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What are the chemical properties of 4-Bromo-3-Fluorobenzeneboronic Acid?
4-Bromo-3-fluorophenylboronic acid is an important intermediate in organic synthesis. It has unique chemical properties and plays a key role in many chemical reactions.
In terms of its acidity, the phenylboronic acid structure contains boron atoms. Due to the outer electronic structure of boron atoms, it can accept electron pairs and exhibit a certain Lewis acidity. This acidity allows it to react with electron-rich species, such as forming coordination bonds with compounds with solitary pairs of electrons such as nitrogen and oxygen, and then catalyzing or participating in specific organic reactions.
The halogen atoms of 4-bromo-3-fluorophenylboronic acid (bromine and fluorine) also give it special reactivity. Bromine atoms are relatively active. In the nucleophilic substitution reaction, they are easily replaced by various nucleophilic reagents to realize the functional group transformation on the benzene ring. For example, when reacted with nucleophilic reagents such as alkoxides and mercaptan salts, corresponding ethers or thioether compounds can be generated. The introduction of fluorine atoms, although it has high electronegativity, high carbon-fluorine bond energy, and slightly lower reactivity than bromine atoms, significantly affects the electron cloud distribution and spatial structure of molecules, and then changes the physical and chemical properties of molecules. In some reactions, fluorine atoms can enhance the lipophilicity of molecules, affecting the reaction selectivity and the biological activity of products.
Furthermore, the benzene ring structure provides a conjugated system, which makes the molecule stable and can affect the reactivity of the substituents on the benzene ring through electron delocalization. The substituents at different positions interact with each other, resulting in a diversity of reaction check points and reactivity of the whole molecule. In the process of arylation, the phenylboronic acid part can be coupled with other aryl halides or alkenes and other substrates under suitable catalysts and reaction conditions to construct more complex organic molecular structures, which are widely used in drug synthesis, materials science and other fields.
What are the main uses of 4-Bromo-3-Fluorobenzeneboronic Acid?
4-Bromo-3-fluorophenylboronic acid is an important reagent in organic synthesis. It has a wide range of uses and often plays a key role in the formation of carbon-carbon bonds.
First, in the Suzuki coupling reaction, 4-bromo-3-fluorophenylboronic acid can efficiently form carbon-carbon bonds with halogenated aromatics or olefins under the action of palladium catalysts and bases, thereby synthesizing many biphenyl compounds with specific structures. Such compounds are widely used in the fields of medicinal chemistry and materials science. For example, when creating new anti-cancer drugs, this reaction can be used to build a key molecular skeleton.
Second, in the process of synthesizing complex natural products or bioactive molecules, 4-bromo-3-fluorophenylboronic acid can be used as a key intermediate to precisely construct the required complex structure through multi-step reactions. It can participate in a series of nucleophilic substitution, addition and other reactions, providing an effective way for the synthesis of compounds with specific spatial structures and functional group arrangements.
Third, in the field of materials, polymers or functional materials prepared by its participation in the reaction may have unique photoelectric properties. For example, when preparing organic Light Emitting Diode (OLED) materials, the introduction of structural units containing the boric acid can adjust the material's luminous wavelength, efficiency and other properties, thereby meeting the needs of different display technologies.
Fourth, in the study of organic synthesis methodology, 4-bromo-3-fluorophenylboronic acid is often used to explore new reaction pathways and catalytic systems. Researchers explore more efficient and green synthesis strategies by changing reaction conditions and matching different ligands, promoting the development of organic synthesis chemistry.
What are the synthesis methods of 4-Bromo-3-Fluorobenzeneboronic Acid?
The synthesis of 4-bromo-3-fluorophenylboronic acid is an important topic in organic synthetic chemistry. There are many methods, each with its own advantages and disadvantages, and should be carefully selected according to actual needs and conditions.
One of them can be started from 4-bromo-3-fluorobromobenzene. First, 4-bromo-3-fluorobromobenzene reacts with metal magnesium to form Grignard reagents. This reaction needs to be carried out in a harsh environment without water and oxygen, using ether or tetrahydrofuran as a solvent, stirring at low temperature, so that the magnesium strips can fully react with halogenated aromatics to form active Grignard reagents. Then, the Grignard reagent is reacted with borate ester and hydrolyzed to obtain 4-bromo-3-fluorophenylboronic acid. The advantage of this approach is that the raw materials are relatively easy to obtain and the reaction steps are relatively clear; however, the requirements for the reaction environment are extremely high, and the anhydrous and anaerobic operation increases the difficulty and cost of the experiment.
