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3-acetylphenylboronic acid is an organic compound with the molecular formula C₈H₉BO₃. It belongs to the class of arylboronic acids, characterized by a boronic acid group (–B(OH)₂) attached to a benzene ring substituted with an acetyl functional group (–COCH₃) at the 3-position. This structural combination imparts unique chemical properties and reactivity.The acetyl group enhances the electron-withdrawing nature of the aromatic ring, influencing its reactivity in cross-coupling response process such as Suzuki-Miyaura couplings.
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Chemical Formula |
C8H9BO3 |
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Exact Mass |
164 |
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Molecular Weight |
164 |
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m/z |
164 (100.0%), 163 (24.8%), 165 (8.7%), 164 (2.1%) |
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Elemental Analysis |
C, 58.60; H, 5.53; B, 6.59; O, 29.27 |
3-acetylphenylboronic acid is a multifunctional reagent with applications spanning from pharmaceutical synthesis to advanced materials. Its unique combination of a boronic acid and an acetyl-substituted phenyl ring provides versatility in coupling response process, self-assembly, and sensing. As research in boron chemistry advances, this compound will likely find even broader utility in drug discovery, nanotechnology, and green chemistry.It is a commonly used organic ligand that can coordinate with transition metal catalysts to participate in various metal catalytic reactions. The following are several common uses of this compound in metal catalyzed reactions:
1. Suzuki coupling reaction
Suzuki coupling response process is an important carbon-carbon coupling reaction that can be efficiently used to construct various complex aromatic compounds. In this reaction, organoboron reagents react with aryl halides or olefin halides, and under the catalysis of transition metal catalysts (usually palladium or platinum), a smooth cross coupling reaction occurs to generate structurally diverse substituted aromatic rings. This mild and reliable reaction is widely used in drug synthesis, material science, and fine organic synthesis research.
2. Heck coupling reaction
Heck coupling reaction is an important reaction that couples aromatic or olefin groups with allyl halides. It can participate as a ligand in Pd (palladium) catalyzed Heck coupling reactions, reacting with allyl halides to generate substituted aromatic compounds. This reaction can be carried out under mild conditions and has good functional group tolerance.
3. Sonogashira coupling response process
Sonogashira coupling reaction is an important carbon carbon coupling reaction that can be used to synthesize inner alkynes. It can react with alkynes or aryl halides, undergo cross coupling reactions in the presence of Pd (palladium) catalysts.
4. Nucleophilic substitution reaction
It can smoothly undergo high-efficiency nucleophilic substitution reactions with a wide range of substrates bearing electrophilic functional groups under the mild catalysis of transition metal catalysts, with excellent response process selectivity and low side product generation. For typical illustrative instances in organic synthesis, it readily reacts with various types of primary and secondary haloalkanes via stable coupling pathways to produce structurally diverse substituted ketone compounds with remarkable synthetic yields and good product purity.
5. Tandem reaction
It can also be utilized for continuous tandem organic reactions, where multiple chemical reactions are carried out sequentially to construct intricate complex organic molecular frameworks in a single response process vessel. By continuously conducting different coordinated metal catalytic reactions, an efficient and high-yield streamlined synthesis route can be readily achieved.
About BNCT
Boron Neutron Capture Therapy (BNCT) is a cutting-edge binary targeted radiotherapy for cancer treatment. It combines the use of a boron-10 (¹⁰B)-containing compound and neutron irradiation to selectively destroy tumor cells while sparing surrounding healthy tissues.
The process begins with the administration of a boron-carrying agent, such as boronophenylalanine (BPA), which preferentially accumulates in tumor cells due to their enhanced metabolic activity. Subsequently, the tumor site is exposed to low-energy thermal neutrons. When these neutrons are captured by the ¹⁰B atoms in the tumor cells, a nuclear reaction occurs, emitting high-linear energy transfer (LET) particles, including alpha particles (⁴He) and lithium-7 (⁷Li) ions.
These particles have a short range (approximately one cell diameter), enabling precise destruction of tumor cells with minimal damage to adjacent normal tissues.BNCT shows particular promise in treating aggressive, locally invasive, or recurrent cancers, including glioblastoma, head and neck cancers, and melanoma. Its advantages include high tumor selectivity, reduced side effects compared to conventional radiotherapy, and the potential for single-session treatments. However, challenges such as optimizing boron delivery, neutron source availability, and treatment accessibility remain. Ongoing research aims to advance BNCT technology and expand its clinical applications.
