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What are the main uses of 3- (Boc-amino) pyridine?
3- (Boc-amino) pyridine is widely used in the field of organic synthesis. Its primary use is in medicinal chemistry. This compound can act as a key intermediate when creating new drug molecules. Due to its unique structure, it can combine with other functional groups through various chemical reactions, thus laying the foundation for the construction of complex and biologically active molecular structures.
In peptide synthesis, 3- (Boc-amino) pyridine also has important functions. The preparation of peptides often requires protection and deprotection steps to ensure the correct linking of amino acids. The tert-butoxycarbonyl (Boc) of this compound can be used as an amino protecting group, which exists stably under specific reaction conditions and can be easily removed when appropriate, without damaging the rest of the peptide structure.
Furthermore, in the field of materials science, 3- (Boc-amino) pyridine may participate in the synthesis of some functional materials. The combination of its pyridine ring and amino group imparts specific electronic properties and reactivity to the molecule, or can be used to prepare materials with special optical and electrical properties.
In chemical research and industrial production, 3- (Boc-amino) pyridine is often the starting material for the synthesis of more complex compounds. Chemists have made great contributions to the development of organic synthetic chemistry by carefully designing reaction routes, using their activity checking points, and constructing various target products through reactions such as nucleophilic substitution and coupling.
What are the synthesis methods of 3- (Boc-amino) pyridine
To prepare 3 - (Boc - amino) pyridine, there are two common methods.
First, 3 - amino pyridine is used as the starting material. This is because 3 - amino pyridine has high amino activity and can react with Boc anhydride (di-tert-butyl dicarbonate) under suitable conditions. Usually, in the presence of organic bases such as triethylamine and pyridine, the two react in organic solvents such as dichloromethane and tetrahydrofuran. The role of the base is to neutralize the acid formed by the reaction, so that the reaction equilibrium shifts in the direction of the product. For example, 3-aminopyridine is dissolved in an appropriate amount of dichloromethane, and a mixed solution of Boc anhydride and triethylamine is slowly added dropwise under an ice bath. After dropping, the reaction is heated to room temperature and stirred. The reaction progress is monitored by TLC (thin-layer chromatography). When the raw material point disappears, the reaction is as expected. Subsequently, the reaction solution is washed with water, dried, and the solvent is removed by rotary evaporation, and then separated and purified by column chromatography to obtain pure 3- (Boc-amino) pyridine.
Second, the pyridine ring is modified with a derivative containing the pyridine ring as the starting material, and a suitable substituent is introduced. Then it is converted into 3-aminopyridine through a series of reactions, and then reacts with Boc anhydride. If 3-halogenated pyridine is used as raw material, nucleophilic substitution reaction occurs with nucleophilic reagent first, amino precursor is introduced, 3-aminopyridine is obtained by reduction and other steps, and then the target product 3- (Boc-amino) pyridine is prepared according to the above reaction method with Boc anhydride. Although this approach is a little complicated, it may have unique advantages in raw material selection or reaction condition optimization.
What are the physical properties of 3- (Boc-amino) pyridine
3- (Boc-amino) pyridine is one of the organic compounds. Its physical properties are quite important, let me tell them one by one.
Looking at its morphology, under room temperature and pressure, this substance is often in a solid state. Its color is mostly white to off-white powder, with fine texture and purity.
The melting point is within a certain range, and this property is of great significance for the identification and purification of compounds. Due to the different melting points of different compounds, this can determine its purity and provide a basis for the separation of mixtures.
In terms of solubility, 3- (Boc-amino) pyridine has different behaviors in common organic solvents. In some organic solvents, such as dichloromethane, its solubility is still good, and it can be uniformly dispersed to form a clear solution. This property is convenient for various chemical reactions to be carried out in this medium, so that the reactants are fully contacted and the reaction process is accelerated. In water, its solubility is poor and insoluble. This is due to the weak interaction between the groups contained in it and the water molecules due to the characteristics of its molecular structure.
Furthermore, its density is also an important physical property. Although the exact value needs to be determined by professional instruments, the size of the density affects its distribution in different media. It is a factor that cannot be ignored in many fields such as chemical production and material separation. < Br >
also has a boiling point. Although the exact boiling point needs to be determined by rigorous experiments, the boiling point depends on its change during heating, and is a key consideration for separation operations such as distillation.
The physical properties of this compound are the cornerstone in organic synthesis, drug development and other fields. Chemists can choose suitable reaction conditions according to its melting point, solubility and other properties, optimize the synthesis route, and improve the purity and yield of the product. In drug development, physical properties also affect the preparation process and bioavailability of drugs, which is crucial.
What are the storage conditions for 3- (Boc-amino) pyridine?
3- (Boc-amino) pyridine is an important compound in organic chemistry. Its storage conditions are crucial to its stability and quality.
This compound should be stored in a cool, dry and well-ventilated place. In a cool environment, the temperature can not be too high, and high temperature often causes the compound to decompose and deteriorate. Generally speaking, the temperature should be controlled between 2-8 ° C. This temperature range can effectively slow down the rate of molecular movement and reduce the possibility of chemical reactions.
A dry environment is also indispensable. The moisture in the air is easy to interact with the compound, or cause adverse changes such as hydrolysis. Therefore, the storage place should try to maintain a low humidity. Desiccants, such as anhydrous calcium chloride, silica gel, etc., can be used to absorb water vapor in the environment and ensure that the atmosphere in which the compound is located is dry.
Well ventilated can allow possible volatile impurities to dissipate in time without accumulating and affecting the quality of the compound. At the same time, storage containers should also be selected carefully. Glass bottles or plastic bottles with good sealing performance should be used. Glass bottles are chemically stable and not easy to react with compounds; plastic bottles are light in weight and have certain impact resistance. And the container should be clearly marked, clearly indicating the name, specification, storage date and other information of the compound for management and access.
During the use process, strict operating procedures should also be followed to minimize the contact time between the compound and air and moisture, and seal it back into place immediately after use, so that 3 - (Boc-amino) pyridine can be properly preserved and its performance can be maintained for a long time.
What are the common side reactions of 3- (Boc-amino) pyridine in the reaction?
In the reaction of 3- (Boc-amino) pyridine, there are three common side reactions. One is the removal of the Boc group. Although the Boc group is a protective group of the amino group, it is easy to remove under certain conditions. If there is a strong acidic or basic environment in the reaction system, it can cause the Boc group to leave. For example, in the case of strong acids such as hydrochloric acid, sulfuric acid, etc., or strong bases such as sodium hydroxide, potassium hydroxide, Boc groups or hydrolysis to generate tert-butanol and free amino groups. The second is the electrophilic substitution reaction of the pyridine ring. The pyridine ring has a certain electron cloud density, and under certain conditions, it is vulnerable to attack by electrophilic reagents. In the case of halogenated reagents, halogenated reactions can occur on the pyridine ring to form halogenated pyridine derivatives. This reaction check point may vary depending on the electronic effect of the substituents on the pyridine ring, and is commonly found in the 2-, 4-, and 6-positions of the pyridine ring. The third is the further reaction of the amino group. Although the amino group of 3- (Boc-amino) pyridine is protected by Boc, under certain conditions, when the protection is incomplete or the reaction conditions are severe, the amino group can participate in the reaction. In case of acylation reagents, the amino group may be acylated to form amide by-products. Or in case of alkylation reagents, an alkylation reaction can occur to obtain alkylation products. Such side reactions must be treated with caution in organic synthesis. By optimizing reaction conditions, selecting appropriate reagents and reaction sequences, side reactions can be effectively suppressed and the yield and purity of the target product can be improved.