3 Bromo 2 Bromomethyl Pyridine
pyridine pyrrole pyrazine piperidine piperazine

3-bromo-2-(bromomethyl)pyridine

    Specifications

    HS Code

    789099

    Chemical Formula C6H5Br2N
    Molecular Weight 250.92 g/mol
    Appearance Solid (Typically)
    Melting Point Data needed
    Boiling Point Data needed
    Solubility In Water Low solubility (Expected, due to non - polar nature of organic part)
    Solubility In Organic Solvents Soluble in common organic solvents like dichloromethane, chloroform
    Density Data needed
    Vapor Pressure Low (Expected for a solid at normal conditions)
    Flash Point Data needed
    Stability Stable under normal conditions, but may react with strong oxidizing agents

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    Frequently Asked Questions

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    What is the main use of 3-bromo-2- (bromomethyl) pyridine?
    3-Bromo-2- (bromomethyl) pyridine, which is an important intermediate in organic synthesis. In the field of organic chemistry, its use is quite extensive.
    First, it is often used to construct the structure of complex pyridine compounds. Pyridine rings are widely found in many natural products, drug molecules and functional materials. Through the activity of bromine atoms and bromomethyl groups on 3-bromo-2- (bromomethyl) pyridine, various functional groups can be introduced through nucleophilic substitution, coupling and other reactions to build pyridine derivatives with specific structures and functions. For example, nucleophilic substitution reactions with nucleophiles containing nitrogen, oxygen, sulfur, etc., form new carbon-heteroatomic bonds, laying the foundation for the synthesis of biologically active pyridine drugs.
    Second, it also has potential applications in materials science. By rationally designing the reaction, it is introduced into polymer materials or functional polymers as a structural unit, endowing the material with unique optical, electrical or chemical properties. Due to the rigid structure of the pyridine ring and the modifiability of the bromine atom, it may improve the stability, solubility and intermolecular interactions of the material.
    Third, in the field of medicinal chemistry, this is used as a starting material to synthesize molecules with pharmacological activity through multi-step reactions. Bromine atoms and methyl bromide can be used as a check point for subsequent reactions. After modification, it may enhance the interaction between drugs and targets, and improve the activity, selectivity and pharmacokinetic properties of drugs. In the development of many anti-cancer, anti-inflammatory, antibacterial and other drugs, such pyridine derivatives have shown potential application value.
    In short, 3-bromo-2- (bromomethyl) pyridine, with its unique structure and reactivity, plays a key role in many fields such as organic synthesis, materials science, and drug development, providing important basic raw materials for the creation of new compounds and functional materials.
    What are the synthesis methods of 3-bromo-2- (bromomethyl) pyridine
    The synthesis method of 3-bromo-2 - (bromomethyl) pyridine has been studied by many parties in the past, and the following is the common number method.
    First, 2-methylpyridine is used as the starting material. Shilling 2-methylpyridine and N-bromosuccinimide (NBS) in a suitable solvent, such as carbon tetrachloride, under the action of the initiator azobisisobutyronitrile (AIBN), light initiates the radical substitution reaction. Under these conditions, the hydrogen on the methyl group can be replaced by the bromine atom to form 2 - (bromomethyl) pyridine. However, there may be a mixture of ortho and para-substitution in the product, which needs to be carefully separated. Then, 2 - (bromomethyl) pyridine is reacted with bromine in the presence of an appropriate catalyst, such as iron powder or iron tribromide, for electrophilic substitution, so that the third position of the pyridine ring is introduced into the bromine atom, and 3 - bromomethyl - (bromomethyl) pyridine can be obtained. The reaction conditions of each step in this process need to be precisely controlled, and the separation and purification also need to be carefully operated.
    Second, pyridine is used as the starting material. First, pyridine is lithiated with n-butyl lithium at low temperature, and lithium atoms are introduced into the second position of the pyridine ring to form 2-lithium pyridine. Then, 2-lithium pyridine is reacted with zinc bromide to obtain 2-zinc pyridine. Then, 2-zinc pyridine is cross-coupled with bromomethyl bromide, and bromomethyl can be introduced into the second position of pyridine. After that, by a method similar to electrophilic substitution, bromine is introduced into the third position of the pyridine ring using bromine and a suitable catalyst to obtain the target product 3-bromomethyl pyridine. This route involves organometallic reagents, which have strict requirements on the anhydrous and anaerobic reaction environment and are difficult to operate.
    Third, start from 3-bromopyridine. First, 3-bromopyridine interacts with a strong base, so that the hydrogen at the second position of the pyridine ring is captured to form a carboanion. Then, the carboanion undergoes a nucleophilic substitution reaction with bromomethyl halide, and bromomethyl is introduced at the second position to obtain 3-bromomethyl-2 - (bromomethyl) pyridine. The key to this method lies in the selection of strong bases and the regulation of reaction conditions to prevent side reactions from occurring.
    All synthesis methods have advantages and disadvantages, and the choice needs to be weighed according to the actual availability of raw materials, reaction conditions, cost and product purity requirements.
    What are the physical properties of 3-bromo-2- (bromomethyl) pyridine
