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Propylboronic acid, CAS 17745-45-8, molecular formula C3H9BO2, is composed of four elements: carbon (C), hydrogen (H), boron (B), and oxygen (O). Its molecular weight is 87.9134 grams per mole, which plays an important role in determining its purity, measuring chemical reactions, and predicting its reaction performance. The appearance is white to light yellow crystalline powder, which is soluble in organic solvents such as methanol and acetone.
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Chemical Formula |
C3H9BO2 |
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Exact Mass |
88.07 |
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Molecular Weight |
87.91 |
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m/z |
88.07 (100.0%), 87.07 (24.8%), 89.07 (3.2%) |
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Elemental Analysis |
C, 40.99; H, 10.32; B, 12.30; O, 36.40 |
This solubility characteristic is of great significance for chemical reactions, separation and purification operations. At the same time, its solubility in water is low, which helps to separate the aqueous and organic phases when needed. Can be used to prepare some high-performance coatings and inks. These coatings and inks have excellent weather resistance, water resistance, wear resistance, and other properties, and can be widely used in fields such as construction, automotive, and printing.
Propylboronic acid is an important organic boron compound, and its synthesis methods mainly include the following:
This is a common method for synthesizing n-propylbornic acid. The specific steps are as follows:
Mix trimethoxyborane and propyl magnesium bromide in a suitable solvent.
Reacting at a certain temperature and pressure.
After the reaction is completed, n-propylbornic acid is obtained through appropriate post-processing steps such as washing, drying, etc.
The advantage of this method is that the reaction conditions are relatively mild and the purity of the product is high. However, it should be noted that temperature and pressure must be strictly controlled during the reaction process to avoid the generation of by-products.
In addition to trimethoxyborane, other boron reagents can also be used to react with propyl compounds to synthesize n-propylbornic acid. For example, boron reagents such as borane or borate esters can be used to react with propyl halides or propyl metal compounds.
The specific synthesis method may vary depending on the boron reagent and propyl compound used. Therefore, in practical operation, it is necessary to choose an appropriate synthesis method based on specific reaction conditions and the properties of reactants.
In recent years, with the development of catalytic technology, more and more researchers have begun to explore the synthesis of n-propylbornic acid through catalytic reactions. This method usually has the advantages of mild reaction conditions, high yield, and good selectivity.
For example, palladium catalyst can be used to catalyze the coupling reaction between propyl halide and boronic acid ester to synthesize n-propyl boronic acid. In addition, other metal catalysts or organic catalysts can also be used to catalyze the reaction.
It should be noted that the selectivity and yield of catalytic reactions are often influenced by factors such as catalyst type, reaction conditions, and reactant concentration. Therefore, in practical operation, strict screening and optimization of catalysts and reaction conditions are required.
In addition to the common synthesis methods mentioned above, there are other methods that can be used to synthesize n-propylbornic acid. For example, n-propylbornic acid can be synthesized by reacting lithium propyl with boronic acid esters; The compound can also be prepared by reacting propyl Grignard reagent with boric acid.
The choice of these methods depends on the specific reaction conditions and the properties of the reactants. In practical operation, it is necessary to choose the most suitable synthesis method based on experimental requirements and conditions.
Biological activity and mechanism of action
As an enzyme inhibitor:
Propylboronic acid is used as an enzyme inhibitor in some studies, which can inhibit the activity of specific enzymes. For example, in biochemical research, n-propylbornic acid may inhibit enzyme activity by binding to the active site of the enzyme, preventing normal binding and catalytic reactions between the enzyme and substrate. This inhibitory effect may contribute to the study of enzyme function, regulatory mechanisms, and the development of new enzyme inhibitor drugs.
Participate in the biosynthesis process:
In certain biosynthetic processes, n-propylbornic acid may participate as a key intermediate or cofactor in the reaction. For example, in the biosynthesis of siderophores, n-propylbornic acid may promote chelation and transport of iron ions by binding to related enzymes. This mechanism of action helps to reveal the regulatory mechanisms of complex metabolic pathways in organisms.
Affects cellular signal transduction:
N-Propylbornic acid may also exert biological activity by affecting cellular signaling pathways. Cellular signal transduction is an important way of information exchange between cells in organisms, involving the transmission and regulation of various signaling molecules. N-Propylbornic acid may alter the efficiency and direction of signal transduction by binding to key proteins in signaling molecules or signaling pathways, thereby affecting processes such as cell growth, differentiation, and apoptosis.
Antioxidant effect:
Some studies suggest that n-propylbornic acid may have antioxidant properties, capable of clearing free radicals or inhibiting oxidative stress responses. Free radicals are highly active molecules or atomic groups in living organisms that can damage biomolecules such as DNA, proteins, and lipids, leading to cell damage and disease occurrence. Propylbornic acid may reduce the concentration and activity of free radicals by binding to them or catalyzing antioxidant reactions, thereby protecting cells from oxidative damage.
The boron-assisted pathway in methane oxidation
Methane (CH₄), as the main component of natural gas, shale gas and combustible ice, has significant implications for the energy and chemical industries due to its efficient conversion. However, the C-H bond in methane molecules has a bond energy of up to 439 kJ/mol, and the molecular structure is symmetrical, which makes its activation require harsh conditions (such as high temperature and high pressure), and the products are prone to excessive oxidation to CO₂. In recent years, boron-containing catalysts (such as Propylboronic Acid) have provided new ideas for the selective oxidation of methane due to their unique electronic structure and controllable active sites.
