Cyclohexylboronic Acid CAS 4441-56-9

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Cyclohexylboronic acid is an organic boron compound with the chemical formula C6H13BO2, CAS 4441-56-9, The corresponding molar mass is 137.98 g/mol. Colorless to light yellow crystalline solid or powdery substance. Soluble in various organic solvents such as ether, dimethylformamide (DMF), dichloromethane, and chloroform. It has low solubility in water. It is a flammable substance that may ignite. Due to its unique performance, this product has a wide range of applications in various industries. In the enamel and ceramic industry, it is used to enhance the gloss and fastness of enamel products, and is also one of the components of glazes and pigments. It is used as an additive and flux in the pharmaceutical and metallurgical industries, especially boron steel, which has high hardness and good rolling ductility and can replace nickel steel. It has anti-corrosion properties and can be used as a preservative, such as wood anti-corrosion. It is used in metal welding, leather, photography, and other industries, as well as in the manufacturing of dyes, heat-resistant and fire-resistant fabrics, artificial gemstones, capacitors, and cosmetics. It can also be used as an insecticide and catalyst. It can be used as a boron containing trace element fertilizer in agriculture, which is effective for many crops and can increase the oil content of rapeseed. Due to its ability to produce various borides, it is widely used in industrial sectors and research institutions such as national defense.

Cyclohexylboronic Acid (CAS Number: 4441-56-9) is an organic boron compound with the molecular formula C₆H₁₃BO₂ and a molecular weight of 127.98 g/mol. Its structure is formed by directly connecting the cyclohexyl group (C₆H₁₁-) with the boronic acid group (-B(OH)₂), creating a stable six-membered ring structure.

Physical state: White to light yellow crystalline powder, with a purity typically ≥ 97% (some products contain a small amount of acid anhydride).

Solubility: Slightly soluble in water, but readily soluble in organic solvents (such as ethanol, methanol, dichloromethane, tetrahydrofuran, etc.). This property makes it easy to operate in organic synthesis.

Thermal stability: Melting point is 122-123℃, boiling point is approximately 252.4℃. It should be stored in an inert atmosphere (such as nitrogen or argon) to avoid moisture or oxidation.

The manufacturing of Cyclohexylboronic Acid mainly involves a boronic acidification reaction, which is achieved through the coupling reaction of cyclohexyl halides (such as bromides or chlorides) with borate esters (such as tri-isopropylborate). The following are the key steps:

Raw material preparation

Cyclohexyl bromide (C₆H₁₁Br): As the starting raw material, it needs to be of high purity to reduce side reactions.

Boric acid ester: Commonly used is tri-isopropylborate ((i-PrO)₃B), due to its high reactivity and ease of separation.

Catalyst: Palladium catalyst (such as tetrakis(triphenylphosphine) palladium (0)) is the core of the Suzuki coupling reaction, which can accelerate the formation of carbon-boron bonds.

Solvent: Usually, anhydrous tetrahydrofuran (THF) or dioxane is chosen to provide an inert reaction environment.

Reaction process

Coupling reaction: In an inert atmosphere, cyclohexyl bromide, boric acid ester, and palladium catalyst are added to the solvent, heated to reflux (about 80-100℃), and stirred for 12-24 hours. In this step, the palladium catalyst promotes the cross-coupling of cyclohexyl bromide and boric acid ester, generating the intermediate cyclohexylboronic acid.

Post-hydrolysis processing: After the reaction is completed, cool to room temperature, and add dilute hydrochloric acid (HCl) or water for hydrolysis, converting the boric acid ester into the target product Cyclohexylboronic Acid. During the hydrolysis process, the pH value needs to be controlled to avoid excessive acidification that leads to product decomposition.

Purification and drying

Extraction: Extract the reaction mixture with water and organic solvents (such as ethyl acetate) to separate the organic layer.

Concentration: Remove the solvent by vacuum distillation to obtain the crude product.

Re-crystallization: Dissolve the crude product in hot ethanol or methanol, slowly cool to room temperature, allowing crystals to precipitate. Repeat this step to further increase the purity to over 99%.

Drying: Dry at a low temperature (such as 40℃) under vacuum to avoid high temperature causing the decomposition of boronic acid.

Quality control

Purity detection: Confirm the purity through high-performance liquid chromatography (HPLC) or nuclear magnetic resonance (NMR).

Impurity analysis: Detect residual solvents, inorganic salts, and unreacted raw materials to ensure compliance with pharmaceutical or industrial standards.

Cyclohexylboronic Acid, due to its unique chemical properties, plays an important role in multiple fields:

Organic Synthesis

 

 

Suzuki Coupling Reaction: Acting as a boronic acid reagent, it reacts with aryl or alkenyl halides to efficiently form carbon-carbon bonds, which is a key step in the synthesis of drugs, pesticides, and functional materials.

Cross-coupling Reaction: Reacting with aromatic amines or alcohols to achieve selective functionalization, used for developing complex molecular structures.

Pharmaceutical Chemistry

 

 

Drug Intermediate: Used for synthesizing anti-cancer drugs, antiviral drugs, and neuroactive drugs, such as introducing cyclohexyl structures through Suzuki reactions to enhance the lipid solubility or biological activity of the drugs.

Targeted Therapy: As a ligand-modified drug molecule, it improves the targeting to specific cells or tissues.

Materials Science

 

 

Boric Acid Ester Polymers: Participating in the synthesis of boron-containing high-molecular materials, used for preparing heat-resistant, flame-retardant, or conductive polymers.

Nanomaterials: As a surface modifier, regulating the dispersibility or biocompatibility of nanoparticles.

