2-Bromo-4-pyridine carboxylic acid tert-butyl ester

Tert-butyl 2-bromo-4-pyridyl carboxylate is a crucial compound in the field of organic synthesis. It has a wide range of uses. In the field of medicinal chemistry, it is often used as a key intermediate and participates in the construction of many bioactive compounds. The structure of the pyridine ring and carboxyl tert-butyl ester endows it with unique reactivity and spatial structure, and plays an indispensable role in the synthesis of drug molecules containing pyridine skeletons.
In the field of materials science, tert-butyl 2-bromo-4-pyridyl carboxylate is also useful. Through specific chemical reactions, it can be introduced into the main chain or side chain of polymer materials to improve the properties of materials, such as solubility, thermal stability and optical properties. For example, through polymerization, polymeric materials with special functions can be prepared, which are suitable for optoelectronic devices, sensors and other fields.
In addition, in the study of organic synthesis methodology, this compound is often used as a model substrate to explore new reaction pathways and catalytic systems. The functional group of its bromine atom and carboxyl tert-butyl ester can initiate various classical organic reactions, such as nucleophilic substitution reactions and metal-catalyzed coupling reactions. Researchers can develop more efficient and green organic synthesis methods by in-depth study of their reaction properties, and promote the development of organic chemistry.
In conclusion, tert-butyl 2-bromo-4-pyridyl carboxylate has important application value in many fields such as drug development, materials science and organic synthesis methodology due to its unique structure and reactivity. It is an indispensable and important compound in the field of organic chemistry.

There are several common methods for synthesizing tert-butyl 2-bromo-4-pyridinecarboxylate.
First, the target product can be obtained by bromination with tert-butyl 4-pyridinecarboxylate as the starting material. In this method, it is often necessary to select suitable bromination reagents. For example, N-bromosuccinimide (NBS) is used as a brominating agent. In organic solvents such as carbon tetrachloride, under heating or lighting conditions, NBS will gradually decompose to produce bromine free radicals, which will then react with specific positions on the pyridine ring of tert-butyl 4-pyridinecarboxylate to form 2-bromo-4-pyridinecarboxylate. The key to this reaction lies in the precise control of the reaction temperature, light intensity and the amount of NBS, because the reactivity of the pyridine ring and the selectivity of the substitution check point are affected by many factors. If the temperature is too high or the NBS is excessive, the byproducts of polybromide may be generated, resulting in a decrease in the purity of the target product.
Second, the esterification reaction between 2-bromo-4-pyridinecarboxylic acid and tert-butanol is carried out in the presence of dehydrating agent and catalyst. The commonly used dehydrating agent is dicyclohexyl carbodiimide (DCC), and the catalyst can be selected as 4-dimethylaminopyridine (DMAP). During the reaction, the carboxyl group of 2-bromo-4-pyridinecarboxylic acid and the hydroxyl group of tert-butanol are dehydrated under the action of DCC to form ester bonds, and DMAP can speed up the reaction rate and improve the reaction efficiency. After the reaction is completed, the products need to be separated and purified by means such as column chromatography to remove impurities such as unreacted raw materials and dicyclohexyl urea formed by DCC reaction.
Third, from pyridine, a series of reactions can be started by introducing carboxyl groups at the 4th position of the pyridine ring, and then introducing bromine atoms at the 2nd position, and finally converting the carboxyl groups into tert-butyl ester groups. Although there are many steps in this route, the selectivity and controllability of each step are relatively good. For example, first, pyridine is used as the substrate, and a suitable carboxyl precursor is introduced through electrophilic substitution reaction, and then converted into a carboxyl group through oxidation and other steps; then bromine atoms are introduced at the second position by bromination reaction; finally, the esterification reaction with tert-butanol is carried out to obtain the target product 2-bromo-4-tert-butyl pyridinecarboxylate. In this process, the optimization of reaction conditions at each step and the purification of intermediate products are crucial, which are related to the yield and purity of the final product.

