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2-Chloro-5-Formylbenzeneboronic Acid
Linshang Chemical
|
HS Code |
841612 |
| Chemical Formula | C7H6BClO3 |
| Molar Mass | 184.39 g/mol |
| Appearance | Solid (usually white to off - white) |
| Solubility In Water | Poorly soluble |
| Solubility In Organic Solvents | Soluble in some polar organic solvents like DMSO, THF |
| Pka | Typical for boronic acids (around 8 - 9) |
| Boiling Point | Decomposes before boiling |
| Melting Point | 145 - 150 °C (approximate, may vary) |
| Stability | Sensitive to moisture, should be stored dry |
As an accredited 2-Chloro-5-Formylbenzeneboronic Acid factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | 100g of 2 - chloro - 5 - formylbenzeneboronic acid in a sealed, labeled container. |
| Storage | 2 - Chloro - 5 - formylbenzeneboronic acid should be stored in a cool, dry place away from heat and ignition sources. Keep it in a tightly - sealed container to prevent contact with moisture, as boronic acids can react with water. Store it separately from incompatible substances like strong oxidizing agents and bases to avoid chemical reactions that could degrade the compound. |
| Shipping | 2 - chloro - 5 - formylbenzeneboronic acid, being a chemical, is shipped in well - sealed, corrosion - resistant containers. It's handled with care, following hazardous material shipping regulations to prevent spills and ensure safe transportation. |
Competitive 2-Chloro-5-Formylbenzeneboronic Acid prices that fit your budget—flexible terms and customized quotes for every order.
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What is the chemical structure of 2-chloro-5-formylbenzeneboronic Acid?
2-Chloro-5-formylphenylboronic acid (2-chloro-5-formylbenzeneboronic Acid) has a unique chemical structure. In this compound, the benzene ring is the backbone, just like the backbone of the building, supporting the entire structure. On the benzene ring, the chlorine atom is on one side with the formyl group and the boric acid group.
The chlorine atom, with its unique electronic effect, affects the electron cloud distribution of the benzene ring. Its electron-absorbing properties reduce the electron cloud density of the ortho and para-sites, which in turn affects the chemical activity and reaction characteristics of this compound.
formyl (-CHO), like a dancer, adds a different kind of activity to the molecule. Its carbon-oxygen double bond, which is not only electron-rich unsaturated, but also makes carbonyl carbon electrophilic, easy to react with nucleophiles, and is often a key activity check point in many organic synthesis reactions.
Boric acid group (-B (OH) -2) is also indispensable. The electron-deficient nature of boron atoms makes boric acid groups can be used as Lewis acids under specific conditions to participate in various catalytic reactions or form coordination bonds with other compounds. At the same time, boric acid groups also play an important role in the formation of carbon-carbon bonds and carbon-heteroatomic bonds, such as the Suzuki-Miyaura coupling reaction.
The chemical structure of 2-chloro-5-formylphenylboronic acid, due to the ingenious arrangement of these functional groups on the benzene ring, endows it with unique physical and chemical properties, and has high research and application value in organic synthesis, pharmaceutical chemistry and other fields.
The chlorine atom, with its unique electronic effect, affects the electron cloud distribution of the benzene ring. Its electron-absorbing properties reduce the electron cloud density of the ortho and para-sites, which in turn affects the chemical activity and reaction characteristics of this compound.
formyl (-CHO), like a dancer, adds a different kind of activity to the molecule. Its carbon-oxygen double bond, which is not only electron-rich unsaturated, but also makes carbonyl carbon electrophilic, easy to react with nucleophiles, and is often a key activity check point in many organic synthesis reactions.
Boric acid group (-B (OH) -2) is also indispensable. The electron-deficient nature of boron atoms makes boric acid groups can be used as Lewis acids under specific conditions to participate in various catalytic reactions or form coordination bonds with other compounds. At the same time, boric acid groups also play an important role in the formation of carbon-carbon bonds and carbon-heteroatomic bonds, such as the Suzuki-Miyaura coupling reaction.
The chemical structure of 2-chloro-5-formylphenylboronic acid, due to the ingenious arrangement of these functional groups on the benzene ring, endows it with unique physical and chemical properties, and has high research and application value in organic synthesis, pharmaceutical chemistry and other fields.
What are the main uses of 2-chloro-5-formylbenzeneboronic Acid?
