3-Cyanophenylboronic acid is an important multifunctional organic synthetic building block that possesses both a boronic acid group (-B(OH)₂) and a cyano group (-CN) attached to a benzene ring at the meta-position relative to each other. This specific substitution pattern defines its unique chemical reactivity: the boronic acid group allows it to participate efficiently in Suzuki-Miyaura cross-coupling reactions, a cornerstone method in modern organic synthesis for constructing carbon-carbon bonds, enabling the facile introduction of the 3-cyanophenyl moiety into more complex molecular architectures. Simultaneously, the strongly electron-withdrawing cyano group profoundly influences the electronic properties of the aromatic ring, moderating the reactivity of the boronic acid and enhancing the stability of the molecule. Furthermore, the cyano group itself is a highly versatile functional handle; it can be hydrolyzed to a carboxylic acid, reduced to an aminomethyl group, or serve as a hydrogen bond acceptor in molecular recognition. Owing to this valuable combination of features, 3-cyanophenylboronic acid is extensively utilized in the pharmaceutical industry for the synthesis of active pharmaceutical ingredients (APIs), in materials science for the creation of organic electronic materials and metal-organic frameworks (MOFs), and as a crucial reagent in chemical biology and sensor development.
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Chemical Formula |
C14H24S |
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Exact Mass |
224 |
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Molecular Weight |
224 |
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m/z |
224 (100.0%), 225 (15.1%), 226 (4.5%), 226 (1.1%) |
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Elemental Analysis |
C, 74.93; H, 10.78; S, 14.29 |
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3-cyanophenylboronic acid is an important organic compound, and its unique chemical properties are attributed to the cyanide and boronic cid groups in its structure. The presence of a cyanide group gives the compound high reactivity, while the boronic cid group endows it with good water solubility. This dual nature enables it to play a unique role in chemical reactions.
As a signal transmission medium
It can also serve as a signal transmission medium, playing a role in transmitting signals in chemical sensors. By reacting with the target substance, its chemical properties or physical state can be changed, thereby triggering the signal transduction mechanism of the sensor.
Specific examples:
Fluorescence sensor:
By utilizing its interaction with certain fluorescent substances, a fluorescence sensor can be prepared. When the target substance reacts with it, it changes the luminescent properties of the fluorescent substance, thereby achieving detection of the target substance. This fluorescent sensor can be applied in fields such as biomolecule detection and environmental monitoring.
Electrochemical sensor:
By fixing it on the electrode surface, an electrochemical sensor can be prepared. When the target substance reacts with it, it changes the charge state or current magnitude on the electrode surface, thereby achieving detection of the target substance. This electrochemical sensor can be applied in fields such as water quality monitoring and food safety.
Specific application cases in the field of chemical sensors
Case 1: Preparation and Application of Hydrogen Peroxide Sensor
Preparation process:
Fix 3-cyanophenylboronic cid or its derivatives on the electrode surface to form a sensing film.
By optimizing the preparation conditions of the sensing membrane, such as concentration, temperature, time, etc., the performance of the sensor can be improved.
Connect the prepared sensor to an electrochemical workstation for performance testing.
Application example:
Environmental monitoring: Use hydrogen peroxide sensors to monitor the concentration of hydrogen peroxide in the atmosphere and evaluate air quality.
Food processing: In the process of food processing, hydrogen peroxide sensors are used to monitor the residual amount of hydrogen peroxide to ensure food safety.
Case 2: Preparation and Application of Glucose Sensor
Preparation process:
Combine itself or its derivatives with fluorescent substances to form fluorescent sensing materials.
Fix fluorescent sensing materials on a carrier, such as glass or plastic sheets, to form a sensor.
By optimizing the preparation conditions of fluorescent sensing materials and the structure of the sensor, the performance of the sensor can be improved.
Application example:
Medical diagnosis: glucose sensor is used to monitor the glucose concentration in diabetes patients, providing an important basis for treatment.