Chemical Properties and Boron-Assisted Mechanism of Propylboronic Acid
Propylboronic Acid (C₃H₉BO₂) is formed by the covalent bonding of the methyl group (-CH₂CH₂CH₃) and the boronic acid group (-B(OH)₂). The boron atom has an empty p orbital, which can accept electron pairs to form coordination bonds, while the hydroxyl group (-OH) in the boronic acid group can dissociate and release protons (H⁺), giving it amphiprotic properties. In methane oxidation, Propylboronic Acid may assist the reaction through the following mechanism:
Free radicals initiation and stabilization
Methane oxidation usually requires free radical chain reactions, but the induction stage requires high activation energy. The boronic acid group of Propylboronic Acid can interact with trace amounts of NO, O₃ or halides (such as Cl⁻) through coordination or electron transfer to generate initial free radicals (such as ·CH₃, ·OH), shortening the induction period. For example, adding a small amount of HCl or Cl₂ to the BaCl₂ catalyst can increase the formaldehyde yield to 810 mg/L in a gas mixture.
Transition state stabilization
Methane oxidation to form methanol (CH₃OH) or formaldehyde (CH₂O) requires high-energy transition states (such as ·CH₃O, ·CH₂O₂). The boron atom of Propylboronic Acid can coordinate with the oxygen atom in the transition state through empty p orbitals, reducing the activation energy. Similarly, in the oxidation of ethane dehydrogenation, boron-based catalysts (such as B₂O₃/SiO₂) selectively activate the C-H bond to generate ethylene through the formation of -B-O-O-B- or -B-O-O-N- peroxide species.
Product selectivity control
Methane oxidation is prone to excessive formation of CO₂, requiring inhibition of deep oxidation. The boronic acid group of Propylboronic Acid can form hydrogen bonds or coordination bonds with the hydroxyl or aldehyde groups in the products (such as CH₃OH, CH₂O), preventing further oxidation through steric hindrance or electronic effects. For example, in the In₂O₃-supported Pd catalyst, oxygen vacancies and Pd atoms synergistically adsorb CH₄ and O₂ to form the CH₃O· intermediate, while the introduction of boron may further stabilize this intermediate and improve the selectivity to formaldehyde.
Experimental evidence of boron-assisted pathways in methane oxidation
Homogeneous oxidation system
In the pressurized homogeneous oxidation, the yield of methane conversion to methanol increases with pressure, but stabilizes beyond 300 atm. Adding Propylboronic Acid can stabilize the methanol intermediate through boron-oxygen coordination, reducing its decomposition into CO₂. For example, at 500 atm and 475°C, the methanol yield can reach 1.88 g/100 L, while the formaldehyde yield is only 0.027 g/100 L, indicating that boron-assisted may preferentially stabilize aliphatic product.
Heterogeneous catalytic system
Boron-containing materials (such as boron nitride, borate salts) exhibit unique activity in methane oxidation. Boron nitride (BN) nanosheets can adsorb CH₄ through edge boron sites and utilize N sites to activate O₂, generating ·OOH radicals that attack CH₄ to achieve low-temperature (<300°C) oxidation. Similarly, a catalyst modified with Propylboronic Acid may selectively activate the C-H bond of methane through boron-carbon interaction.
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Challenges and future directions
Although Propylboronic Acid shows potential in methane oxidation, its application still faces challenges:
The active site is not clear
The existence form of boron in the catalyst (such as isolated boron, boron-oxygen ring, borate ester) and its mechanism of action remain controversial. It is necessary to clarify the structure of the active center by combining in-situ spectroscopy (such as XAS, DRIFTS) and theoretical calculations (such as DFT).
Stability and regeneration
Propylboronic Acid is prone to boron loss or polymerization in high-temperature or oxidative environments, resulting in catalyst deactivation. It is necessary to develop strong boron-adsorbent interactions (such as B-O-Si, B-O-Ti) or self-repair mechanisms (such as dynamic borate ester bonds) to improve stability.
Sustainable application
Current research is mostly limited to laboratory scale. It is necessary to optimize the catalyst preparation process (such as atomic layer deposition, sol-gel method) and design continuous flow reactors to achieve industrial application.
Propylboronic Acid, a crucial alkyl boronic acid, was discovered in the early 20th century, amid the initial exploration of organoboron compounds. Its discovery is closely linked to the gradual development of organoboron chemistry, which began with the pioneering work of English chemist Edward Frankland in 1860, who first reported the preparation of organoboron compounds using boron halides and zinc alkyls, laying the foundation for subsequent research on alkyl boronic acids.
In 1909, Russian chemists Khotensky and Melamed made a breakthrough: they successfully prepared and isolated several alkyl boronic acids, including methyl, ethyl, propyl, isobutyl, and isoamyl boronic acids, using the Grignard reaction-a landmark method that enabled the synthesis of various alkyl boronic acids for the first time. This marked the formal discovery of propylboronic acid, though its initial characterization was relatively simple, focusing only on basic preparation and preliminary properties.
Subsequent decades saw incremental improvements in the understanding and synthesis of propylboronic acid. In 1930, Konig and Scharrnbeck further optimized the synthesis process by using the Grignard reaction with boron trichloride, improving the yield and purity of propylboronic acid and confirming its heat and moisture sensitivity-a key characteristic of alkyl boronic acids. Initially, propylboronic acid received little attention due to limited applications, but its discovery paved the way for the development of higher alkyl boronic acids and expanded the scope of organoboron chemistry, laying a foundation for its later applications in organic synthesis, pharmaceuticals, and electrochemistry.
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