2-Chloro-5-formylphenylboronic acid, this substance has a wide range of uses and is very useful in the field of organic synthesis.
First, it can be used as a key building block for the construction of complex organic molecules. The way of organic synthesis is like building a delicate castle, requiring all kinds of cornerstones. 2-Chloro-5-formylphenylboronic acid can participate in many reactions due to its unique structure, such as the Suzuki coupling reaction. This reaction is like a chemical bridge that can connect different organic fragments. In this reaction, 2-chloro-5-formylphenylboronic acid can be cleverly combined with substrates such as halogenated aromatics or olefins under the action of palladium catalyst to form new carbon-carbon bonds, which provides the possibility for the synthesis of complex structures such as polyaryl compounds and conjugated olefin compounds. These compounds are of great significance in the fields of materials science and medicinal chemistry.
Second, it is also of great value in the development of drugs. The design and synthesis of drug molecules often require precise construction of specific structures. 2-chloro-5-formylphenylboronic acid can be used as a key raw material for the modification of lead compounds. By derivatization, adding different functional groups, changing the physical and chemical properties and biological activities of the molecule, and then screening compounds with potential pharmacological activities, providing direction for the creation of new drugs.
Third, in the field of materials science, it makes a difference. In the synthesis of optoelectronic materials, it can be used to participate in reactions to prepare materials with special optoelectronic properties. For example, synthesizing organic semiconductor materials with specific luminescent properties or electrical conductivity, such materials may play an important role in devices such as organic Light Emitting Diode (OLED) and organic solar cells, helping to improve device performance.
First, it can be used as a key building block for the construction of complex organic molecules. The way of organic synthesis is like building a delicate castle, requiring all kinds of cornerstones. 2-Chloro-5-formylphenylboronic acid can participate in many reactions due to its unique structure, such as the Suzuki coupling reaction. This reaction is like a chemical bridge that can connect different organic fragments. In this reaction, 2-chloro-5-formylphenylboronic acid can be cleverly combined with substrates such as halogenated aromatics or olefins under the action of palladium catalyst to form new carbon-carbon bonds, which provides the possibility for the synthesis of complex structures such as polyaryl compounds and conjugated olefin compounds. These compounds are of great significance in the fields of materials science and medicinal chemistry.
Second, it is also of great value in the development of drugs. The design and synthesis of drug molecules often require precise construction of specific structures. 2-chloro-5-formylphenylboronic acid can be used as a key raw material for the modification of lead compounds. By derivatization, adding different functional groups, changing the physical and chemical properties and biological activities of the molecule, and then screening compounds with potential pharmacological activities, providing direction for the creation of new drugs.
Third, in the field of materials science, it makes a difference. In the synthesis of optoelectronic materials, it can be used to participate in reactions to prepare materials with special optoelectronic properties. For example, synthesizing organic semiconductor materials with specific luminescent properties or electrical conductivity, such materials may play an important role in devices such as organic Light Emitting Diode (OLED) and organic solar cells, helping to improve device performance.
What are the synthesis methods of 2-chloro-5-formylbenzeneboronic Acid?
The synthesis method of 2-chloro-5-formylphenylboronic acid has always been the most important in the field of organic synthesis. The methods vary, and the details are described below.
First, 2-chloro-5-methylbenzoic acid is used as the starting material. First, it is reacted with a strong oxidant, such as potassium dichromate-sulfuric acid system, in the state of heating reflux, and methyl groups can be oxidized to carboxyl groups to obtain 2-chloro-5-carboxybenzoic acid. Then, this product interacts with the sodium borohydride-iodine system to reduce carboxyl groups to hydroxymethyl groups. Then manganese dioxide is used as the oxidant, and in a suitable solvent, hydroxymethyl is oxidized to formyl group to obtain 2-chloro-5-formylbenzoic acid. Finally, it reacts with butyllithium and trimethyl borate in sequence, and is hydrolyzed to obtain 2-chloro-5-formylphenylboronic acid.
Second, 2-chloro-1-methyl-4-nitrobenzene is used as the starting material. First, the nitro group is reduced to the amino group in the iron powder-hydrochloric acid system to obtain 2-chloro-4-amino-1-methylbenzene. This product is reacted with sodium nitrite-hydrochloric acid system at low temperature to obtain diazonium salt. Then the diazonium salt is reacted with cuprous chloride to replace the diazonium group with chlorine to obtain 2-chloro-1-chloromethyl-4-chlorobenzene. The chlorine of chloromethyl is replaced by sodium cyanide to obtain 2-chloro-5-cyanobenzene. The cyanyl group is hydrolyzed as a carboxyl group by acid catalysis, and then reduced and oxidized, as described above, to obtain 2-chloro-5-formylbenzoic acid, which is finally converted into the target product 2-chloro-5-formylphenylboronic acid according to the previous method.
