4-Dibenzothiopheneboronic acid is an organic compound with the chemical formula C12H9BO2S, CAS 108847-20-7. It is a white or almost white solid with a certain pungent odor. The molecular structure contains a boric acid group and a diphenyl sulfur group. It does not exhibit spontaneous combustion and is stable at room temperature, but may undergo decomposition or oxidation reactions at high temperatures or when exposed to air. It is acidic and can react with alkali to form salts. It can be used to synthesize dyes and pigments, such as azo dyes, phthalocyanine dyes, and fluorescent dyes.
These dyes and pigments have bright colors and excellent fastness, and can be used for dyeing and printing materials such as textiles, leather, paper, etc. It has broad application potential in the agricultural field, playing an important role in providing better protection for crops, promoting their growth and development, improving their stress resistance, improving soil environment, controlling agricultural residues, and improving the efficiency and quality of agricultural product processing.
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C.F |
C12H9BO2S |
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E.M |
228 |
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M.W |
228 |
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m/z |
228 (100.0%), 227 (24.8%), 229 (13.0%), 230 (4.5%), 228 (3.2%), 229 (1.1%) |
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E.A |
C, 63.20; H, 3.98; B, 4.74; O, 14.03; S, 14.06 |
Environmental pollutant detection and analysis
As an organic boron compound, its unique chemical structure may play an important role in environmental pollutant detection. In today's increasingly severe environmental pollution, accurate and rapid detection and analysis of pollutants in the environment are crucial for environmental protection and governance.
As a marker: 4-Dibenzothiopheneboronic acid can combine with certain environmental pollutants through specific chemical reactions to form compounds that are easy to detect and identify.This combination reaction not only improves the sensitivity of detection, but also helps to determine the type and concentration of pollutants.
For sensors: Based on its chemical properties, sensors can be developed for detecting environmental pollutants. These sensors can monitor the concentration of pollutants in the environment in real time, providing timely and accurate data support for environmental protection departments.
Environmental remediation and governance
In terms of environmental remediation and governance, it may play a role through the following ways:
Promote pollutant degradation: may act as a cofactor for certain microorganisms or enzymes, participating in the biodegradation process of pollutants. By promoting the biodegradation of pollutants, the concentration of pollutants in the environment can be significantly reduced, improving environmental quality.
As an adsorbent: it has a specific chemical structure and surface properties, and may exhibit adsorption capacity for certain pollutants. By using it as an adsorbent in environmental remediation, harmful substances such as heavy metal ions and organic pollutants in water can be effectively removed.
Participate in photocatalytic reactions: In photocatalytic reactions, it may act as a photosensitizer or catalyst to promote the photocatalytic degradation of pollutants. This degradation method has the characteristics of high efficiency and environmental protection, and is one of the research hotspots in the field of environmental remediation.
Environmental monitoring and assessment
Environmental monitoring and assessment are important components of environmental protection work. Possible roles in environmental monitoring and assessment include:
As an indicator: it may have specific responsiveness to certain environmental pollutants and can therefore be used as an indicator in environmental monitoring. By monitoring its concentration changes in the environment, it can indirectly reflect the presence and concentration level of pollutants.
Participate in risk assessment: In the process of environmental risk assessment, it can be used as one of the evaluation factors to assess the impact of pollutants on the environment and ecosystems. By comprehensively considering factors such as the nature, concentration, and other responsiveness of pollutants, the level of environmental risk can be more accurately assessed.
Environmental Education and Promotion
Environmental education and publicity are important means to raise public awareness of environmental protection and promote environmental protection work. Possible roles in environmental education and promotion include:
As a teaching case: In the teaching of related disciplines such as environmental science and chemistry, it can be used as one of the teaching cases to introduce its application and importance in environmental protection. Through case analysis, students can better understand the urgency and necessity of environmental protection.
For science popularization: In science popularization activities, its chemical properties and application examples can be used to popularize environmental protection knowledge to the public. Through vivid and interesting science popularization content, it can stimulate the public's interest and enthusiasm for environmental protection.
Plant growth regulators
Promote plant growth: Boron is one of the essential trace elements for plant growth and plays an important role in plant growth and development. Although it is different from ordinary boron fertilizers, the boron atoms it contains may promote plant growth through some mechanism. For example, it may participate in metabolic processes within plants, affecting the synthesis and transport of plant hormones, thereby regulating plant growth rate and morphology.
Improve crop stress resistance: Boron has a positive effect on improving crop stress resistance. It is possible to enhance the antioxidant capacity of crops, regulate cell osmotic pressure, and improve their resistance to adversity such as drought, salinity, and pests and diseases.
Soil improvement and fertilizer development
Soil boron supplement: For boron deficient soils, it can be used as a supplement to boron elements. By applying it to the soil, the boron content in the soil can be increased, the nutritional status of the soil can be improved, and sufficient boron elements can be provided for plants.
Improve fertilizer utilization efficiency: May interact with other nutrients in the soil to improve fertilizer utilization efficiency. For example, it may have a synergistic effect with nitrogen fertilizers, phosphorus fertilizers, etc., promoting the absorption and utilization of these nutrients by plants.
The redox method is a commonly used method for synthesizing 4-Dibenzothiopheneboronic acid. This method usually uses thiophenol as the raw material and obtains the product through oxidation reaction.
Preparation before synthesis:
Prepare the necessary raw materials and reagents such as thiophenol, oxidant, solvent, as well as experimental equipment such as reaction kettle, stirrer, thermometer, etc.
