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What are the main uses of 2-bromo-5-aminopyridine?
2-Bromo-5-aminopyridine, Chinese name 2-bromo-5-aminopyridine, has a wide range of uses and is crucial in many fields.
First, in the field of medicinal chemistry, it is often a key intermediate for the synthesis of various drugs. Due to its unique activity of pyridine ring structure and amino and bromine atoms, it can be cleverly spliced with other molecular fragments through various chemical reactions to construct compounds with complex structures and specific pharmacological activities. For example, it can be used to create antibacterial drugs, which can interfere with the normal physiological metabolic process of bacteria by precisely binding to specific targets in bacteria, so as to achieve antibacterial effect; or it can be used to develop anti-tumor drugs, which participate in the signaling pathway of tumor cells and inhibit the growth and proliferation of tumor cells by virtue of their unique chemical structure.
Second, in the field of materials science, 2-bromo-5-aminopyridine can be used as an important raw material for the construction of new functional materials. The conjugated structure of the pyridine ring and the reactivity of amino and bromine atoms can enable it to participate in the polymerization reaction to prepare polymer materials with special photoelectric properties. Such materials may emerge in the field of organic Light Emitting Diodes (OLEDs), solar cells and other optoelectronic devices, contributing to the improvement of device performance. For example, in OLEDs, it may optimize the luminous efficiency and stability of materials, resulting in better display effects.
Third, in the field of organic synthetic chemistry, it is an extremely important reaction substrate. Bromine atoms can undergo nucleophilic substitution reactions, while amino groups can participate in a variety of condensation reactions and functional group conversions. Chemists can take advantage of these reaction characteristics to flexibly design and synthesize novel and complex organic compounds, which will contribute to the development of organic synthetic chemistry and help explore more organic molecules with unique properties and potential applications.
What are 2-bromo-5-aminopyridine synthesis methods?
To prepare 2-bromo-5-aminopyridine, there are three methods.
First, 5-aminopyridine is used as the starting material. First, a suitable brominating agent, such as bromine or N-bromosuccinimide (NBS), is used in a suitable solvent, such as dichloromethane, at low temperature and in the presence of a catalyst, such as iron powder or iron tribromide. This is because the amino group is an ortho-para-locator. Although the ortho-locator will also be formed during bromination, the target product can be obtained by subsequent separation. The reaction mechanism is electrophilic substitution, and the electron cloud density of the pyridine ring is higher when the bromine positive ion attacks the pyridine ring.
Second, 2-bromo-pyridine is used as the starting material. First, it is nitrified with suitable nitrifying reagents, such as the mixed acid of concentrated nitric acid and concentrated sulfuric acid, in a specific temperature range, to obtain 2-bromo-5-nitropyridine. In this step, the electron cloud distribution characteristics of the pyridine ring are used, and the nitro group mainly enters the 5-position. Subsequently, the nitro group is reduced to an amino group with a reducing agent, such as iron and hydrochloric acid, or hydrogen and a suitable catalyst (such as palladium carbon), to obtain 2-bromo-5-aminopyridine.
Third, start from pyridine. First protect the pyridine ring in an appropriate way to prevent subsequent overreaction. After that, bromination and nitrification are carried out in sequence, and then the target product is obtained through deprotection and nitro reduction steps. Although this route step is complicated, it can be finely regulated according to the reaction conditions of each step to improve the yield and purity.
Each method has its own advantages and disadvantages. The actual synthesis needs to be carefully selected according to the availability of raw materials, cost, reaction conditions and the purity requirements of the target product.
What are the physical properties of 2-bromo-5-aminopyridine?
2-Bromo-5-aminopyridine is an organic compound with unique physical properties. Looking at its properties, it is mostly solid under normal conditions. Due to the strong intermolecular force, its structure is stable and it exists in a solid state. As for the melting point, it is about 80 to 85 degrees Celsius. Within this temperature range, the molecule can break free from the lattice binding and gradually melt from the solid state to the liquid state.