Second, the Suzuki reaction strategy can be used. 4-bromo-3-fluorohalobenzene and pinacol biborate are used as raw materials to react in the presence of a palladium catalyst and a base. Commonly used palladium catalysts such as tetra (triphenylphosphine) palladium, and the base can be potassium carbonate, sodium carbonate, etc. This reaction condition is relatively mild and However, palladium catalysts are expensive, and the post-reaction treatment requires fine operation to remove the catalyst residue, so as not to affect the purity of the product.
Others use 4-bromo-3-fluoroaniline as the starting material. It is first diazotized, and then reacted with boric acid or borate ester. The diazotization reaction needs to be carried out in a low temperature and strong acid environment, and sodium nitrite is used as the reagent to generate diazonium salts. This diazonium salt is active, and the target product can be obtained by reacting with boric acid or borate ester. Although this method is a little complicated, the raw materials are widely sourced and the cost may be reduced. However, the risk of diazotization reaction is high, and the reaction conditions need to be strictly controlled to ensure safety.
All synthesis methods have their own strengths and weaknesses. In actual synthesis, many factors such as raw material cost, reaction conditions, product purity and yield must be considered, the advantages and disadvantages must be weighed, and the best one can be used to achieve the purpose of efficient synthesis of 4-bromo-3-fluorophenylboronic acid.
What are the precautions for 4-Bromo-3-Fluorobenzeneboronic Acid in storage and transportation?
4-Bromo-3-fluorophenylboronic acid is a commonly used reagent in organic synthesis. When storing and transporting, many matters must be paid attention to.
Storage first. This substance should be placed in a dry, cool and well-ventilated place. Because of its certain chemical activity, it is easy to cause it to deteriorate in a humid environment. If moisture intrudes, or causes reactions such as hydrolysis, its purity and activity are damaged. Therefore, it should be contained in a sealed container to avoid contact with water vapor. And the temperature must also be controlled. Excessive temperature or promote its decomposition, generally not exceeding 25 ° C. In some cases, it may need to be refrigerated and stored between about 2-8 ° C.
Then transport. During transportation, it is important to be shockproof and anti-collision. Because of its shape or solid powder, violent vibration or damage to the package, causing it to be exposed to the outside. The packaging must be strong, and suitable packaging materials should be selected, such as sealed glass bottles or plastic bottles, with buffer material protection. At the same time, the transportation environment should also be dry, avoiding high temperature and high humidity. If long-distance transportation, it is necessary to ensure that the temperature is stable, and temperature-controlled transportation equipment can be used.
In short, the storage and transportation of 4-bromo-3-fluorophenylboronic acid must be careful to treat environmental factors such as humidity and temperature, and pay attention to the stability of the packaging, so as to ensure its quality and performance, so as to prepare for organic synthesis and other purposes.
What is the market price of 4-Bromo-3-Fluorobenzeneboronic Acid?
4-Bromo-3-fluorophenylboronic acid, the price of this product in the market often changes due to differences in quality, supply and demand, and purchase quantity. In the past, the prices of all kinds of materials fluctuated with market conditions, and the same is true.
If it is about the general, in ordinary market shops, the price of small purchases may range from tens of yuan to hundreds of yuan per gram. If the demand is quite large, or negotiate with suppliers, the price may be discounted due to the increase in quantity.
However, looking at the changes in the market, the production of raw materials, the progress of craftsmanship, and the regulations of the government can all cause the price to fluctuate. If the raw materials are abundant, the production is convenient, and the price may decline; if the raw materials are scarce, the production is complicated, and the demand is greater than the supply, the price will rise.
For those who are also in the market, each has its own price, or the price difference is also obvious due to the difference in brand, purity, and service. To get the actual price, you must consult various suppliers in detail, compare their advantages and disadvantages, and measure their cost performance before you can know their appropriate value.