Tert-butyl 2-bromo-4-pyridyl carboxylate is an organic compound. Its physical properties are quite important, and it is related to many chemical processes and practical applications.
Looking at its appearance, under room temperature and pressure, it is mostly white to light yellow crystalline powder. This color and morphology can be an important basis for the preliminary identification of the compound. Due to its crystalline characteristics, the powder has a uniform texture, fine particles, and may have a subtle luster flicker under light.
Melting point is also a key physical property. Its melting point is roughly in a specific temperature range, and this value is of great significance for the identification of compound purity. If the melting point of the sample is consistent with the theoretical value, the deviation is very small, indicating that the purity of the sample is quite high; conversely, if the melting point deviation is large, or the melting range is wider, it may mean that the sample contains impurities.
In terms of solubility, tert-butyl 2-bromo-4-pyridinecarboxylate exhibits different behaviors in organic solvents. Common organic solvents such as dichloromethane, chloroform, N, N-dimethylformamide (DMF) have good solubility. In dichloromethane, the compound can dissolve rapidly to form a clear and transparent solution, which makes dichloromethane often selected as a reaction solvent or for the extraction and separation of compounds. In water, its solubility is minimal, due to the large proportion of hydrophobic groups in the molecular structure of the compound, which makes it difficult to dissolve in the aqueous phase with strong polarity.
In addition, the density of the compound is also a specific value. This physical property is indispensable when it comes to solution preparation, reaction material measurement, etc. Knowing its density can accurately calculate the volume or mass of the desired compound to ensure that the chemical reaction proceeds as expected.
Its boiling point is also an inherent property. Under specific pressure conditions, it will reach the corresponding boiling point. The boiling point data is a key reference index in separation operations such as distillation and purification, whereby the compound can be effectively separated from the mixture. The physical properties of tert-butyl 2-bromo-4-pyridyl carboxylate, from appearance, melting point, solubility, density to boiling point, play a crucial role in chemical research, organic synthesis and related industrial production, providing an important basis for the identification, purification and application of compounds.

The chemical properties of tert-butyl 2-bromo-4-pyridyl carboxylate are stable to a certain extent. In this compound, although the bromine atom has a certain activity, the pyridine ring and tert-butyl ester group also have a significant impact on its overall stability.
The pyridine ring has an aromatic structure, and the conjugate system endows it with a certain stability. The presence of nitrogen atoms makes its electron cloud distribution unique, which affects the activity of surrounding groups. In the tert-butyl ester group, the tert-butyl group has a steric hindrance effect, which can prevent external reagents from approaching the ester group, thereby enhancing molecular stability.
However, the bromine atom, as a halogenated hydrocarbon part, can undergo nucleophilic substitution reactions In case of nucleophilic reagents, bromine ions may be replaced, which is its chemical activity. However, under generally mild conditions, if there are no suitable reagents and reaction conditions, tert-butyl 2-bromo-4-pyridinecarboxylate can maintain a relatively stable state.
If it is exposed to high temperature, strong acid and base or specific catalyst environment, its stability may be challenged. High temperature may cause the vibration of chemical bonds to intensify, reduce the activation energy of the reaction, and make the originally stable structure more susceptible to change. Under strong acid-base conditions, ester groups may undergo hydrolysis, and the pyridine ring may also be affected by acid and base, changing the distribution of electron clouds, which in turn affects the activity of bromine atoms.
In summary, the chemical properties of tert-butyl 2-bromo-4-pyridinecarboxylate are relatively stable under common mild conditions, but they may exhibit active reactivity under certain extreme conditions or under the action of certain reagents.

2-Bromo-4-pyridine carboxylic acid tert -butyl ester is a key intermediate in organic synthesis. It is in the market price range and varies due to many factors.
Bear the brunt, the purity of the product greatly affects the price. If the purity is extremely high, almost 99% or more, such a high-quality product, due to the need for more stringent purification processes in the production process, the cost will rise sharply, and the price will be quite high. The price per gram may reach several hundred yuan. On the contrary, if the purity is only about 95%, because the purification requirements are slightly lower, the cost will drop slightly, and the price will decline accordingly, or in the tens of yuan per gram.
Furthermore, the price of the following pair in the market has a significant impact. When the market demand for this compound is strong, such as when pharmaceutical companies develop specific drugs, the demand for it increases greatly, and the supply is limited, the price is bound to rise. On the contrary, if the market demand is low, and there are many manufacturers and sufficient supply, the price may be reduced to attract buyers in order to seek sales.
In addition, the preparation process and raw material costs also affect the price. If the preparation process is complicated, multi-step reactions and special reaction conditions are required, and the raw materials are expensive, it will lead to higher production costs, which will then push up the price of the product.
According to past market conditions and chemical product price fluctuations, the price of 2-Bromo-4-pyridine carboxylic acid tert-butyl ester is roughly between tens of yuan and hundreds of yuan per gram. However, the chemical market is constantly changing, and factors such as raw material prices, policies and regulations, and technological innovation can all cause its prices to fluctuate. Therefore, the actual price should be subject to real-time market quotations.