Sports Health: During exercise, glucose sensors are used to monitor athletes' blood sugar levels, evaluate exercise effectiveness and health status.
Case 3: Preparation and Application of Enzyme Sensors
Preparation process:
Combine it with enzymes to form enzyme sensing materials.
Fix the enzyme sensing material on the electrode surface to form an enzyme sensor.
By optimizing the preparation conditions of enzyme sensing materials and the structure of the sensor, the performance of the sensor can be improved.
Application example:
Biomolecular detection: using enzyme sensors to detect specific molecules in biological samples, such as proteins, nucleic cids, etc.
Environmental pollution monitoring: using enzyme sensors to monitor the concentration of pollutants in the environment, such as heavy metal ions, organic pollutants, etc.
Application in detection and measurement
Application in glucose detection
3-cyanophenylboronic acid can also be used as a probe for specific detection of trace amounts of glucose in urine.
Specific examples:
Glucose detection probe: Add 3-cyanophenylboronic cid pinal ester to the reaction flask and dilute HCl for hydrolysis. Through a series of chemical reactions and extraction processes, 3-cyanophenylboronic cid can ultimately be obtained. The specific reaction between 3-cyanophenylboronic cid and glucose can be used to detect trace amounts of glucose in urine. This method has the advantages of high sensitivity and specificity, which provides strong support for the diagnosis of diabetes and other diseases.
Application in environmental monitoring
3-cyanophenylboronic cid can also be used for detection and measurement in environmental monitoring. For example, it can be applied to water quality monitoring to assess water quality by detecting the content of specific pollutants in the water.
Specific examples:
Water quality monitoring: By utilizing the specific reaction between 3-cyanophenylboronic cid and target pollutants, the determination of pollutant content in water can be achieved. This method has the advantages of easy operation and high sensitivity, providing a powerful tool for water quality monitoring. Meanwhile, 3-cyanophenylboronic cid can also be used in atmospheric environmental monitoring to evaluate air quality by detecting the content of specific pollutants in the atmosphere.
Application in food safety testing
In the field of food safety testing, 3-cyanophenylboronic cid also has a wide range of applications. For example, it can be applied to the detection of harmful substances such as additives and pesticide residues in food.
Specific examples:
Food additive detection: By utilizing the specific reaction between 3-cyanophenylboronic cid and target food additives, the content of additives in food can be determined. This method has the advantages of high accuracy and good reproducibility, providing strong support for food safety testing.
Pesticide residue detection: reacting 3-cyanophenylboronic cid with pesticide residues containing specific functional groups, and accurately determining the residual amount of pesticides in food by detecting the generation of reaction products. This method provides a new idea and approach for pesticide residue detection.
Due to the presence of active cyanide groups in 3-cyanobenzene, neither the organic lithium reagent method nor the Grignard reagent method can be used to prepare 3-cyanobenzoic acid. Miyaura boronation reaction is a type of reaction in which aryl or alkenyl halides or trifluorosulfonic cid ester derivatives undergo coupling reactions with diboronic cid pinacol esters in the presence of palladium catalysts to prepare corresponding boric cid pinacol esters. This reaction has the characteristics of mild conditions, no need for low-temperature oxygen and water separation, and good functional group tolerance, which to some extent compensates for the shortcomings of using highly active Grignard reagents and lithium reagents to prepare such compounds. Allowing reactants to contain groups such as cyano, nitro, amino, hydroxyl, ester, or carbonyl groups, arylborate esters can be prepared in one step from substituted aryl halides. This article uses 3-cyanobromobenzene as the raw material, with pinacol diboronate (B2Pin2) as the boronizing agent, to prepare 3-cyanobenzoic cid under mild reaction conditions through Miyaura boronization reaction. The effects of different catalysts and bases on the product yield were studied, and the resulting product was analyzed and characterized.