Cyclohexyl boronic acid has a wide range of applications in the enamel and ceramic industries, and its unique structure and properties make it an indispensable raw material in these industries.

 

1. Enhance the gloss and firmness of enamel products

In the process of enamel manufacturing, it can significantly improve the glossiness and firmness of enamel products. Enamel products need to have good wear resistance and corrosion resistance during use, and the addition of this substance can significantly improve the hardness and durability of enamel glaze. Specifically, as one of the components of enamel, through its unique molecular structure, a dense glaze layer is formed during the enamel firing process, effectively preventing external factors from corroding the enamel surface and maintaining its long-lasting luster and firmness.

Example: Enamel kitchenware
In the manufacturing process of enamel kitchenware, it is widely used in the formula of enamel glaze. Enamel cookware needs to withstand various chemical and physical changes during high-temperature cooking, while maintaining a smooth and aesthetically pleasing surface. The addition of this substance makes the glaze of enamel kitchenware harder, more wear-resistant, and less prone to detachment, thereby extending the service life of the kitchenware.

 

2. Improve the thermal stability of enamel products

It also has good thermal stability and can maintain the stability of the glaze at high temperatures. During the enamel firing process, it can effectively reduce the thermal expansion coefficient of the glaze and minimize the shrinkage and cracking of the glaze surface during cooling. At the same time, it can also improve the thermal shock resistance of the glaze, making enamel products less prone to cracking when subjected to rapid cooling and heating changes.

Example: Enamel water heater liner
Enamel water heater liner is another important application of this substance in the enamel industry. The inner tank of a water heater needs to withstand the pressure and corrosion of high-temperature water while maintaining its smoothness and sealing. The addition of cyclohexylboronic acid makes the enamel glaze layer of the inner tank denser, harder, and has good thermal stability and corrosion resistance, thereby ensuring the safe use and long service life of the water heater.

 

1. Enhance the glossiness and hardness of ceramic glaze

It also plays a significant role in ceramic glazes. It can improve the glossiness and hardness of glaze, making the surface of ceramic products smoother and brighter. As a flux and network forming agent for glazes, it can form a glass phase at low temperatures, improving the refractive index and mechanical strength of glazes. At the same time, it can also reduce the viscosity and surface tension of the glaze, which is beneficial for the uniform distribution and rapid solidification of the glaze.

Example: Ceramic tableware
Ceramic tableware is one of the typical applications in the ceramic industry. Tableware needs to have good aesthetics and practicality, and the addition of cyclohexylboronc acid makes the glaze of ceramic tableware smoother, brighter, and less prone to wear and tear. This not only improves the ornamental value of the tableware, but also extends its service life.

 

2. Improve the weather resistance and durability of ceramic products

It can also improve the weather resistance and durability of ceramic products. Ceramic products need to withstand various environmental factors during use, such as wind, sun, rain, and erosion. The addition of cyclohexylboronc acid can significantly improve the weather resistance of ceramic products, enabling them to maintain good appearance and performance even under long-term exposure to harsh environments. At the same time, it can also improve the durability of ceramic products and extend their service life.

Example: Outdoor Ceramic Sculpture
Outdoor ceramic sculpture is another important application in the ceramic industry. Sculpture needs to withstand the erosion of various natural environments while maintaining its artistic value and ornamental value. The addition of this substance makes the glaze layer of outdoor ceramic sculptures harder, more wear-resistant, and has good weather resistance, thereby ensuring the long-term preservation and viewing effect of the sculptures.

 

1. As a co solvent and additive

Cyclohexyl boronic acid can also be used as a co solvent and additive in the manufacturing process of enamel and ceramics. It can promote the melting and uniform distribution of glaze, improve the fluidity and wettability of glaze. At the same time, it can also serve as an additive for certain special functions, such as improving the anti fouling and antibacterial properties of glazes.

Example: Antibacterial enamel toilet
Antibacterial enamel toilet is an innovative application in the enamel industry. By adding antibacterial agents such as this substance to the enamel glaze, the surface of the toilet has excellent antibacterial properties, which can effectively inhibit the growth and reproduction of bacteria, thereby maintaining the cleanliness and hygiene of the toilet.

 

2. As a component of glaze

It can also be directly used for producing glazes as one of the components of glazes. It can form a glaze layer with specific properties and functions through chemical reactions with other raw materials. This glaze layer not only has good aesthetics, but also meets specific usage needs, such as improving the hardness, wear resistance, corrosion resistance, etc. of ceramic products.

Example: High hardness ceramic floor tiles
High hardness ceramic floor tiles are an important application in the ceramic industry. By adding fluxing agents such as cyclohexylboronic acid and forming a network in the glaze, the glaze layer of the floor tile is made harder and more wear-resistant. This type of floor tile not only has excellent anti fouling and anti slip properties, but also can withstand large weight and impact forces, making it suitable for various commercial and household places.

1. What's the use of it?
It is mainly used in the Suzuki coupling reaction, efficiently connecting cyclohexyl to the molecule, and is a key step in the synthesis of drugs and materials.
2. How to save?
* Sealed, dry, refrigerated (at 2-8°C or -20°C).
* It is best to be protected by nitrogen gas.
* Avoid contact with air and moisture to prevent deterioration.
3. Common reasons for reaction failure?
* Boric acid degradation: This is the most common cause. Check if it is a white powder, and if it has become lumpy or discolored, it may have failed.
* Insufficient conditions: Ensure that the reaction system is devoid of water and oxygen (air needs to be replaced), and use an adequate amount of the appropriate base (such as sodium carbonate).
* Catalyst deactivation: The palladium catalyst may have failed. Try replacing it with a fresh catalyst.

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