Oxidation reaction:
Dissolve thiophenol in a solvent, add an appropriate amount of oxidant, and begin the oxidation reaction. Oxidants can be peroxides, oxygen, nitric acid, etc., while solvents can be organic solvents such as alcohols, ethers, ketones, etc.
Separation and purification:
After the reaction is completed, the reaction solution is filtered to separate the solid catalyst and filtrate. Evaporate and concentrate the filtrate to obtain the crude product.
Reduction reaction:
Dissolve the crude product in a solvent, add an appropriate amount of reducing agent, and start the reduction reaction. The reducing agent can be metal hydride, alcohol based borate ester, etc., and the solvent is the same as above.
Crystallization drying:
After the reaction is completed, the reaction solution is filtered to separate the catalyst and filtrate. Evaporate and concentrate the filtrate to obtain crystals. Dry the crystal to obtain the final product.
Chemical equation:
C6H5SH+Oxidant → C6H4(OH)S(O)xH + H2O
(C6H4(OH)S(O)xH) + Reducer → C6H4(OH)B(OH)2 + By Product
Among them, C6H5SH represents thiophenol, Oxidant represents oxidant, C6H4 (OH) S (O) xH represents oxidation product, Reductor represents reducing agent, C6H4 (OH) B (OH) 2 represents 4 Dibenzothiopheneboronic acid, and By Product represents by-product.
Sulfonation method is a method for synthesizing the product, which uses benzene or diphenylsulfone as raw materials and obtains the target product through sulfonation reaction.
Preparation before synthesis:
Prepare the necessary raw materials and reagents such as benzene or diphenylsulfone, sulfonation agents, solvents, as well as experimental equipment such as reactors, stirrers, thermometers, etc.
Sulfonation reaction:
Dissolve benzene or diphenylsulfone in a solvent, add an appropriate amount of sulfonation agent, and start the sulfonation reaction. Sulfonating agents can be sulfuric acid, chlorosulfonic acid, etc., while solvents can be water, organic solvents, etc.
Separation and purification:
After the reaction is completed, cool the reaction solution to room temperature and filter to remove insoluble impurities. Adjust the pH value of the filtrate to neutral with alkaline solution, and then evaporate and concentrate to obtain the crude product.
Conversion into target product:
Dissolve the crude product in an organic solvent, add an appropriate amount of alkali or acidic catalyst, and carry out the conversion reaction. The catalyst can be sodium hydroxide, potassium hydroxide, or hydrochloric acid.
Crystallization drying:
After the reaction is completed, the reaction solution is filtered to separate the catalyst and filtrate. Evaporate and concentrate the filtrate to obtain crystals. Dry the crystal to obtain the final product.
Chemical equation:
C6H6 + SO3 → C6H4 (SO3H) + H2O
C6H4(SO3H) + 2NaOH → C6H4(OH)B(OH) 2 + Na2SO4 + 2H2O
Among them, C6H6 represents benzene, C6H4 (SO3H) represents benzenesulfonic acid, C6H4 (OH) B (OH) 2 represents product, and Na2SO4 represents sodium sulfate.
I. Foundational Stage (1950s–1980s)
Research on organoboron compounds began in the mid-19th century. A major breakthrough in modern organoboron chemistry came with the hydroboration reaction discovered by Herbert C.
Brown in the 1950s, which laid the groundwork for the synthesis of alkyl and alkenyl boronic acids. From the 1970s to the 1980s, the Suzuki-Miyaura coupling reaction was gradually perfected.
Aryl boronic acids became core reagents for constructing carbon-carbon bonds due to their high stability, excellent functional group tolerance and low toxicity, driving the systematic development of heterocyclic boronic acids.
As a sulfur-containing fused aromatic hydrocarbon, dibenzothiophene features high electron cloud density at the 4-position, making it a key site for functional modification and guiding the synthesis of 4-bromodibenzothiophene, the key precursor.
II. First Synthesis and Structural Verification (1990s)
In the early 1990s, with the maturation of the lithiation-borylation technology for halogenated heterocycles, 4-dibenzothiopheneboronic acid was first synthesized and reported.
The dominant synthetic route adopts 4-bromodibenzothiophene as the starting material. Under nitrogen protection at -78 °C, the raw material undergoes lithiation with n-butyllithium, followed by reaction with trimethyl borate.
The target product is obtained via acidification and column chromatography purification, with a yield of approximately 82%. Around 1995, the compound was registered with the CAS number 108847-20-7, marking its official inclusion in the chemical substance inventory.
Meanwhile, characterization techniques including NMR and XRD confirmed its molecular formula (C₁₂H₉BO₂S) and verified that the boronic acid group is attached to the 4-position of dibenzothiophene.
III. Application Expansion and Process Optimization (Early 21st Century to Present)
After 2000, surging demands in OLED materials, pharmaceutical intermediates and organic catalysis promoted its large-scale production. Between 2010 and 2015, the Miyaura borylation method (palladium-catalyzed, with bis(pinacolato)diboron as the boron source) gradually replaced the traditional lithiation route.
It features milder reaction conditions and broader functional group compatibility, making it suitable for industrial production. From 2015 to 2020, manufacturers in China, South Korea and other countries optimized the production process.
The adoption of the one-pot method simplified procedures and cut costs, turning this compound into a cost-effective fused-ring boronic acid building block. It is now widely applied in the synthesis of blue-light OLED materials, anti-tumor drug intermediates and organic ligands.
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