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What is the chemical structure of 2-isopropoxy-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyridine?
This substance is named 2-isopropoxy-5- (4,4,5,5-tetramethyl-1,3,2-dioxyboron heterocyclopentane-2-yl) pyridine, and its chemical structure is as follows:
The pyridine ring is the core skeleton of this compound. This is a six-membered nitrogen-containing heterocycle with unique properties and is widely used in many fields of organic synthesis and medicinal chemistry. The second position of the pyridine ring is connected to the isopropoxy group. The isopropoxy group is composed of an oxygen atom connected to an isopropyl group. The isopropyl group is an alkyl group structure with a branched chain. Its introduction will affect the physical and chemical properties of the compound, such as enhancing the lipid solubility of the molecule, which in turn affects its solubility in different solvents and its interaction with other molecules.
The fifth position of the pyridine ring is connected to 4,4,5,5-tetramethyl-1,3,2-dioxyboronheterocyclopentane-2-yl. This structure is a five-membered cyclic boroxy structure. The boron atom is connected to two oxygen atoms and two carbon atoms, and the fourth and fifth positions on the ring are connected with two methyl groups. The structure of boroxyheterocyclopentane has a wide range of uses in organic synthesis, and is often used as an organoboron reagent to participate in various reactions, such as the Suzuki reaction, which can realize the construction of carbon-carbon bonds, which is of great significance in the fields of drug research and development, materials science, etc. The existence of many methyl groups increases the steric resistance and electronic effect of this part of the structure, and has an effect on the reactivity, stability and binding ability of the whole compound with other molecules. In summary, the unique chemical structure of 2-isopropoxy-5- (4,4,5,5-tetramethyl-1,3,2-dioxoboropentane-2-yl) pyridine endows it with potential application value in organic synthesis and related fields.
What are the main uses of 2-isopropoxy-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyridine?
2-Isopropoxy-5- (4,4,5,5-tetramethyl-1,3,2-dioxoboran-2-yl) pyridine, which is a crucial compound in the field of organic synthesis. Its uses are quite extensive, and let me tell them one by one.
First, in the field of pharmaceutical chemistry, it is often used as a key intermediate. In the synthesis path of many drugs, this compound needs to participate in the reaction and be transformed through specific steps to construct a molecular structure with specific pharmacological activities. Due to its unique chemical structure, specific groups can be introduced to optimize the physicochemical properties of drug molecules, such as solubility, stability, and affinity with targets, thus laying the foundation for the development of new drugs.
Second, it also has important applications in the field of materials science. For example, in the synthesis of organic optoelectronic materials, it can be used to prepare conjugated polymers or small molecule materials with specific functions. Such materials show great potential in the fields of organic Light Emitting Diodes (OLEDs), organic solar cells, etc., which can improve the photoelectric properties of materials, improve device efficiency and stability.
Third, in the field of organic synthetic chemistry, it participates in many boronation reactions as a boron-containing reagent. Through coupling reactions with other organic halides or electrophilic reagents, such as the Suzuki-Miyaura coupling reaction, carbon-carbon bonds can be efficiently formed, providing a convenient and effective strategy for the synthesis of complex organic molecules, enabling chemists to synthesize organic compounds with diverse structures.
What are the synthesis methods of 2-isopropoxy-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyridine?
To prepare 2-isopropoxy-5- (4,4,5,5-tetramethyl-1,3,2-dioxyboron heterocyclopentane-2-yl) pyridine, the common synthesis methods are as follows:
First, 2-chloro-5-bromopyridine is used as the starting material. First, 2-chloro-5-bromopyridine and isopropanol are heated in the presence of a base (such as potassium carbonate) and a suitable catalyst (such as cuprous iodide and corresponding ligands) to undergo a nucleophilic substitution reaction, and the chlorine atom is replaced by isopropoxy to generate 2-isopropoxy-5-bromopyridine. Subsequently, this product is reacted with diphenacol borate under the action of palladium catalyst (such as tetra (triphenylphosphine) palladium) and base (such as potassium acetate) in an organic solvent (such as 1,4-dioxane), and the bromine atom is replaced by (4,4,5,5-tetramethyl-1,3,2-dioxyboronheterocyclopentane-2-yl) to obtain the target product 2-isopropoxy-5- (4,4,5,5-tetramethyl-1,3,2-dioxane-2-yl) pyridine.
Second, take 2-hydroxy-5-bromopyridine as the starting material. The starting material is first etherified with an isopropylation reagent (such as isopropyl halide, like isopropyl bromide) under the action of a base (such as sodium hydride), and the hydroxyl group is replaced by isopropoxy to obtain 2-isopropoxy-5-bromopyridine. The subsequent steps are consistent with the reaction starting from 2-isopropoxy-5-bromopyridine in the first method, that is, it reacts with the diptyl dinacol borate in the presence of palladium catalysis and base to obtain the target product.
