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4-(Methoxycarbonyl)phenylboronic Acid is a functionalized boronic acid derivative with the chemical formula C₉H₁₁BO₄. It consists of a phenyl ring substituted with a boronic acid group (–B(OH)₂) at the 1-position and a methoxycarbonyl (–COOCH₃) ester group at the 4-position. This structure combines the reactivity of boronic acids with the electron-withdrawing properties of the ester, making it a versatile intermediate in organic synthesis and materials science.
Boronic acids are renowned for their ability to form reversible covalent bonds with diols, such as those in sugars or vicinal diol-containing compounds, under mild conditions. This property underpins their applications in carbohydrate sensing, glycopeptide analysis, and the synthesis of boronate ester-linked polymers. The 4-(methoxycarbonyl)phenyl group introduces additional reactivity, as the ester can be hydrolyzed to a carboxylic acid or used in cross-coupling reactions (e.g., Suzuki-Miyaura coupling) to form C-C bonds, expanding its synthetic utility.
In materials chemistry, this compound serves as a precursor for boronate-functionalized polymers or surfaces, which are exploited in glucose sensors, drug delivery systems, and molecular recognition. The ester group also enables post-functionalization, allowing tuning of solubility, hydrophobicity, or biocompatibility. Its stability under ambient conditions and compatibility with aqueous media further enhance its practicality.
Researchers leverage its dual functionality to design stimuli-responsive materials or probes for biological targets. For instance, the boronic acid can bind diols reversibly, while the ester could be modified to release a cargo or alter the material's properties in response to pH or enzymatic activity.
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Chemical Formula |
C8H9BO4 |
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Exact Mass |
180 |
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Molecular Weight |
180 |
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m/z |
180 (100.0%), 179 (24.8%), 181 (8.7%), 180 (2.1%) |
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Elemental Analysis |
C, 53.39; H, 5.04; B, 6.01; O, 35.56 |
Suzuki-Miyaura Cross-Coupling Reactions
Role: Acts as a boronic acid derivative in palladium-catalyzed Suzuki-Miyaura cross-coupling reactions.
Function: Enables the formation of carbon-carbon bonds between aryl halides and boronic acids, yielding biaryls, heterobiaryls, and other complex organic structures.
Advantage: High functional group tolerance and mild reaction conditions make it ideal for synthesizing drug candidates and advanced materials.
Pharmaceutical Intermediate
Drug Synthesis: Used in the preparation of:
- Anticancer agents (e.g., tyrosine kinase inhibitors).
- Antiviral compounds (e.g., nucleoside analogs).
- Antibiotics (e.g., β-lactamase inhibitors).
Example: Synthesis of ibrutinib (a BTK inhibitor for leukemia) involves boronic acid intermediates for aromatic ring construction.
Polymer and Materials Science
Conjugated Polymers: Incorporated into the synthesis of:
- Polyfluorenes (for OLEDs and organic solar cells).
- Polythiophenes (for conductive polymers and sensors).
Function: Boronic acid groups enable post-polymerization modification via covalent bonding with diols or other functionalized molecules.
Advantage: Enhances solubility, processability, and stability of polymers.
Supramolecular Chemistry and Self-Assembly
Boronate Ester Formation: Reacts with diols to form reversible covalent bonds, useful in:
- Dynamic covalent chemistry (for adaptive materials).
- Self-healing polymers (for coatings and adhesives).
Example: Formation of boronate ester-based hydrogels for drug delivery or tissue engineering.
Chemical Sensors and Detection
Fluorescent Probes: Boronic acid groups selectively bind diols (e.g., glucose, saccharides), enabling:
- Glucose sensors (for diabetes monitoring).
- Bacterial detection (via interactions with peptidoglycan).
Mechanism: Boron-diol complexation induces fluorescence changes or colorimetric signals.
Catalysis and Asymmetric Synthesis
Chiral Ligand: Used in asymmetric catalysis (e.g., in hydroboration or Suzuki reactions) to improve enantioselectivity.
Example: Asymmetric synthesis of chiral alcohols or amines via boronic acid-mediated reactions.
Surface Modification and Functionalization
Boronic Acid-Functionalized Surfaces: Used to immobilize biomolecules (e.g., enzymes, antibodies) for:
- Biosensors (for diagnostics).
- Microarrays (for high-throughput screening).
Advantage: Reversible binding allows for surface regeneration.
Cross-Linking Agents in Hydrogels
Hydrogel Formation: Reacts with diols to form cross-linked networks, useful in:
- Drug delivery systems (for controlled release).
