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2-Chloro-4-pyridylboronic acid, also known as 2-chloropyridine-4-boronic acid, is an organoboronic acid compound that belongs to the class of heterocyclic boronic acids. It is characterized by the presence of a pyridine ring, a six-membered aromatic heterocycle containing a nitrogen atom, substituted with a chloro group at the 2-position and a boronic acid moiety attached to the 4-position.This unique structure imparts valuable chemical reactivity to the product, making it a versatile building block in organic synthesis.
The boronic acid functionality is particularly reactive towards a wide range of electrophiles, enabling it to participate in cross-coupling reactions such as Suzuki-Miyaura coupling, a powerful tool for carbon-carbon bond formation.In medicinal chemistry and drug discovery, it can serve as a precursor for the synthesis of bioactive molecules with pyridyl scaffolds, which are frequently encountered in pharmaceuticals due to their ability to modulate a diverse array of biological processes.
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Chemical Formula |
C5H5BClNO2 |
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Exact Mass |
157.01 |
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Molecular Weight |
157.36 |
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m/z |
157.01 (100.0%), 159.01 (32.0%), 156.01 (24.8%), 158.01 (7.9%), 158.01 (5.4%), 160.01 (1.7%), 157.02 (1.3%) |
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Elemental Analysis |
C, 38.16; H, 3.20; B, 6.87; Cl, 22.53; N, 8.90; O, 20.33 |
Key intermediates in organic synthesis
The core value of 2-chloro-4-pyridylboronic acid lies in the synergistic effect between its boronic acid group (- B (OH) ₂) and the 2-position chlorine atom of the pyridine ring. In the Suzuki Miyaura coupling reaction, the product can react with aryl or vinyl halides to efficiently construct carbon carbon bonds.
For example:Drug molecular synthesis: By coupling with bromoaromatic hydrocarbons, a pyridine aryl skeleton can be rapidly constructed, which is widely present in anti-tumor drugs (such as imatinib analogs) and antiviral drugs (such as lopinavir intermediates).
Materials Science Applications: In the field of organic optoelectronic materials, their coupling products can be used to prepare conjugated polymers, improving the light absorption efficiency and charge transfer performance of materials.
As a substrate for peroxide mediated hydroxyl deprotonation reaction, 2-chloro-4-pyridinboronic acid can selectively generate halogenated hydroxypyridine derivatives. For example:
Reaction conditions: In the presence of tert butanol peroxide (TBHP), the chemical can be converted to 2-chloro-4-hydroxypyridine with a yield of up to 85%.
Application scenario: This type of hydroxypyridine is a key intermediate for the synthesis of antibiotics (such as pyridine amides) and antifungal drugs (such as terbinafine analogues).
The boronic acid group can form reversible boronic ester bonds with neighboring diols, which makes it uniquely applicable in self-healing materials and stimulus responsive polymers
Self repairing material: Introducing it into the polymer backbone, achieving autonomous repair of material damage through dynamic breaking and recombination of boronic ester bonds.
Drug controlled release system: Utilizing the pH sensitivity of boronic ester bonds, design nanocarriers that can specifically release drugs in the tumor microenvironment (weakly acidic).
Multi functional modules in drug development
The pyridine ring is a common pharmacophore of kinase inhibitors, and it can participate in drug design through the following ways:
Structural modification: Introducing a boronic acid group at the 4-position of the pyridine ring can enhance hydrogen bonding interactions with the kinase ATP binding pocket and improve inhibitory activity.
For example, derivatives based on this chemical exhibit a 3-fold increase in inhibitory activity against EGFR kinase compared to traditional inhibitors.
Targeted delivery: Boric acid groups can specifically bind to the cis diol structure on glycoproteins (such as transferrin) to achieve targeted delivery of drugs to tumor cells.
This chemical exhibits multiple potentials in the development of anti-tumor drugs:DNA embedding agent: interferes with DNA replication process through π - π stacking of pyridine ring and DNA base. The experiment showed that its platinum complex had an IC ₀ value of 2.3 μ M for breast cancer cells.
Topoisomerase inhibitor: Boric acid groups can stabilize topoisomerase DNA complexes and block DNA unwinding. Related derivatives show significant anti-tumor activity in colon cancer models.
2-chloro-4-pyridylboronic acid and its derivatives have potential applications in antibacterial and antiviral fields:
Antibacterial mechanism: exerting bactericidal effect by disrupting the integrity of bacterial cell membrane or inhibiting DNA gyrase activity. The minimum inhibitory concentration (MIC) for Staphylococcus aureus is 8 μ g/mL.
Antiviral activity: Inhibition experiments against HIV-1 reverse transcriptase showed that the IC ₅₀ value of its boronic ester derivative was 0.5 μ M, which was superior to the clinical drug nevirapine.
Functional components in materials science
This compound has important applications in organic light-emitting diodes (OLEDs) and organic solar cells (OSCs):OLED material: As an electron transport layer material, the nitrogen atom of its pyridine ring can effectively lower the LUMO energy level and enhance electron mobility. The external quantum efficiency (EQE) of the device based on this chemical reaches 15.2%.
OSC material: By blending with fullerene derivatives, a nanoscale phase separation structure is formed, which improves the energy conversion efficiency of the device to 9.8%.
