3-Pyridyl Bromide CAS 626-55-1

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3-Pyridyl bromide, more precisely known as 3-Bromopyridine, is a fundamental nitrogen-containing heterocyclic building block in organic synthesis, characterized by a pyridine ring substituted with a bromine atom at the meta position. This specific halogen placement relative to the basic, electron-deficient nitrogen atom creates a distinct electronic environment that dictates its reactivity: the bromine acts as an excellent leaving group, facilitating efficient participation in transition metal-catalyzed cross-coupling reactions (such as Suzuki, Stille, and Negishi couplings) to form carbon-carbon bonds, thereby enabling the versatile introduction of the 3-pyridyl moiety into complex molecular architectures. Simultaneously, the ring nitrogen itself can undergo N-alkylation or serve as a coordinating ligand in metal complexes. The meta relationship between the bromine and nitrogen minimizes direct electronic interference, allowing for relatively orthogonal functionalization. Consequently, 3-bromopyridine is an indispensable intermediate in the pharmaceutical industry for constructing active ingredients (e.g., drugs targeting the central nervous system), in agrochemicals for creating herbicides and insecticides, and in materials science for synthesizing ligands, organic conductors, and coordination polymers. Its utility as a cornerstone for assembling sophisticated nitrogen-rich molecules underscores its significant commercial and research importance.

Preparation of 3-pyridyl bromide:

(1) Take m-aminopyridine as the raw material, dissolve it in hydrobromic acid, slowly add bromine at 0 ℃ and stir it. After the reaction is completed, add sodium nitrite solution, filter it, add sodium hydroxide solution for neutralization, separate out the organic layer, extract it with ether, evaporate the ether, and use vacuum distillation (3.333E3Pa) to obtain the residue.

(2) It is obtained by liquid phase bromination of pyridine under the catalysis of thionyl chloride or aluminum trichloride at low temperature.

Dewatering method:

Newly purchased m-bromopyridine is usually aqueous. If your reaction cannot have water, you need to remove water.

The next day, use the oil pump to decompress and distill. Start to pump air from 10 degrees. There will be a lot of foam in about 10 minutes. Be very careful at this time.

When the foam becomes less, the temperature can be increased. I use 55 degrees Celsius. It took about 4 hours to evaporate 500 ml of m-bromopyridine. Because the distillation temperature is not high, it can be steamed dry safely. The reaction bottle can be washed with water. (Strong potassium oxide will corrode glass over time)

The measured density of m-bromopyridine after such treatment is 1.622. Add sodium metal, no reaction.

Will potassium hydroxide replace the bromine on m-bromopyridine? can't. I heated it at 100 ℃ for one hour, and then did gas phase detection, and there was no change.

There is no relevant literature on the discovery history of 3-pyridyl bromide.

However, pyridine and its derivatives have been studied for nearly two centuries. As early as 1848, the British chemist Anderson isolated pyridine from the liver extract, opening the prelude to the discovery and research of pyridine. At the beginning of the 20th century, people began to deeply explore the structure and properties of pyridine, and gradually discovered various pyridine derivatives, including 3-bromopyridine. At present, 3-bromopyridine has become an important intermediate in the field of organic synthesis and pharmaceutical chemistry, and has been widely used.

Melting point - 27 ° C, Boiling point 173 ° C (lit.), Density 1.64 g/mL at 25 ° C (lit.), Vapor pressure 1.64hPa at 25 ℃, Refractive index n20/D 1.571 (lit.), Flash point 125 ° F, Storage condition Keep in dark place, Inert atmosphere, 2-8 ° C, Solubility 31g/l, Acidity coefficient (pKa) 2.84 (at 25 ℃), Form Liquid, Specific gravity 1.617, Clear colors to yellow or slightly brown, Soluble in water (31 g/L at 20 ° C), BRN 105880, InChIKeyNYPYPOZNGOXYSU-UHFFFAOYSA-N, LogP1.694

3-Pyridyl bromide is an organic compound with multiple uses. The following is a detailed description of the various uses of 3-bromopyridine:

1. Synthetic intermediates
3-Bromopyridine is an important synthetic intermediate mainly used in the synthesis of drugs, alkaloids, and other compounds. Due to its good reactivity and selectivity, 3-bromopyridine plays a crucial role in organic synthesis. By reacting with different chemicals, 3-bromopyridine can be used to prepare various drugs with specific structures and functions. These drugs include anti-tumor drugs, antibiotics, sedatives, antidepressants, etc. In addition, 3-bromopyridine can also be used to synthesize some alkaloids, such as quinoline and isoquinoline.
2. Pesticide synthesis
3-Bromopyridine is also widely used in pesticide synthesis. It can be used to prepare various insecticides, herbicides, and fungicides. By reacting with different pesticide raw materials, 3-bromopyridine can improve the insecticidal effect and durability of pesticides. These pesticides can be used for agricultural production and plant protection, effectively preventing the invasion of pests and pathogens.

3. Flavor synthesis
3-Bromopyridine also has certain applications in the synthesis of spices. It can be used to synthesize a variety of coumarins, which have fragrant fragrance and are widely used in perfume, cosmetics, food additives and other fields. By reacting with other flavoring materials, 3-bromopyridine can prepare various flavoring compounds with unique fragrances and properties.
4. Material preparation
3-Bromopyridine can be used to prepare various polymer materials and composite materials. By polymerizing with other monomers or combining with inorganic materials, 3-bromopyridine can improve the performance and functionality of the material. For example, it can be used to prepare photosensitive resins, electronic coatings, and printed circuit boards. These materials have extensive applications in fields such as electronic equipment, optical devices, and aerospace.

5. Fuel additive
3-Bromopyridine can be used as a fuel additive to improve fuel combustion performance and reduce pollutant emissions. It can serve as a combustion aid or catalyst to promote complete combustion of fuel while reducing the content of pollutants in exhaust gas. These fuel additives can be applied in fields such as aerospace, automobiles, and internal combustion engines to improve fuel combustion efficiency and reduce environmental pollution.
6. Electronic Chemicals
3-Bromopyridine also has certain applications in the field of electronic chemicals. It can be used to prepare photoresists, photosensitive resins, electronic coatings, printed circuit boards, and electronic packaging materials. These materials play a crucial role in the manufacturing of electronic devices, which can improve their performance and reliability. By coordinating or reacting with other electronic chemicals, 3-bromopyridine can improve the electron transfer performance and stability of the material.

7. Biomedical

3-Bromopyridine also has certain applications in the field of biomedicine. It can be used to synthesize biologically active compounds, such as antibiotics, anti-tumor drugs, and alkaloids. These drugs can be used to treat various diseases by binding to different biological molecules or acting on specific cellular targets. In addition, 3-bromopyridine can also be used to study chemical reaction mechanisms and material properties. The application in the field of biomedicine helps to develop more effective drugs and treatment plans, making contributions to human health.
8. Research field
3-Bromopyridine also has certain applications in scientific research. It can be used as a model compound in organic synthesis and drug development, helping scientists understand the synthesis and properties of related compounds. By studying the structure and reaction performance of 3-bromopyridine, it is possible to further explore the synthesis methods and reaction mechanisms of organic compounds. In addition, 3-bromopyridine can also be used to study chemical reaction mechanisms and material properties. The application in the field of scientific research helps to promote the development and progress of fields such as organic chemistry and pharmaceutical chemistry.

1. Toxicity analysis

2.Environmental impact

3.Safety measures and emergency response

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