- 3D cell culture scaffolds (for tissue engineering).
Example: Boronate ester-based hydrogels for sustained insulin release.
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Borate ester-based hydrogels are a fascinating class of materials that have garnered significant attention in recent years due to their unique properties and diverse applications. These hydrogels are formed through the cross-linking of polymers using borate esters as the cross-linking agents.
One of the key features of borate ester-based hydrogels is their dynamic and reversible cross-linking nature. The borate ester bonds can form and break under specific conditions, such as changes in pH or the presence of certain ions. This property allows the hydrogels to exhibit self-healing capabilities, enabling them to repair damage and recover their original structure and mechanical properties.
In terms of applications, borate ester-based hydrogels find use in various fields. In biomedicine, they can be utilized as drug delivery systems, where the controlled release of drugs is achieved through the responsive behavior of the hydrogel to environmental stimuli. Additionally, they show promise in tissue engineering, providing a suitable matrix for cell growth and tissue regeneration. In the environmental sector, these hydrogels can be employed for water purification and the removal of heavy metal ions from contaminated water sources. Overall, borate ester-based hydrogels represent a versatile and promising area of research with far-reaching implications.
4-(methoxycarbonyl)phenylboronic acid (methyl 4 - boronobenzoate) can form boronate ester - based hydrogels through specific chemical reactions, and these hydrogels have potential applications in drug delivery and tissue engineering, as detailed below:
Formation mechanism of boronate ester - based hydrogels
- Reaction principle: Boronic acid groups can react with diols to form reversible covalent boronate esters. This reaction is the basis for the formation of boronate ester - based hydrogels. By controlling the reaction conditions and the ratio of reactants, hydrogels with different network structures and properties can be prepared.
- Cross - linking process: When it is mixed with a polymer containing diol groups in an appropriate solvent, the boronic acid groups and diol groups undergo a condensation reaction to form boronate ester bonds, which cross - link the polymer chains to form a three - dimensional hydrogel network.
Applications in drug delivery
- Controlled drug release: The boronate ester bonds in the hydrogels have a certain degree of dynamic reversibility. They can respond to changes in the external environment, such as pH, glucose concentration, etc. This property can be used to achieve controlled drug release. For example, in a slightly acidic tumor microenvironment, the boronate ester bonds may break, leading to the disintegration of the hydrogel and the release of the loaded drugs.
- Improving drug stability: Hydrogels can encapsulate drugs, protecting them from degradation in the physiological environment and improving their stability. 4-methoxycarbonylphenylboronic acid - based boronate ester hydrogels can provide a suitable microenvironment for drugs, extending their half - life in the body.
- Targeted drug delivery: By modifying the surface of the hydrogels or introducing specific targeting ligands, targeted drug delivery to specific tissues or cells can be achieved. For instance, if the hydrogels are designed to target tumor cells, they can accumulate at the tumor site, increasing the local drug concentration and reducing side effects on normal tissues.
Applications in tissue engineering
- Biocompatibility: Boronate ester - based hydrogels formed by 4-methoxycarbonylphenylboronic acid generally have good biocompatibility. They can provide a three - dimensional scaffold for cell adhesion, proliferation, and differentiation, similar to the extracellular matrix in the body.
- Adjustable mechanical properties: The mechanical properties of the hydrogels can be adjusted by changing the cross - linking density, the type of polymers used, and the reaction conditions. This adjustability allows the hydrogels to match the mechanical requirements of different tissues, such as soft tissues like skin and muscle or harder tissues like cartilage and bone.
- Support for tissue regeneration: The hydrogels can serve as a temporary support for tissue regeneration. They can provide a space for cell growth and tissue formation, and gradually degrade as the new tissue grows, being replaced by the body's own tissues.
adverse reaction
4-(methoxycarbonyl)phenylboronic acid (MPBA) is an aromatic compound containing boronic acid and ester groups, with a molecular weight of 179.96 g/mol and a melting point of 120-122 ° C. It is a white to off white crystalline powder at room temperature. As a key reagent in Suzuki coupling reactions, MPBA is widely used in the synthesis of aromatic structural units in drugs, pesticides, and polymer materials. However, during its production, storage, and use, it may be released into the environment or cause human exposure, posing health risks.