Third, 2-chlorobenzaldehyde is used as the starting material. First, the hydroxyaldehyde condensation reaction is carried out with formaldehyde under alkaline conditions to obtain 2-chloro-5- (hydroxymethyl) benzaldehyde. After oxidation, boronation and other steps, 2-chloro-5-formylphenylboronic acid can also be obtained.
All synthesis methods have their own advantages and disadvantages. The ease of availability of raw materials, the difficulty of reaction conditions, and the yield are all factors to be considered. At the time of synthesis, the advantages and disadvantages should be weighed according to the actual situation, and the optimal method should be selected to achieve the purpose of efficient preparation of 2-chloro-5-formylphenylboronic acid.
First, 2-chloro-5-methylbenzoic acid is used as the starting material. First, it is reacted with a strong oxidant, such as potassium dichromate-sulfuric acid system, in the state of heating reflux, and methyl groups can be oxidized to carboxyl groups to obtain 2-chloro-5-carboxybenzoic acid. Then, this product interacts with the sodium borohydride-iodine system to reduce carboxyl groups to hydroxymethyl groups. Then manganese dioxide is used as the oxidant, and in a suitable solvent, hydroxymethyl is oxidized to formyl group to obtain 2-chloro-5-formylbenzoic acid. Finally, it reacts with butyllithium and trimethyl borate in sequence, and is hydrolyzed to obtain 2-chloro-5-formylphenylboronic acid.
Second, 2-chloro-1-methyl-4-nitrobenzene is used as the starting material. First, the nitro group is reduced to the amino group in the iron powder-hydrochloric acid system to obtain 2-chloro-4-amino-1-methylbenzene. This product is reacted with sodium nitrite-hydrochloric acid system at low temperature to obtain diazonium salt. Then the diazonium salt is reacted with cuprous chloride to replace the diazonium group with chlorine to obtain 2-chloro-1-chloromethyl-4-chlorobenzene. The chlorine of chloromethyl is replaced by sodium cyanide to obtain 2-chloro-5-cyanobenzene. The cyanyl group is hydrolyzed as a carboxyl group by acid catalysis, and then reduced and oxidized, as described above, to obtain 2-chloro-5-formylbenzoic acid, which is finally converted into the target product 2-chloro-5-formylphenylboronic acid according to the previous method.
Third, 2-chlorobenzaldehyde is used as the starting material. First, the hydroxyaldehyde condensation reaction is carried out with formaldehyde under alkaline conditions to obtain 2-chloro-5- (hydroxymethyl) benzaldehyde. After oxidation, boronation and other steps, 2-chloro-5-formylphenylboronic acid can also be obtained.
All synthesis methods have their own advantages and disadvantages. The ease of availability of raw materials, the difficulty of reaction conditions, and the yield are all factors to be considered. At the time of synthesis, the advantages and disadvantages should be weighed according to the actual situation, and the optimal method should be selected to achieve the purpose of efficient preparation of 2-chloro-5-formylphenylboronic acid.
What are the physical properties of 2-chloro-5-formylbenzeneboronic Acid?
2-Chloro-5-formylphenylboronic acid is a key intermediate in the field of organic synthesis. According to its physical properties, under room temperature and pressure, this substance is mostly in solid form. As for the specific appearance, or white to light yellow crystalline powder, this varies slightly due to differences in preparation methods and purity.
When it comes to melting point, it usually falls within a specific range, but the exact value will vary depending on the amount of impurities and test conditions. Generally speaking, the melting point of pure 2-chloro-5-formylphenylboronic acid is relatively clear and stable, which can be used as an important indicator for the identification of this substance.
In terms of solubility, it varies from common organic solvents. In some polar organic solvents, such as dichloromethane, N, N-dimethylformamide (DMF), it often exhibits good solubility, which makes it possible to disperse them uniformly in related organic synthesis reactions, thereby promoting the smooth progress of the reaction. However, in non-polar solvents, such as n-hexane, the solubility is poor.