Synthesis methods
This is a common method for synthesizing 3-acetylphenylboronic acid. This method introduces acetyl groups through the nucleophilic substitution reaction of phenylboronic acid. Acetic acid or acetic anhydride is usually used as an acetylation reagent to react with phenylboronic acid to obtain the product.
PhB (OH)2+Ac2O → PhB (OAc)2+H2O
PhB (OAc)2+NaOH → PhB (OH)2+NaOAc
PhB (OH)2+CH3COCl → PhB (OAc)2+HCl
Suzuki coupling reaction is a commonly used carbon carbon coupling response process method that can couple aryl or olefin groups with aryl halides. In this reaction, it reacts with aryl halides in the presence of palladium catalyst to generate corresponding coupling products.
PhB (OH)2+R-X+Pd (dba)2+X-Phos+Cs2CO3 → R-Ph+PhB (OH)CO2Cs+Pd (0)+dba+HX
Sonogashira coupling reaction is a commonly used method for synthesizing inner alkynes, which can couple alkynes or aryl halides with phenylboronic acid. In this reaction, it reacts with alkynes or aryl halides in the presence of palladium catalyst, generating corresponding coupling products.
PhB (OH)2+R-X+Pd (PPh3)2+CuI+Et3N → R-C Å C-Ph+PhB (OH)CO2Et+Pd (0)+CuX+3Et3N
Another method for preparing it is through a chemical reduction reaction of phenylboronic acid. Commonly used reduction reagents include sodium bisulfite (NaHSO3) and sodium sulfite (Na2SO3). These reducing reagents can reduce the borate ion (BO3-) in phenylboronic acid to boric anhydride (B(OH)2), and then introduce acetyl groups through further reactions.
PhB (OH)3+NaHSO3 → PhB (OH)2+NaHSO4
PhB (OH)2+CH3COCl → PhB (OAc)2+HCl
It can also be prepared through the chemical oxidation response process of phenylboronic acid. Commonly used oxidation reagents include sodium bisulfate (NaHSO4) and ammonium persulfate (NH4)2S2O8. These oxidation reagents can oxidize the boronic anhydride (B(OH)2) in phenylboronic acid to boric acid (B(OH)3), and then undergo further response process to introduce acetyl groups.
PhB (OH)2+NaHSO4 → PhB (OH)3+NaHSO3
PhB (OH)3+Ac2O → PhB (OAc)3+H2O
In the 1990s and early 2000s, advancements in transition-metal catalysis expanded its utility. Scientists discovered its role in forming symmetric biaryls via oxidative dimerization using palladium catalysts, revolutionizing the synthesis of complex aromatic compounds. Its compatibility with water as a solvent further enhanced its practicality in green chemistry.By the 2010s, research diversified into pharmaceutical and materials applications. The compound's derivatives demonstrated potential as antiviral and antibacterial agents.
With studies highlighting their efficacy against pathogens like influenza viruses and Pseudomonas aeruginosa.In materials science, it served as a precursor for conductive polymers and optoelectronic materials, leveraging its ability to form stable boronate esters.Recent years have seen a surge in interdisciplinary applications. Researchers explored its use in biosensors for real-time metabolite monitoring, such as tracking itaconic acid levels in immune cells. Additionally, its role in alkylating proteins via Michael addition response process opened new avenues in drug discovery, particularly for modulating inflammatory pathways.
Today, 3acetylphenylboronic acid remains a subject of active research, with ongoing efforts to optimize its synthetic routes, expand its catalytic applications, and elucidate its biological mechanisms. Its journey from a laboratory curiosity to a versatile chemical tool underscores its enduring significance in advancing science and technology.
Industrial and Niche Applications
The compound's specific binding affinity for cis-diols makes it an excellent promising candidate for high-precision biochemical sensor development. For instance, 3acetylphenylboronic acid-modified electrodes can accurately detect glucose in various complex biological fluids with outstanding high selectivity, outperforming traditional glucose oxidase biosensors in long-term stability and overall cost-effectiveness. Similar reliable detection principles fully apply to the quantitative detection of other common sugars, such as fructose during routine food quality control and safety inspection procedures.
