment and non-target organisms.
In summary, 3-fluoropyridine-5-boronic acid pinacol ester has shown important application value in many fields such as medicine, materials, and agricultural chemistry, providing a powerful chemical tool for innovation and development in various fields.
What is the market price of 3-fluoropyridine-5-boronic acid pinacol ester
The market price of 3-fluoropyridine-5-boronic acid pinacol ester is difficult to determine. Due to the complex market conditions, the price moves with the wind and is influenced by various factors.
The first to bear the brunt is the state of supply and demand. If there are many people who want it, and the supply is small, the price will increase; on the contrary, if the supply exceeds the demand, the price may be downward. When the chemical industry is booming, many pharmaceutical companies and chemical companies have a surge in demand for boron-containing compounds. If 3-fluoropyridine-5-boronic acid pinacol ester is suitable for emerging drug development or special chemical synthesis, the demand will rise, and the price will follow.
Furthermore, the price of raw materials also affects the whole body. The market price of raw materials for the preparation of this compound, such as fluoropyridine derivatives and pinacol, rises and falls, which is directly related to the cost of the finished product. The price of raw materials is high, and in order to ensure profitability, the price of the finished product will increase.
The difficulty of the process and the scale of production should not be underestimated. If the preparation process is complicated, high-end equipment and exquisite technology are required, and the cost will be high and the price will not be cheap. However, if the production scale can be expanded, the unit cost may be reduced by leveraging the scale effect, and the price may also be lowered.
Regional differences also affect the price. In different places, the price may vary due to different transportation costs, tax policies, and the degree of market competition. In prosperous cities, the market competition is intense, or the price is low due to small profits but quick turnover; in remote places, the transportation cost is high, or the price is high.
To sum up, in order to know the exact market price of 3-fluoropyridine-5-boronic acid pinacol ester, it is necessary to observe the market supply and demand, raw material prices, production conditions and regional factors in real time in order to obtain a more accurate price.
What are the storage conditions for 3-fluoropyridine-5-boronic acid pinacol ester?
3-Fluoropyridine-5-boronic acid pinacol ester, which is a commonly used reagent in organic synthesis. Its storage conditions are quite critical, which is related to the stability and quality of the substance.
The cap is sensitive to moisture due to its borate ester structure. Moisture is prone to hydrolysis of borate esters, which affects its chemical activity and purity. Therefore, the first priority when storing is to maintain a dry environment. It should be stored in a dryer, or in a sealed container filled with inert gas, such as a nitrogen environment, which can effectively isolate external water vapor.
Furthermore, temperature is also an important factor. Generally speaking, a low temperature environment is more conducive to its preservation. Storage temperatures are generally recommended to be between -20 ° C and 0 ° C. Low temperatures can slow down molecular movement, reduce the rate of chemical reactions, and inhibit possible decomposition or metamorphosis reactions.
In addition, light may also affect them. Some organic compounds are prone to photochemical reactions under light conditions. Therefore, they should be stored in a dark place, such as in a brown bottle, or in a dark storage cabinet.
Store 3-fluoropyridine-5-boronic acid pinacol ester in a dry, low temperature and dark environment, so as to ensure that it maintains good chemical properties and purity for a long time for organic synthesis experiments.