2-Methoxy-3-nitropyridine-5-boronic acid pinacol ester

2-Methoxy-3-nitropyridine-5-boronic acid pinacol esters are widely used in the field of organic synthesis.
One is often used to construct carbon-carbon bonds. In palladium-catalyzed coupling reactions, such as Suzuki-Miyaura, it can interact with halogenated aromatics or halogenated olefins. In this reaction, the borate group of 2-methoxy-3-nitropyridine-5-boronic acid pinacol esters can go through a series of complex oxidation addition, transmetallization and reduction elimination steps with halides in the presence of palladium catalysts and bases to form new carbon-carbon bonds. This reaction provides an effective way for the synthesis of biaryl and alkenyl aryl compounds with specific structures, which is of great significance in the fields of medicinal chemistry and materials science. For example, in the development of new drugs, the pyridine structure can be connected with other aromatic rings by this reaction to modify the activity and physicochemical properties of drug molecules.
Second, it is also a key intermediate in the multi-step synthesis strategy of nitrogen-containing heterocyclic compounds. Because of the different substituents such as methoxy and nitro on the pyridine ring, the characteristics of these substituents can be used to further modify the pyridine ring through an appropriate reaction sequence. Nitro can be reduced into amino groups, and methoxy can participate in nucleophilic substitution and other reactions, thereby constructing more complex nitrogen-containing heterocyclic systems, which facilitates the synthesis of alkaloids and natural product analogs.
Third, in the field of materials science, it may participate in the synthesis of materials with special optoelectronic properties. Through the coupling polymerization reaction with other monomers with conjugated structures, the formed polymers may have unique properties such as electron transport and luminescence, and are expected to be applied to optoelectronic devices such as organic Light Emitting Diodes (OLEDs) and solar cells.

The synthesis method of 2-methoxy-3-nitropyridine-5-boronic acid pinacol ester, although the ancient book "Tiangong Kaiwu" does not contain this substance, it can be deduced according to the current organic synthesis method. One of the common synthesis methods is to use 2-methoxy-3-nitropyridine as the starting material. A halogen atom is introduced before the 5th position of the pyridine ring. If a suitable halogenating agent is used, under suitable reaction conditions, the 5th position hydrogen is replaced by a halogen atom to generate 2-methoxy-3-nitro-5-halopyridine. In this halogenation reaction, it is necessary to pay attention to the reaction temperature, solvent and amount of halogenating reagent to achieve a higher yield.
Then, 2-methoxy-3-nitro-5-halopyridine is reacted with diphenacol borate, and with the help of palladium catalyst and base, boration occurs to form the target product 2-methoxy-3-nitropyridine-5-boronic acid pinacol ester. In the reaction system, the activity of palladium catalyst, the type and amount of base all have important effects on the reaction process and yield. For example, palladium acetate can be used as a catalyst, potassium carbonate is a base, and the reflux reaction can be heated in an organic solvent such as toluene.
Another way of synthesis is to start with the borate ester containing the pyridine structure, and introduce the methoxy group and nitro group through a series of functional group conversions. For example, the structure of pyridine boronic acid pinacol ester is first constructed, and then the nitro group is introduced at a suitable position through nitration reaction, and then the methoxylation reaction is carried out to introduce the methoxy group. 2-methoxy-3-nitropyridine-5-boronic acid pinacol ester can also be obtained. In this process, the control of the conditions of nitrification and methoxylation reactions is crucial, such as the ratio of mixed acid of nitric acid and sulfuric acid during nitrification, the reaction temperature, the methoxylation reagents and reaction solvents used during methoxylation, etc., all need to be carefully considered in order to achieve efficient synthesis.

2-Methoxy-3-nitropyridine-5-boronic acid pinacol ester, which is a commonly used reagent in the field of organic synthesis. Its physical and chemical properties are unique and have a profound impact on the process of organic synthesis and product characteristics.
Looking at its physical properties, it is mostly in a solid state under normal conditions. Due to the interaction between specific atoms and groups in the molecular structure, it is endowed with a certain melting point and boiling point. This substance has considerable solubility in organic solvents, such as common tetrahydrofuran, dichloromethane, etc. This solubility facilitates its uniform dispersion in organic reaction systems and participation in reactions.
As for chemical properties, the boric acid pinacol ester group is very active and can participate in a variety of classical organic reactions, such as the Suzuki coupling reaction. In such reactions, the group can form carbon-carbon bonds with halogenated aromatics or alkenes under the action of suitable catalysts and bases, so as to realize the construction of complex organic molecules. The methoxy group and the nitro group in the molecule also have chemical activities. Methoxy groups have a power supply effect, which can affect the electron cloud density of the pyridine ring, changing its reactivity and selectivity; nitro groups are strong electron-absorbing groups, which reduce the electron cloud density of the pyridine ring, making it more susceptible to attack by nucleophiles. The two coexist in the molecule and interact with each other, resulting in the compound exhibiting rich and diverse reaction characteristics under different reaction conditions, providing organic synthesis chemists with many strategies and possibilities for constructing new organic compounds.

The price of 2-methoxy-3-nitropyridine-5-boronic acid pinacol ester in the market is difficult to determine. The change in its price depends on many reasons.
The difficulty of preparing this product has a lot to do with it. If the preparation method is difficult, the materials required are rare and expensive, and the labor cost is voluminous, the price will be high. And the amount it needs is also a major factor in the market. If there are many people who want it, and the supply is small, the price will also increase; conversely, if the supply exceeds the demand, the price may be lower.
Furthermore, the price varies depending on the manufacturer. Probably well-known manufacturers, because of their fine craftsmanship and excellent quality, the price may be higher than ordinary. Looking at the market conditions in the past, the price of similar products often fluctuated between tens of yuan and hundreds of yuan per gram. However, this is only an approximate number. At present, the price of 2-methoxy-3-nitropyridine-5-boronic acid pinacol ester needs to be carefully observed in the current market situation and consulted with various suppliers to obtain a near-real price. The market situation is volatile, and various factors are intertwined, making it difficult to have a constant price.

2-Methoxy-3-nitropyridine-5-boronic acid pinacol ester, this is a chemical substance. Its storage conditions are crucial, related to the stability and quality of the substance.
When storing, the first environment is dry. Because the substance may be sensitive to moisture, it is easy to react with water and cause it to deteriorate. Therefore, it should be placed in a dry place, such as a sealed container equipped with a desiccant, to prevent water vapor from invading.
Temperature is also critical. It should be stored in a cool place, generally 2-8 ° C. High temperature may cause it to decompose and evaporate, damaging its chemical properties.
Furthermore, it is necessary to avoid direct light. The energy in the light or the chemical reaction of luminescence affects its structure and properties, so it should be stored in an opaque container or a dark environment.
At the same time, the storage place should be away from fire sources, heat sources and oxidants. If this substance encounters an open flame, hot topic or strong oxidant, it may be at risk of combustion or explosion.
In addition, the storage area should be well ventilated. Good ventilation can disperse volatile substances that may leak in time, reduce safety hazards, and help maintain a suitable storage environment.
Proper storage conditions ensure that 2-methoxy-3-nitropyridine-5-boronic acid pinacol ester maintains a good chemical state. Those who operate and store it should strictly abide by relevant regulations to ensure material quality and safety.