Synthesis of 3-Cyanophenylboronic Acid
Method 1:
Compound 3 (2.00g, 8.73mmol) and NaIO 4 (5.60g, 26.19mmol) were added to a mixed solution of tetrahydrofuran (40mL) and water (10mL), and reacted at room temperature for 30 minutes. 1mol/L of HCl aqueous solution (6.10mL) was added, and the reaction continued for 2.5 hours. Most of the tetrahydrofuran and ethyl acetate (10mL) were evaporated under reduced pressure × 3) Extract, merge organic phases and wash with saturated sodium chloride solution, dry with anhydrous sodium sulfate, evaporate under reduced pressure to obtain solvent. The crude product is separated and purified by column chromatography, and 0.96g of the product is obtained using petroleum ether/ethyl acetate (5:1, v/v) as eluent, with a yield of 75.00%. It is a white solid.
Method 2:
Add 3 cyanophenylboronic cid pinacol ester to the reaction flask and add dilute HCl dropwise for hydrolysis. The solution first generates precipitation, and as the precipitation gradually disappears, adjust the pH value of the system to 1. Add a 25% mass fraction of NaOH solution dropwise to the solution until the pH value is 13, and stir for 1 hour. Separate the liquid, extract the organic phase with 15 mL of 10% NaOH by mass, merge the aqueous phase, and extract the alkaline solution twice with 15 mL of THF. Adjust the pH value of the obtained alkaline solution with dilute HCl, and turbidity will begin to form. Gradually, flocculent substances will appear, and the pH value will be adjusted to 5.0. Extract the aqueous phase with 70 mLTHF, spin dry the organic phase, and purify to obtain 3 cyanophenylboronic cid.
3-Cyanophenylboronic Acid (3-Cyanophenylboronic Acid) is an organic compound with unique chemical properties. The following provides a detailed introduction from four aspects: structural characteristics, reactivity, physical properties, and stability and storage conditions:
Structural characteristics
The molecular structure of 3-Cyanophenylboronic Acid contains a benzene ring. At the meta position of the benzene ring, there is a cyanide group (-CN) and a boronic acid group (-B(OH)₂) connected respectively. The cyanide group acts as a strong electron-withdrawing group, which can enhance the electron deficiency of the benzene ring and increase the reactivity of the compound. The boronic acid group gives it good water solubility and enables it to participate in various organic reactions, especially forming stable coordination bonds or covalent bonds with compounds containing hydroxyl or amino groups.
Reactivity
Suzuki-Miyaura coupling reaction: 3-Cyanophenylboronic Acid can efficiently participate in this reaction, which is an important method for forming carbon-carbon bonds. Through this reaction, various organic compounds with complex structures, such as drug molecules, pesticides, and key intermediates in materials science, can be synthesized.
Forming stable complexes with diols: 3-Cyanophenylboronic Acid can form stable complexes with diol compounds. This property is particularly useful in organic synthesis and can be used to protect diol groups or as part of a synthesis strategy.
Further conversion of the cyano group: The cyano group itself is also a highly reactive functional group and can be further converted into other functional groups, such as carboxylic acids, amines, or ketones. For example, the cyano group can be converted into a carboxylic acid through a hydrolysis reaction, into an amine through a reduction reaction, or form a ketone with a Grignard reagent.
Physical properties
Cyanophenylboronic Acid is usually a white to pale yellow solid at room temperature. It has a relatively high melting point, ranging from approximately 298°C to 300°C, indicating excellent thermal stability. It is soluble in organic solvents such as methanol, which facilitates its application in organic synthesis.
Stability and Storage Conditions
Stability: 3-Cyanophenylboronic Acid is stable under normal temperature and pressure. However, it should be avoided from contact with strong oxidants as they may trigger oxidation reactions, causing the compound to decompose or deteriorate.
Storage Conditions: To maintain its stability, 3-Cyanophenylboronic Acid should be stored in a sealed container and kept in a cool, dry place. For long-term storage, it is recommended to maintain a low temperature (such as 4°C or -20°C) to reduce the risks of thermal motion and oxidation reactions.
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