Acute Toxicity
Oral toxicity
Animal experimental studies have shown that 4- (methoxycarbonyl) phenylboronic acid, when ingested orally, can cause certain acute toxic effects on experimental animals. Different types of experimental animals may have varying sensitivities to it, but generally exhibit symptoms such as reduced activity, mental fatigue, and loss of appetite at higher doses. As the dosage increases, breathing difficulties, convulsions, and even death may occur. The median lethal dose (LD ₅₀) of this compound fluctuates depending on experimental conditions and animal species, but is usually within a certain range. This suggests that the compound has a certain level of danger when ingested orally and requires strict control of the exposure dose.
Skin Contact Toxicity
When 4- (methoxycarbonyl) phenylboronic acid comes into direct contact with the skin, it may cause skin irritation. Short term exposure may cause discomfort symptoms such as redness, itching, and burning sensation on the skin. In high concentrations or prolonged exposure, it may cause skin damage such as ulcers, erosions, etc. This is because the compound may disrupt the barrier function of the skin, causing damage to skin cells and inflammatory reactions.
Inhalation toxicity
Although 4- (methoxycarbonyl) phenylboronic acid has relatively low volatility at room temperature, certain amounts of aerosols or vapors may be generated during certain operating conditions such as heating, crushing, etc. When the human body inhales air containing this compound, it can cause irritation to the respiratory tract. Mild cases may experience symptoms such as coughing, sputum production, and wheezing, while severe cases may cause respiratory inflammation, pulmonary edema, and affect respiratory function.
Chronic Toxicity
Effects on the liver
Long term exposure to 4- (methoxycarbonyl) phenylboronic acid may cause chronic damage to the liver. The liver is an important metabolic organ in the human body, and after entering the body, this compound may undergo metabolic transformation in the liver. During this process, it may interfere with the normal metabolic function of the liver, leading to damage to liver cells. Animal experiments have found that long-term exposure to a certain dose of this compound can cause pathological changes in the liver of experimental animals, such as swelling, degeneration, and necrosis of liver cells. At the same time, biochemical indicators such as alanine aminotransferase (ALT) and aspartate aminotransferase (AST) in the liver will also increase, indicating damage to liver function.
Effects on the kidneys
The kidney is also one of the target organs for chronic toxicity of 4- (methoxycarbonyl) phenylboronic acid. This compound and its metabolites may be excreted through the kidneys, causing damage to kidney tissue during this process. Long term exposure may lead to damage to renal tubular epithelial cells, affecting the concentration and dilution functions of the kidneys, resulting in symptoms such as proteinuria and hematuria. In severe cases, it may cause a decrease in glomerular filtration function, leading to renal dysfunction.
Effects on the immune system
Long term exposure to 4- (methoxycarbonyl) phenylboronic acid may also have adverse effects on the immune system. It may interfere with the normal function of immune cells and immune regulatory mechanisms, leading to a decrease in the body's immunity. Experimental research shows that the proliferation of lymphocytes of experimental animals exposed to the compound for a long time will be reduced, and the synthesis of immunoglobulin will be affected, which will weaken the body's resistance to pathogens and easily lead to various infectious diseases.
Early studies in the late 20th century focused on the synthesis and fundamental properties of boronic acids. Researchers explored their reactivity in cross-coupling reactions, particularly the Suzuki-Miyaura coupling, which revolutionized carbon-carbon bond formation. The introduction as a versatile building block facilitated the synthesis of complex aryl derivatives, including pharmaceutical intermediates and functional materials.
In the 2000s, advancements in catalytic systems enhanced the efficiency and selectivity of reactions involving it. Pioneering work in palladium-catalyzed couplings demonstrated its utility in constructing aryl-aryl and aryl-heteroaryl frameworks, crucial for drug discovery. These developments enabled the streamlined synthesis of bioactive molecules, including kinase inhibitors and anti-inflammatory agents.
The 2010s saw expanded applications in materials science, where the compound's boronic acid moiety allowed for dynamic covalent chemistry. Researchers utilized it in the fabrication of stimuli-responsive polymers and metal-organic frameworks (MOFs), leveraging its ability to form reversible bonds under specific conditions.
More recently, studies have highlighted its role in asymmetric synthesis and late-stage functionalization, offering new strategies for accessing enantiomerically pure compounds. Additionally, its compatibility with flow chemistry and continuous processing technologies aligns with modern synthetic demands for sustainability and scalability.
Today, 4-(methoxycarbonyl)phenylboronic acid remains a cornerstone in organic synthesis, with ongoing research exploring its potential in emerging fields such as photoredox catalysis and bioorthogonal chemistry. Its rich history of innovation continues to drive progress in both academic and industrial settings.
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