    3 - bromo - 2 - (bromomethyl) pyridine is an organic compound with unique physical properties and great significance for organic synthesis and other fields.
    This substance is mostly solid at room temperature, but the specific physical form may vary depending on purity and external conditions. Its melting point and boiling point data are crucial for the identification and separation of this substance. Although exact melting point data are not available at present, the melting points of many bromine-containing organic compounds are in a relatively specific range, or vary due to factors such as intermolecular forces and structures. Its boiling point also varies due to factors such as molecular weight and intermolecular forces. Bromine-containing groups usually increase the boiling point because the relative mass of bromine atoms is large and the intermolecular forces can be enhanced.
    3-bromo-2- (bromomethyl) pyridine is insoluble in water, because the molecule is an organic structure with weak polarity, while water is a strong polar solvent, according to the principle of "similar miscibility", so it is insoluble. However, it is soluble in common organic solvents, such as dichloromethane, chloroform, ether, etc. The weak polarity or non-polarity of the organic solvent is in line with the molecular structure of the compound, which is conducive to molecular dispersion.
    The density of the compound is greater than that of water. This property is very important when it involves liquid-liquid separation operations. It will be in the lower layer, which is convenient for separation and purification.
    In addition, 3-bromo-2- (bromomethyl) pyridine has a certain volatility. Although the volatility is not strong, in a poorly ventilated environment, its volatilized steam or air pollution should be paid attention to during operation. And because it contains bromine atoms, steam or irritating odor, it may be irritating to the respiratory tract, etc., protective measures should be taken during operation.
    What are the chemical properties of 3-bromo-2- (bromomethyl) pyridine
    3 - bromo - 2 - (bromomethyl) pyridine is also an organic compound. It has a halogenated pyridine structure, containing bromine atoms and bromomethyl groups, which endows it with unique chemical properties.
    First, because of its halogen atoms, nucleophilic substitution reactions can occur. Bromine atoms are highly active, and nucleophilic reagents such as alkoxides and amines can attack them. Bromine atoms leave to form new compounds. If reacted with alkoxides, ethers can be formed; when reacted with amines, amine-substituted products are produced. This is a common strategy for organic synthesis to build carbon-heteroatomic bonds.
    Second, bromine in bromomethyl is also active. Under suitable conditions, it can be replaced by nucleophiles to form carbon-carbon bonds or carbon-heteroatomic bonds. For example, when reacted with cyanide, a cyanyl group can be introduced, and subsequent hydrolysis steps can be converted into functional groups such as carboxyl groups to expand the structural diversity of the compound.
    Furthermore, the pyridine ring of the compound is aromatic and can undergo electrophilic substitution reaction. Due to the electron-absorbing property of the pyridine nitrogen atom, the electron cloud density on the ring is reduced, the electrophilic substitution reaction activity is lower than that of benzene, and the substituent mainly enters the 3-position of the pyridine ring (relative to the nitrogen atom).
    In addition, 3-bromo-2- (bromomethyl) pyridine may also participate in metal catalytic reactions. Under transition metal catalysis, it can react with metal-containing reagents such as organolithium and organomagnesium reagents to realize the construction of complex organic molecules, which has potential application value in drug synthesis, materials science and other fields.
    Its chemical properties are rich and diverse, and it is an important intermediate in the field of organic synthesis, providing many possible paths for the creation of novel organic compounds.
    What are the precautions for 3-bromo-2- (bromomethyl) pyridine in storage and transportation?
    3 - bromo - 2 - (bromomethyl) pyridine, that is, 3 - bromo - 2 - (bromomethyl) pyridine, there are many things to pay attention to when storing and transporting this substance.
    Let's talk about storage first, this is the key thing. Because it has certain chemical activity, it must be stored in a cool, dry and well-ventilated place. If placed in a high temperature and humid place, it is easy to cause chemical changes and damage its quality. It is advisable to choose a sealed container to prevent contact with air and moisture. Due to the high activity of bromine atoms, it can be deteriorated by water or air components, or by reactions such as hydrolysis and oxidation. And it should be kept away from fire and heat sources. Because it may be flammable, it may be dangerous in case of open flames and hot topics.
    In addition to transportation, it should not be underestimated. When transporting, it should be properly packaged in accordance with relevant regulations. The packaging materials used should be able to prevent leakage and collision, and ensure that there is no risk of material leakage during transportation. During the handling process, the operator should handle it with care, and must not load and unload it brutally to avoid packaging damage. Transportation vehicles should also meet safety standards and be equipped with corresponding fire and emergency treatment equipment, just in case. At the same time, the transportation route planning should also be careful to avoid densely populated areas and environmentally sensitive areas, so as to reduce the harm to the public and the environment in the event of an accident.
    In conclusion, the storage and transportation of 3-bromo-2- (bromomethyl) pyridine must be strictly controlled and operated according to regulations to ensure its safety and quality.