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5-Methylpyridine-3-boronic acid, also known as 3-(5-methylpyridyl)boronic acid, is an organoboronic acid that belongs to the class of heterocyclic compounds containing a pyridine ring substituted with a methyl group at the 5-position and a boronic acid moiety at the 3-position. This unique molecular structure imparts it with distinct chemical properties and applications in various fields, particularly in organic synthesis and medicinal chemistry.
Chemically, it features a pyridyl ring, which is a six-membered aromatic ring with one nitrogen atom, providing it with aromaticity and stability. The presence of the boronic acid group (-B(OH)₂) makes it a versatile building block for Suzuki-Miyaura cross-coupling reactions, one of the most powerful and widely used methods for forming carbon-carbon bonds in synthetic organic chemistry. This reaction allows for the coupling of aryl or alkenyl halides with boronic acids under mild conditions, thus enabling the synthesis of complex molecules with high efficiency and selectivity.
In medicinal chemistry, it can serve as a key intermediate in the preparation of a range of therapeutically relevant compounds. Due to its pyridyl moiety, which often mimics the binding properties of natural ligands in biological systems, derivatives of this boronic acid may exhibit affinity towards specific receptors or enzymes, opening avenues for the development of novel pharmaceuticals.
In summary, 5-methylpyridine-3-boronic acid stands out as a valuable synthetic tool in organic chemistry, offering a platform for the construction of diverse molecular architectures with potential applications spanning from pharmaceuticals to advanced materials. Its unique combination of structural features and reactivity makes it an indispensable reagent in modern synthetic strategies.
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Chemical Formula |
C6H8BNO2 |
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Exact Mass |
137 |
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Molecular Weight |
137 |
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m/z |
137 (100.0%), 136 (24.8%), 138 (6.5%), 137 (1.6%) |
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Elemental Analysis |
C, 52.62; H, 5.89; B, 7.89; N, 10.23; O, 23.37 |
5-methylpyridine-3-boronic acid, as an organic boron compound, has shown unique application potential in the field of flexible electronic devices. Its unique chemical structure and properties make it an indispensable material in flexible electronic devices. Flexible electronic devices have broad application prospects in wearable devices, portable electronic devices, biomedical implants, and other fields due to their lightweight, bendable, and stretchable characteristics. As an organic material, it plays an important role in the preparation and performance improvement of flexible electronic devices due to its excellent chemical stability, electrical properties, and optical properties.
- Flexible transparent conductive film
Can be used as a dopant or modifier for flexible transparent conductive films. By introducing it into the preparation process of conductive thin films, the conductivity and transparency of the films can be significantly improved. This flexible transparent conductive film has wide application value in fields such as flexible displays, solar cells, touch screens, etc.
- Flexible conductive fibers
It can also be used to prepare flexible conductive fibers. By compounding it with other polymer materials, fiber materials with excellent conductivity can be formed. These conductive fibers have potential application prospects in fields such as smart textiles and wearable devices.
in Flexible Sensors
- Flexible pressure sensor
Plays an important role in flexible pressure sensors. Its unique molecular structure enables the sensor to undergo significant resistance changes when subjected to pressure, thereby achieving accurate measurement of pressure. This flexible pressure sensor has wide application value in wearable devices, biomedical monitoring and other fields.
- Flexible temperature sensor
It can also be used to prepare flexible temperature sensors. By combining it with other thermosensitive materials, sensors with excellent temperature sensitivity can be formed. These temperature sensors have potential application prospects in fields such as biomedical monitoring and environmental monitoring.
- Preparation of electronic skin
Plays an important role in the preparation of electronic skin. Electronic skin is a flexible electronic device that can simulate human skin perception ability, and it has broad application prospects in fields such as human-computer interaction and biomedical monitoring. By introducing it into the preparation process of electronic skin, the sensitivity and stability of electronic skin can be significantly improved.
- Performance improvement of electronic skin
In addition to preparing electronic skins, it can also be used to enhance the performance of electronic skins. For example, by combining it with other functional materials, electronic skin with higher sensitivity, faster response speed, and stronger stability can be formed. These performance improvements enable electronic skins to exhibit better performance in a wider range of application scenarios.
in flexible energy devices
- Flexible solar cells
Plays an important role in flexible solar cells. Its excellent electrical and optical properties enable solar cells to maintain stable performance even under deformation conditions such as bending and stretching. This flexible solar cell has wide application value in wearable devices, portable electronic devices, and other fields.
- Flexible supercapacitor
It can also be used to prepare flexible supercapacitors. Supercapacitors are energy storage devices with high energy density and high power density, which have broad application prospects in flexible electronic devices. By introducing it into the preparation process of supercapacitors, the energy storage performance and stability of capacitors can be significantly improved.
- Flexible electronic tags
Plays an important role in the preparation of flexible electronic tags. Electronic tags are flexible electronic devices that can store and transmit information, and have broad application prospects in logistics, warehousing, and other fields. By introducing it into the preparation process of electronic tags, the information storage capacity and stability of the tags can be significantly improved.
- Flexible electronic circuits
It can also be used to prepare flexible electronic circuits. Flexible electronic circuits are circuit structures that can bend and stretch, and have broad application prospects in wearable devices, portable electronic devices, and other fields. By incorporating the preparation process of electronic circuits, the conductivity and stability of the circuit can be significantly improved.