In addition, the substance is more sensitive to humidity. In humid environments, it may react with water, causing its own structure to change, affecting its chemical activity and stability. Therefore, during storage and use, it is necessary to maintain a dry environment to prevent it from deteriorating and ensure that it can play its intended role in application scenarios such as organic synthesis.
When it comes to melting point, it usually falls within a specific range, but the exact value will vary depending on the amount of impurities and test conditions. Generally speaking, the melting point of pure 2-chloro-5-formylphenylboronic acid is relatively clear and stable, which can be used as an important indicator for the identification of this substance.
In terms of solubility, it varies from common organic solvents. In some polar organic solvents, such as dichloromethane, N, N-dimethylformamide (DMF), it often exhibits good solubility, which makes it possible to disperse them uniformly in related organic synthesis reactions, thereby promoting the smooth progress of the reaction. However, in non-polar solvents, such as n-hexane, the solubility is poor.
In addition, the substance is more sensitive to humidity. In humid environments, it may react with water, causing its own structure to change, affecting its chemical activity and stability. Therefore, during storage and use, it is necessary to maintain a dry environment to prevent it from deteriorating and ensure that it can play its intended role in application scenarios such as organic synthesis.
2-chloro-5-formylbenzeneboronic Acid need to pay attention to when storing and shipping?
2-Chloro-5-formylphenylboronic acid, which is an important reagent in organic synthesis. When storing and transporting, many key points must be paid attention to to to ensure its quality and stability.
First, storage, because of its certain chemical activity, should be stored in a dry place. Moisture can easily cause hydrolysis, which in turn destroys its chemical structure and makes the reagent ineffective. In the warehouse, be sure to keep the air dry and the humidity should be controlled at a low level. And it should be placed in a cool place, never exposed to high temperature and strong light. High temperature will accelerate the process of its chemical reaction, and strong light may also induce luminescent chemical reactions, which will damage its stability. In addition, this reagent needs to be kept away from fire sources and oxidants. Because of its flammability, it is easy to cause violent reactions in case of oxidants, which endangers safety. When storing, it should be placed separately from dangerous items such as fire sources and oxidants, and clearly marked.
As for transportation, the same cannot be ignored. Appropriate packaging materials need to be used to avoid package damage due to vibration and collision during transportation. The packaging should be solid and cushioning to ensure the stability of the reagent. The transportation environment is also crucial. It is necessary to maintain suitable temperature and humidity to avoid extreme conditions. If long-distance transportation, it is necessary to strengthen temperature and humidity monitoring to prevent the deterioration of the reagent. At the same time, transportation personnel also need professional training to be familiar with the characteristics of this reagent and emergency treatment methods. In the event of an unexpected situation such as a leak, it can be responded to quickly and properly to reduce the harm.
In short, the storage and transportation of 2-chloro-5-formylphenylboronic acid requires comprehensive consideration of many factors and strict operation in accordance with regulations to ensure its safety and quality.
First, storage, because of its certain chemical activity, should be stored in a dry place. Moisture can easily cause hydrolysis, which in turn destroys its chemical structure and makes the reagent ineffective. In the warehouse, be sure to keep the air dry and the humidity should be controlled at a low level. And it should be placed in a cool place, never exposed to high temperature and strong light. High temperature will accelerate the process of its chemical reaction, and strong light may also induce luminescent chemical reactions, which will damage its stability. In addition, this reagent needs to be kept away from fire sources and oxidants. Because of its flammability, it is easy to cause violent reactions in case of oxidants, which endangers safety. When storing, it should be placed separately from dangerous items such as fire sources and oxidants, and clearly marked.
As for transportation, the same cannot be ignored. Appropriate packaging materials need to be used to avoid package damage due to vibration and collision during transportation. The packaging should be solid and cushioning to ensure the stability of the reagent. The transportation environment is also crucial. It is necessary to maintain suitable temperature and humidity to avoid extreme conditions. If long-distance transportation, it is necessary to strengthen temperature and humidity monitoring to prevent the deterioration of the reagent. At the same time, transportation personnel also need professional training to be familiar with the characteristics of this reagent and emergency treatment methods. In the event of an unexpected situation such as a leak, it can be responded to quickly and properly to reduce the harm.
In short, the storage and transportation of 2-chloro-5-formylphenylboronic acid requires comprehensive consideration of many factors and strict operation in accordance with regulations to ensure its safety and quality.
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