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What are the chemical properties of 5-Fluoro-2-Methylbenzeneboronic Acid?
5-Fluoro-2-methylphenylboronic acid, its shape is like a powder and its color is white. This is a commonly used reagent in organic synthesis, and plays a key role in the formation of carbon-carbon bonds and carbon-heteroatomic bonds.
In terms of its physical properties, the melting point is within a specific range, and the specific value varies depending on the measurement conditions. Under normal temperature and pressure, it is quite stable, and it may be dangerous in case of hot topics, open flames or strong oxidizing agents.
In terms of its chemical properties, it has the typical characteristics of boric acid. The boric acid group can react with a variety of compounds, and the common ones can react with alcohols to form borate esters. In case of alkaline substances, it is easy to form borates. Especially important, in transition metal catalyzed reactions, 5-fluoro-2-methylphenylboronic acid can be coupled with halogenated aromatics or olefins, which is an important means to construct complex organic molecular structures.
Because of its fluorine and methyl, it endows the compound with unique electronic effects and steric hindrances. Fluorine atoms have high electronegativity, which can affect the distribution of molecular electron clouds and change the reactivity and selectivity; methyl has a certain degree of electron conductivity and also affects molecular properties. The synergy of the two makes 5-fluoro-2-methylphenylboronic acid show special value in the field of organic synthesis, providing an effective tool for the creation of novel organic materials, drug molecules, etc.
What are the main uses of 5-Fluoro-2-Methylbenzeneboronic Acid?
5-Fluoro-2-methylphenylboronic acid, a compound with a wide range of uses in the field of organic synthesis. Its main uses are roughly as follows.
First, in the field of medicinal chemistry, it is often used as a key building block for the construction of various drug molecules. Due to the unique electronic properties and reactivity of boron atoms, the introduction of boron-containing structures can significantly change the physicochemical properties, biological activities and metabolic properties of drug molecules. By interacting with specific targets, the affinity between drugs and receptors can be enhanced, and the efficacy can be improved. For example, in the development of new therapeutic drugs for specific diseases, 5-fluoro-2-methylphenylboronic acid can be used as a core structural unit to design and synthesize highly selective and potent drug lead compounds through a series of organic reactions, splicing with other active fragments, laying the foundation for new drug development.
Second, it also plays an important role in the field of materials science. It can participate in the preparation of functional organic materials, such as optoelectronic materials. By reacting with other organic conjugated units, polymers or small molecule materials with special optical and electrical properties are constructed. Such materials may exhibit excellent fluorescence properties, charge transport capabilities, etc., and have great application potential in the field of organic Light Emitting Diodes (OLEDs), organic solar cells and other optoelectronic devices, which help to improve the performance and efficiency of the devices.
Third, in the field of organic synthetic chemistry, as an important organic boron reagent, it is widely used in various coupling reactions. For example, in the Suzuki-Miyaura coupling reaction, 5-fluoro-2-methylphenylboronic acid can be coupled with halogenated aromatics or alkenyl halides under the action of palladium catalysts and bases to form carbon-carbon bonds efficiently. This reaction condition is mild and highly selective, and can be used to synthesize aromatic derivatives with complex structures, providing an extremely effective method for organic synthesis chemists to form carbon-carbon bonds, assisting in the synthesis of natural products, organic functional molecules, and fine chemicals, etc., greatly expanding the boundaries and possibilities of organic synthesis.
What are the synthetic methods of 5-Fluoro-2-Methylbenzeneboronic Acid?
There are various ways to prepare 5-fluoro-2-methylphenylboronic acid.
First, halogenated aromatics are used as starting materials. Take 5-fluoro-2-methylbromobenzene or 5-fluoro-2-methylchlorobenzene first, and react with alkyl lithium reagents such as n-butyllithium or isopropyl lithium in a low temperature environment, such as minus 78 degrees Celsius, in an anhydrous ether or tetrahydrofuran ether solvent. This step is a lithium halogen exchange reaction to generate the corresponding aryl lithium intermediate. Subsequently, the intermediate is slowly dropped into a borate ester, such as trimethyl borate or triisopropyl borate, to maintain a low temperature reaction for a period of time. After the reaction is completed, a dilute acid, such as dilute hydrochloric acid or dilute sulfuric acid, is hydrolyzed to obtain 5-fluoro-2-methylphenylboronic acid. This process requires strict anhydrous and oxygen-free to prevent the product from being impure due to the reaction of aryl lithium intermediates with water and oxygen.