5-methylpyridine-3-boronic acid has broad application prospects in the field of flexible electronic devices. Its unique chemical structure and properties have made significant progress in the preparation and performance improvement of flexible electronic devices. In the future, with the continuous advancement of science and technology and the increasing demand for the performance of flexible electronic devices, their applications in the field of flexible electronic devices will become more extensive and in-depth.
Firstly
New applications in flexible electronic devices can be further explored. For example, it can be used to prepare new flexible electronic devices such as flexible biosensors and flexible electronic skins to meet people's demand for higher performance and more intelligent flexible electronic devices.
Secondly
It is possible to conduct in-depth research on the composite effects with other materials. By combining it with other functional materials, a new type of composite material with higher performance and more functions can be formed, providing more choices for the preparation and performance improvement of flexible electronic devices.
Finally
Attention can be paid to environmental safety and biocompatibility in flexible electronic devices. By conducting in-depth research on its ecological toxicology and biocompatibility mechanisms, scientific basis and guarantee can be provided for its safe application in related fields.
Mechanism of 5-methylpyridine-3-boronic Acid as an enzyme inhibitor: covalent capture and transition state simulation
Enzyme inhibitors are one of the core directions in modern drug development, which regulate metabolic pathways or signaling processes by blocking enzyme active centers or interfering with substrate binding. In the design of enzyme inhibitors, covalent binding and transition state simulation are two key strategies: the former achieves long-lasting inhibition by forming irreversible covalent bonds, while the latter enhances binding specificity through structural simulation of enzyme catalyzed transition states. 5-Methylpyridine-3-boronic Acid (CAS number 173999-18-3), as a boron containing heterocyclic compound, has shown significant potential in the fields of covalent capture and transition state simulation due to its unique boronic acid group and pyridine ring structure.
Chemical Structure and Reaction Activity of 5-Methylpyridine-3-boronic Acid
Molecular structural characteristics
The molecular formula of 5-Methylpyridine-3-boronic Acid is C ₆ H ₈ BNO ₂, with a molecular weight of 136.94 g/mol. Its structure consists of a pyridine ring, a methyl substituent, and a boronic acid group
Pyridine ring: As an aromatic heterocyclic ring, the nitrogen atom of the pyridine ring endows the molecule with weak alkalinity and can form hydrogen bonds or ionic interactions with acidic amino acids such as glutamic acid and aspartic acid.
Methyl substituent: The methyl group (- CH3) located at the 5th position of the pyridine ring enhances the binding of the molecule to the non-polar region of the enzyme active pocket through hydrophobic interactions, thereby improving selectivity.
Boric acid group: Boric acid (- B (OH) ₂) is the core reactive group, and its empty p-orbitals can form coordination bonds with atoms containing lone pair electrons (such as oxygen, nitrogen, sulfur), or covalently bind with hydroxyl and amino groups.
Reaction activity basis
The reactivity of boronic acid groups originates from their Lewis acidity:
Reaction with diols/polyols: Boric acid can form pentagonal or hexagonal cyclic esters with neighboring diols (such as sugars, nucleotides) or cis diols (such as vitamin C). This reaction is reversible at physiological pH and is commonly used for sugar sensing or drug delivery.
Reaction with amino groups: Under alkaline conditions, boric acid can form covalent bonds with primary or secondary amines, and the irreversibility of this reaction increases with pH, which is the key to designing covalent inhibitors.
Reaction with thiols: Although boronic acid has lower reactivity with thiol groups of cysteine, its covalent capture ability can be enhanced through structural modifications such as introducing electron withdrawing groups.
Covalent capture mechanism: targeting specific amino acid residues
Covalent inhibitors achieve long-lasting inhibition by forming covalent bonds with specific amino acid residues of the target protein. The covalent capture mechanism of 5-Methylpyridine-3-boronic Acid mainly involves the following steps:
Target recognition and reversible binding
Non covalent interactions: In the initial stage, inhibitors bind to non covalent sites of enzyme activity pockets through hydrophobic interactions of pyridine rings, hydrogen bonding of boronic acid, or ionic interactions. For example, in the design of serine hydrolases, the pyridine ring can be embedded in a hydrophobic sub pocket, while the boronic acid group is located near the serine hydroxyl group in the catalytic triad (Ser His Asp).
Induced binding effect: The initial binding of enzymes and inhibitors may induce conformational changes in the active pocket, bringing target residues (such as serine and cysteine) closer to boronic acid groups, creating conditions for covalent reactions.
Covalent bond formation
Reaction with serine: Under alkaline conditions (such as pH 7.5-9.0), the hydroxyl oxygen atom of serine attacks the empty p orbital of the boronic acid group, forming a tetrahedral transition state, followed by dehydration to form covalent ester bonds. This reaction has high irreversibility and can inhibit enzyme activity for a long time.
Reaction with cysteine: Although natural boric acid has low reactivity with cysteine, introducing electron withdrawing groups (such as fluorine and nitro) or optimizing pyridine ring substituents can enhance the electronegativity of boric acid and promote the formation of thiol boronic acid covalent bonds. For example, the inhibitory activity of 5-fluoro-3-pyridylboronic acid on cysteine protease is significantly higher than that of unmodified analogues.
Reaction with tyrosine: The phenolic hydroxyl group of tyrosine can also form covalent bonds with boric acid, but the reaction rate is slow and requires a specific enzyme environment (such as high pH or metal ion catalysis) to accelerate the reaction.
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