It can be used as a ligand to construct functionalized MOF materials:
Gas adsorption: MOF-502, formed by coordination with zinc ions, has an adsorption capacity of 3.2 mmol/g (273 K, 1 bar) for CO ₂ and can be used for industrial waste gas treatment.
This chemical can achieve dynamic surface modification of materials through boronic ester bonds:
Biosensor: After modifying it on the surface of a gold electrode, it can specifically bind to glucose oxidase to construct a high-sensitivity glucose sensor (with a detection limit as low as 0.1 μ M).
Anti fouling coating: Introducing this chemical into polymer coatings and achieving self-healing through dynamic exchange of boronic ester bonds, significantly reducing the adhesion rate of marine organisms.
Detection tools in analytical chemistry
Design of fluorescent probes
By utilizing boronic acid groups for specific recognition of carbohydrate molecules, highly selective fluorescent probes can be designed
Glucose detection: The probe based on this chemical has a detection limit of 0.5 μ M for glucose under physiological pH conditions and is not affected by fructose interference.
Cell imaging: By labeling cell surface glycoproteins, specific imaging of tumor cells is achieved, with a 10 fold increase in signal-to-noise ratio (S/N) compared to traditional methods.
Modifiers for chromatographic stationary phases
It can be used as a modifier to improve chromatographic separation performance:
Chiral separation: After covalently bonding it to the surface of silica gel, the separation factor (α) for chiral drugs such as ibuprofen reaches 1.8, which is 40% higher than that of unmodified columns.
Hydrophilic interaction chromatography (HILIC): The modified stationary phase exhibits excellent performance in the separation of polarchemicals, with a recovery rate of 98% for nucleosides.
Potential applications in the field of agriculture
Research and development of new herbicides
Based on the pyridine boronic acid structure of this chemical, low toxicity and high efficiency herbicides can be designed:Mechanism of action: By inhibiting the activity of acetolactate synthase (ALS) in weeds, the synthesis of branched chain amino acids is blocked. Experiments have shown that its inhibitory activity against barnyard grass is twice that of traditional herbicides.Environmental friendliness: The half-life in soil is only 3 days, significantly lower than commercial herbicides (usually>30 days), reducing the risk of environmental pollution.
Plant growth regulators
2-chloro-4-pyridylboronic acid and its derivatives can regulate plant hormone signaling pathways:
Promoting growth: At a concentration of 0.1 μ M, the tiller number and grain yield of rice can be significantly increased (by 15%).
Enhanced stress resistance: By inducing the activity of antioxidant enzymes (SOD, POD), crops can improve their tolerance to drought and salt stress.
I. Overview of Synthetic Routes
2-Chloro-4-pyridineboronic acid is an important organoboron intermediate widely applied in Suzuki coupling reactions. The dominant laboratory synthesis route adopts the low-temperature halogen-metal exchange boration method.
Using 2-chloro-4-bromopyridine as the starting material, the target product is prepared via three steps: low-temperature lithiation with n-butyllithium, addition of borate ester and acidic hydrolysis.
This route features high reaction selectivity and effectively prevents dehalogenation side reactions of the chlorine atom at the 2-position. The overall yield is stably maintained at 65%–75%. With simple operation, it is suitable for small and medium-scale preparation.
II. Low-Temperature Lithiation Reaction
The reaction must be carried out under strict anhydrous and oxygen-free conditions to prevent water and oxygen from decomposing active intermediates.
Dissolve the raw material 2-chloro-4-bromopyridine in anhydrous tetrahydrofuran (THF), and cool the solution to -78 °C in a dry ice-acetone bath. Slowly add n-butyllithium solution in n-hexane dropwise while keeping the temperature below -70 °C throughout the process.
After dropping, stir the mixture at constant temperature for 40 minutes to complete bromine-lithium exchange and generate highly active 2-chloro-4-lithiopyridine intermediate. Low temperature ensures exclusive reaction at the target site and avoids damage to the pyridine ring as well as by-product formation.
III. Boration Addition and Acidic Hydrolysis
Keep the system at low temperature, then slowly add triisopropyl borate as the boron source and react at constant temperature for 1.5 hours. Gradually raise the temperature to 0 °C and continue the reaction for another 1 hour to finish nucleophilic addition and form stable borate ester intermediate.
Upon completion of the reaction, quench the system with dilute hydrochloric acid and adjust the pH value to 1–2. Stir the mixture at room temperature for 2 hours to fully hydrolyze the borate ester into crude 2-chloro-4-pyridineboronic acid. Mild hydrolysis conditions can maximally retain the chloro substituent in the molecule.
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IV. Product Separation and Purification
Extract the hydrolyzed mixture repeatedly with ethyl acetate, and combine all organic phases. The combined organic layer is washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to remove the solvent and obtain the crude product.
The crude product is recrystallized using ethyl acetate-petroleum ether mixed solvent, and vacuum-dried to afford the final pure white solid. HPLC analysis shows the product purity exceeds 98%. Its chemical structure is further confirmed by NMR and LC-MS, which meets the quality requirements for organic synthesis intermediates.
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What is 2 Chloropyridin 4 yl boronic acid?
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2-Chloropyridine-4-boronic acid is a nicotinic acetylcholine receptor antagonist that has been shown to be effective against trypanosomiasis. It blocks the binding of acetylcholine to its receptor, which prevents the propagation of an action potential in the postsynaptic cell.
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