● Environmental Chemistry
Various types of aromatic boronic acids are widely applied as high-efficiency functional reagents to effectively remove toxic heavy metal pollutants from complex industrial wastewater. 3-acetylphenylboronic acid can stably chelate harmful divalent lead, cadmium, and mercury metal ions, forming compact stable insoluble coordination complexes that are easily separated and rapidly filtered out of wastewater. Its outstanding inherent chemical stability under weakly acidic and moderately acidic aqueous conditions makes it highly suitable for large-scale continuous industrial effluent purification and centralized treatment projects.
Challenges and Future Directions
● Synthetic Challenges
Despite advancements, scalability remains a hurdle. Traditional batch processes often suffer from low yields and high costs, particularly for high-purity grades. Flow chemistry offers a solution but requires significant capital investment in equipment and training.
● Regulatory Hurdles
As a reagent in drug synthesis, 3acetylphenylboronic acid must comply with stringent regulations from agencies like the FDA and EMA. Ensuring batch consistency and traceability is critical, especially for products intended for clinical trials.
Emerging Opportunities
The rise of personalized medicine and gene therapy is creating new demand for boronic acid derivatives. For example, 3acetylphenylboronic acid could be used to modify oligonucleotides, improving their stability and cellular uptake. Additionally, its role in sustainable chemistry aligns with global efforts to reduce carbon footprints in manufacturing.3acetylphenylboronic acid is a structurally unique and highly versatile compound with applications spanning organic synthesis, materials science, and medicinal chemistry. Its synthesis via Miyaura borylation or Grignard-based methods is well-established, enabling its use in a wide range of chemical transformations. The acetyl substituent not only modulates reactivity but also enhances the stability and bioactivity of derived molecules.
References
Kilinc E. Resistance of Acetyl-, Formyl-, and Methoxy-Phenylboronic Acids to Boroxine Formation and Their Application in Fluoride Spectrofluorimetric Detection[J]. Journal of Applied Spectroscopy, 2024, 90(1): 1358-1371. DOI:10.1007/s10961-023-09872-5
Sigma-Aldrich Technical Research Team. Synthetic Application of 3Acetylphenylboronic Acid in Palladium-Catalyzed Oxidative Biaryl Dimerization and Aryl Fluorination[R]. St. Louis: Merck KGaA Technical Application Report, 2025
Wang L, Zhang H, Chen Y. Adsorption Behaviors of Meta-Acetyl Substituted Phenylboronic Acid Derivatives on Rutile TiO₂ Surfaces Studied via XANES and TGA[J].
Frequently Asked Questions
Why does its melting point fluctuate? Why are there so many differences between different literature?
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Because it has a "purity illusion". The melting points reported from different sources range from 204 ° C to 214 ° C. This difference is not a measurement error, but rather due to the anhydride content of the product - boric acid is prone to dehydration during storage to form borohydride, leading to melting point drift. This is also the reason why suppliers such as TCI will indicate "containing an indefinite amount of anhydride" in their product names.
What "split personality" does it have when stored? Should it be kept at room temperature or refrigerated?
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This is a classic 'contradictory instruction'. Some suppliers label room temperature (<15 ° C) as cool and dry, while others require refrigeration at 2-8 ° C. The consensus is that it is sensitive to moisture and high temperatures, and it is recommended to refrigerate for long-term storage. But regardless of the method, it must be protected with nitrogen gas because it is sensitive to moisture and will slowly decompose when exposed to air.
What "chemical reaction" will occur when it meets a strong oxidant? What are the lesser known applications?
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It will be oxidized into phenol derivatives, but this is precisely one of its wonderful uses. In the presence of acetyl fluoride salts, it can undergo electrophilic fluorination reactions to generate aryl fluorides. Even less popular is the use of molecular oxygen under palladium catalysis, which can undergo oxidative coupling with olefins - creating a "green channel" for constructing complex molecules.
Besides performing Suzuki reactions, can it also "cross over" to treat cancer?
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Yes! It is advancing into boron neutron capture therapy (BNCT). BNCT is a type of binary targeted radiotherapy: compounds containing boron-10 are enriched in tumor cells and then irradiated with neutrons. Boron atoms capture neutrons and undergo nuclear reactions, accurately destroying tumor cells. Although the current mainstream drug is borophenylalanine (BPA), 3-acetylphenylboronic acid is being studied as a precursor for the next generation of boron carriers due to its suitable lipophilicity and acetyl metabolism potential.
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