Second, the inverse idea of Suzuki coupling reaction can be used. Boron-containing substrates can be prepared first, and then other groups can be removed to obtain the target product. For example, selecting a suitable phenylboronic acid derivative with a protective group, and controlling the halogenated aromatic hydrocarbon derivative containing 5-fluoro-2-methyl, in the presence of a palladium catalyst, such as tetra (triphenylphosphine) palladium (0), and a base, such as potassium carbonate, sodium carbonate, etc., in an organic solvent, such as toluene, dioxane and water, heating the reaction. After the intermediate product is formed, the excess group is removed through a specific deprotection step to obtain 5-fluoro-2-methylphenylboronic acid. The key to this approach lies in the selection of the protective group and the control of the removal conditions. It is necessary to ensure that the protective group is stable during the reaction process and can be removed smoothly under suitable conditions.
Third, the Grignard reagent method. Take 5-fluoro-2-methyl halobenzene, react with magnesium chips in anhydrous ether or tetrahydrofuran to make Grignard reagent. This process requires no water and can be heated slightly when initiating the reaction. The prepared Grignard reagent is then reacted with borate ester, and then hydrolyzed with dilute acid to finally obtain 5-fluoro-2-methylphenylboronic acid. The Grignard reagent method requires attention to the reaction temperature, the quality of magnesium chips and the drying degree of the solvent, which will all affect the formation and reaction effect of Grignard reagent.
5-Fluoro-2-Methylbenzeneboronic Acid to pay attention to when storing and transporting
5-Fluoro-2-methylphenylboronic acid, this is a commonly used reagent in organic synthesis. When storing and transporting, it is necessary to pay attention to many key points.
Let's talk about storage first. Because of its active nature, it is easy to react with other substances, so it should be stored in a dry, cool and well-ventilated place. Do not place it in a high temperature or humid place to prevent it from deteriorating. It should be packed in a sealed container to avoid contact with air. Because of the moisture and oxygen in the air, it may react with it and cause it to fail. And it should be stored separately from oxidants, acids, bases and other substances to prevent danger caused by mutual reaction. The storage area should also be equipped with corresponding emergency treatment equipment and suitable containment materials for emergencies.
As for transportation, it is also not to be taken lightly. It is necessary to ensure that the packaging is intact to prevent its leakage. The transportation process must be kept away from fire and heat sources, and the transportation vehicle should also be equipped with the corresponding variety and quantity of fire-fighting equipment and leakage emergency treatment equipment. During driving, it should be protected from exposure to the sun, rain and high temperature. When loading and unloading, it should be lightly loaded to prevent damage to the packaging and containers. Transportation should be carried on the specified route, and do not stop in residential areas and densely populated areas. In this way, the safety of 5-fluoro-2-methylphenylboronic acid during storage and transportation can be ensured, so that its properties can be stabilized for subsequent use in organic synthesis.
What is the market price of 5-Fluoro-2-Methylbenzeneboronic Acid?
5-Fluoro-2-methylphenylboronic acid, this product is in the market, and its price varies for many reasons.
First, the purity of the quality is the main reason. If the purity is extremely high and almost flawless, it is suitable for high-end scientific research experiments, and its price is high. Because of the difficulty of purification and the labor cost of consumables, the price is often high, up to hundreds of gold per gram. On the contrary, the purity is slightly lower, and it is only used for general industrial synthesis. Its price is cheap, per gram or tens of gold.
The second time, the purchase quantity is also the key to the price. If the purchase quantity is huge, the merchant often gives discounts in order to promote sales, and the unit price decreases. If you buy hundreds of grams or even thousands of grams in bulk, the price per gram is higher than that of sporadic purchases, or you can reduce the price by tens of gold.
Furthermore, the supply and demand of the city determine the price. If there are many people who need it at a certain time, but the supply is limited, the price will rise; if the supply exceeds the demand, the merchant will sell the goods, and the price may decline.
Moreover, the price varies from the producer to the source. Well-known large factories have excellent craftsmanship and strict quality control, and their prices may be high; small factories produce products, although the price is low, the quality may be difficult to compare with large factories. And if the source is far away, the transportation cost will increase, which will also cause the price to rise.
Overall, the market price of 5-fluoro-2-methylphenylboronic acid, if purchased sporadically and with high purity, is 200 to 500 gold per gram; if purchased in bulk and the purity is suitable for ordinary industry, it is 30 to 80 gold per gram. However, the market situation changes, this is only an approximate price, and the actual price depends on the specific situation.