Another way is to use 2-isopropoxy-5-iodopyridine as raw material, react with pinacol borane in a suitable solvent under the action of palladium catalyst and base, and the iodine atom is replaced by (4,4,5,5-tetramethyl-1,3,2-dioxyboron heterocyclopentane-2-yl) to obtain 2-isopropoxy-5- (4,4,5,5-tetramethyl-1,3,2-dioxyboron heterocyclopentane-2-yl) pyridine. Different methods have their own advantages and disadvantages, and they need to be selected according to the actual situation, such as the availability of raw materials, the difficulty of reaction conditions, and the cost.
What are the physical properties of 2-isopropoxy-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyridine?
2-Isopropoxy-5- (4,4,5,5-tetramethyl-1,3,2-dioxyboron-heterocyclopentane-2-yl) pyridine, which is a compound commonly used in the field of organic synthesis. Its physical properties are related to many aspects, let me tell them one by one.
Looking at its appearance, it is mostly a white to almost white solid at room temperature and pressure. This color and morphology are quite common among many organic compounds, which is convenient for researchers to identify initially. The determination of its melting point is crucial for the identification of purity and understanding of thermal stability. After experimental investigation, the melting point of this compound is within a specific range, and the specific value may vary slightly depending on different experimental conditions. This melting point property is of great significance in organic synthesis steps, such as crystallization and separation.
When it comes to solubility, the compound shows a certain preference in organic solvents. Common organic solvents such as dichloromethane, N, N-dimethylformamide (DMF), etc., have good solubility to it. In dichloromethane, it can quickly disperse and dissolve to form a homogeneous solution. This property allows it to fully participate in the reaction in the organic reaction using dichloromethane as the reaction medium to ensure the smooth progress of the reaction. However, the solubility in water is poor, which is related to the large proportion of hydrophobic groups in the molecular structure.
From the perspective of stability, under normal environmental conditions, without the influence of special chemical reagents or extreme physical conditions, this compound can remain relatively stable. However, it should be noted that the boroxide heterocyclic structure it contains has decreased stability in strongly acidic or strongly alkaline environments, or due to chemical reactions such as chemical bond breaking and recombination.
In addition, although the physical properties of the compound such as density and vapor pressure are relatively less concerned in daily research, they are also of great significance in large-scale industrial production and specific physical and chemical processes. Density data are helpful for determining the proportion of materials in the reaction system and product quality control; vapor pressure is related to the volatilization performance of compounds at different temperatures, which affects the choice of reaction conditions and the separation and purification of products.
The above physical properties are indispensable factors to consider when applying this compound in organic synthesis, medicinal chemistry and other fields, helping researchers to better design reaction paths, optimize experimental conditions and control product quality.
What should be paid attention to when storing and transporting 2-isopropoxy-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyridine?
2-Isopropoxy-5- (4,4,5,5-tetramethyl-1,3,2-dioxyboron heterocyclopentane-2-yl) pyridine, when storing and transporting, need to pay attention to many matters.
First, temperature has a great influence. This compound is more sensitive to temperature, and high temperature can easily cause it to decompose or deteriorate. Therefore, when storing, it should be in a cool place, and the temperature should be controlled within a specific range. For example, it is usually appropriate to refrigerate at 2-8 ° C. This can keep its chemical properties stable and reduce the risk of decomposition. During transportation, it is also necessary to ensure a stable temperature and avoid exposure to the sun or high temperature environment.
Second, the humidity should not be underestimated. Moisture easily reacts with the compound, causing it to fail. Therefore, when storing, it needs to be placed in a dry place, and a desiccant can be used to assist in maintaining a dry environment. During transportation, the packaging must be tight to prevent moisture from invading. Moisture-proof packaging materials can be used, such as sealed plastic bags, aluminum foil bags, etc.
Third, light is also a key factor. This substance is affected by light, or it may cause luminescent chemical reactions, which damage its structure and properties. Therefore, storage should be protected from light, such as brown bottles, or placed in a dark place. When transporting, it should also avoid direct light exposure, and the packaging can have light-shielding properties.
Fourth, the packaging should be solid and reliable. Because it is a chemical substance, or has a certain risk, improper packaging is prone to leakage, causing safety problems. Packaging materials should be resistant to impact and corrosion, to ensure that they are not damaged or leaked during storage and transportation.
Finally, the marking must be clear. The name, nature, storage conditions and precautions of the compound should be clearly marked on the packaging, so that relevant personnel can quickly know its characteristics when handling, and take correct measures to ensure the safety of storage and transportation.