When it comes to solubility, it has good solubility in common organic solvents such as ethanol and dichloromethane. Ethanol contains hydroxyl groups, and 2-bromo-5-aminopyridine can form hydrogen bonds to increase its miscibility; dichloromethane has appropriate polarity and adapts to the intermolecular force of the compound, so it is soluble. However, in water, its solubility is poor, because its molecular polarity is limited, and the force between water molecules cannot match the hydrogen bond between water molecules, so it is difficult to dissolve.
The density of 2-bromo-5-aminopyridine is about 1.65g/cm ³, which is heavier than water. Due to the large amount of bromine atoms in the molecule, the weight per unit volume increases. Its appearance is often white to light yellow. This color is due to the absorption and reflection characteristics of the molecular structure. The pyridine ring and amino and bromine atoms in the molecule work together to absorb or scatter light of specific wavelengths.
In addition, the compound is volatile to a certain extent. Although the degree of volatilization is not high, some molecules can escape into the gas phase under open system, appropriate temperature and ventilation conditions. Due to its above physical properties, it is widely used in the field of organic synthesis. It can be used as a key intermediate to participate in a variety of organic reactions and synthesize complex organic compounds.
What are the chemical properties of 2-bromo-5-aminopyridine?
2-Bromo-5-aminopyridine is an organic compound with unique chemical properties. Its structure contains bromine atoms and amino groups attached to the pyridine ring, and this structure gives it a variety of chemical activities.
First of all, its alkalinity, the amino group has lone pair electrons, making 2-bromo-5-aminopyridine weakly basic. In an acidic environment, the amino group can be protonated to form positively charged ions, improving the water solubility of the compound. This property is of great significance in pharmaceutical chemistry because it can improve the solubility and bioavailability of drugs.
In nucleophilic substitution reactions, bromine atoms are good leaving groups. In case of nucleophiles, such as alkoxides, amines, etc., bromine atoms are easily replaced to form new carbon-heteroatomic bonds. For example, the corresponding ether compounds can be obtained by reacting with alkoxides, which are important steps in organic synthesis and can be used to prepare complex organic molecules.
In addition, the amino group of 2-bromo-5-aminopyridine has nucleophilic properties. It can react with electrophilic reagents such as acyl halide and acid anhydride to form amide bonds. This reaction is widely used in the synthesis of drugs, natural products and materials containing amide structures. Pyridine ring itself has certain aromaticity and stability, which affects the distribution and reactivity of molecular electron clouds. Under appropriate conditions, pyridine rings can undergo electrophilic substitution reactions. Although the activity is lower than that of benzene rings, rational selection of reagents and conditions can still achieve specific position substitution and expand the diversity of molecular structures.
The redox properties also need to be paid attention to. Under specific conditions, 2-bromo-5-aminopyridine may participate in redox reactions. Amino groups can be oxidized to nitro groups or other oxidation states, and bromine atoms can be removed by reduction. Such redox reactions provide a way to adjust the electronic structure and chemical properties of compounds, and have potential applications in organic synthesis and materials science. In summary, 2-bromo-5-aminopyridine is rich in chemical properties and is an important intermediate in organic synthesis, drug development and other fields.
What is the price range of 2-bromo-5-aminopyridine in the market?
2-Bromo-5-aminopyridine is on the market, and its price range is difficult to determine. The change in price is affected by many factors.
The first to bear the brunt is its purity. For high purity 2-bromo-5-aminopyridine, the preparation process must be more complicated, and the cost is also high, so the price should be high. If the purity is slightly lower, although the preparation is slightly easier, the use or limited, the price will also drop.
Secondly, the difference between manufacturers also leads to price differences. Large factories often have economies of scale, mature production processes, cost or controllable, and price may have advantages. Small factories have high costs and high prices due to low output and poor technology.
Furthermore, the state of market supply and demand has a great impact on prices. If demand is strong and supply is limited, prices will rise; on the contrary, if supply exceeds demand, prices will fall.
Again, fluctuations in raw material prices are also related to the cost and selling price of 2-bromo-5-aminopyridine. If the price of raw materials rises, the price of the product will also rise; if the price of raw materials falls, the price of the product may fall.
According to past market conditions, the price per gram may range from tens of yuan to hundreds of yuan. However, this is only a rough estimate. To know the exact price, you must consult various chemical suppliers in detail and pay attention to market changes in real time to obtain the current exact price range.