5-Bromonicotinonitrile is usually in the form of a white or pale yellow solid powder. The molecular weight is approximately 183.01 g/mol, CAS 35590-37-5, molecular formula C6H3BrN2, and density is approximately 1.72 g/cm ³. Under normal circumstances, it is stable and not easily decomposed. This means that the compound can be stored for a long time in a suitable environment without significant chemical changes. However, prolonged exposure to adverse conditions such as high temperatures or ultraviolet radiation may affect its stability.
It can dissolve in various organic solvents such as ethanol, ether, etc. The relatively low solubility in water indicates that the compound has a weak affinity for water. Due to its active groups such as nitrile and bromine atoms, this compound can participate in various chemical reactions. For example, it can undergo substitution or addition reactions with various nucleophiles, or be converted into other valuable compounds through esterification, reduction, and other reactions.
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Chemical Formula |
C6H3BrN2 |
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Exact Mass |
182 |
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Molecular Weight |
183 |
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m/z |
182 (100.0%), 184 (97.3%), 183 (6.5%), 185 (6.3%) |
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Elemental Analysis |
C, 39.38; H, 1.65; Br, 43.66; N, 15.31 |
Roles in environmental protection
5-Bromonicotinonitrile plays an important role in the field of environmental protection. As a catalyst or reactant, it can be used to convert toxic and harmful substances, significantly reducing their impact on the environment. Specifically, it can participate in various chemical reactions, converting toxic chemicals into harmless or low toxic substances, thereby effectively reducing the harm of these substances to the environment and organisms.
It can be used as a catalyst or reactant to convert toxic and harmful substances and reduce their impact on the environment. For example, it can participate in chemical reactions, converting toxic chemicals into harmless or low toxicity substances, thereby reducing the harm to the environment and organisms.
In wastewater treatment, it can be used as a flocculant or adsorbent to remove harmful substances from wastewater.
It can react with harmful ions or organic substances in wastewater, adsorb or convert them into harmless substances. This not only reduces the content of toxic substances in wastewater, but also meets the requirements of discharge standards or recycling, thereby protecting the safety of water bodies and ecological environment.
3. Soil remediation
It also has potential in soil remediation. It can be used as a soil amendment or chemical fixative to reduce the risk of toxic and harmful substances in soil.
By reacting with harmful substances in the soil, they can be transformed into stable compounds or fixed in the soil, thereby reducing their risk to the environment and ecosystem. This helps to reduce soil pollution, improve soil quality, and promote ecosystem restoration and sustainable development.
It also has the potential for application in air pollution control. It can be used as a catalyst or reactant to convert harmful substances in the atmosphere.
By participating in reactions, harmful gases such as nitrogen oxides and sulfur oxides in the atmosphere can be transformed into harmless or low toxic substances. For example, it can participate in reactions to convert harmful gases such as nitrogen oxides and sulfur oxides in the atmosphere into harmless or low toxicity substances, which helps to reduce the impact of these harmful gases on the environment and human health, and improve air quality.
Roles in Functional Materials
The product is a vital organic building block for the synthesis of high-end heterocyclic functional materials. Its multiple reactive sites formed by the pyridine ring, bromine atom and cyano group endow the compound with excellent capabilities for molecular modification and coordination.
In metal-organic framework (MOF) materials, the pyridine nitrogen atom can coordinate with metal ions such as copper and zinc, and form synergistic bonds together with cyano groups to construct structurally ordered and pore-tunable fluorescent MOFs.
Featuring stable optical properties, such materials are widely applied in environmental monitoring, biological fluorescence sensing and micro light-emitting components, with outstanding detection accuracy and anti-interference performance.In the field of organic optoelectronic materials, the electron-deficient pyridine skeleton can regulate molecular energy levels and improve electron transport efficiency.
Derivatized via coupling, cyclization and other reactions, it can be used to synthesize conjugated organic semiconductors for organic field-effect transistors and organic photovoltaic devices, which effectively boost carrier mobility and photoelectric conversion efficiency.
Furthermore, it serves as a precursor for graft modification of polymer materials, enhancing their heat resistance, chemical stability and optoelectronic properties. It facilitates the research, development and industrial application of flexible electronics and special polymer materials, acting as an important intermediate connecting organic synthesis and high-end functional materials.
There are various laboratory synthesis methods for 5-Bromonicotinonitrile, and the following are two commonly used synthesis methods:
Method 1
HClO + NaBr + C2H5OH → C6H3BrN2 + NaCl + H2O
The above equation represents a substitution reaction between cyanide chloride and sodium bromide in an ethanol solvent, resulting in the formation of 5-Bromonicotininitrile and by-products such as sodium chloride, ethanol, and water.
This reaction is a typical nucleophilic substitution reaction, in which cyanide chloride acts as a nucleophilic reagent to attack the bromine atom in sodium bromide, generating a new carbon nitrogen bond.
Mix cyanide chloride and sodium bromide in a 1:1 ratio in a dry flask, and add an appropriate amount of ethanol as the solvent.
Heat the mixture under stirring to reflux temperature (about 70-80 ° C) and reflux reaction for about 2-3 hours until the mixture becomes clear.
After the reaction is completed, cool the reaction solution to room temperature and filter to remove the generated sodium bromide precipitate.
Add an appropriate amount of ammonia water to the filtrate and adjust the pH value to acidic. At this time, crystals of 5-Bromonicotininitrile will precipitate from the solution.
Filter the crystals and wash with a small amount of ethanol and water to remove excess impurities.
Air dry or dry the crystals to obtain 5-Bromonicotininitrile products.
Method 2
Substitution reaction of sodium cyanide and bromine in ethanol solvent:NaCN + Br2 + C2H5OH → C6H3BrN2 + NaBr + HCN + H2O
This reaction is a typical nucleophilic substitution reaction, in which sodium cyanide acts as a nucleophilic reagent to attack the bromine atom in the bromine molecule, generating a new carbon nitrogen bond. The use of ethanol as a solvent in this reaction helps to promote the progress of the reaction.
Electrolytic melting of magnesium chloride to produce magnesium:MgCl2 (molten) → Mg + Cl2 ↑
In this reaction, magnesium ions are reduced to magnesium metal by electrolyzing molten magnesium chloride. Magnesium chloride undergoes ionization in a molten state, generating magnesium ions and chloride ions. During the electrolysis process, the current passes through the molten magnesium chloride, causing magnesium ions to obtain electrons and reduce to magnesium metal. At the same time, chloride ions lose electrons and generate chlorine gas.
Experimental preparation
Ensure that the laboratory environment is dry, tidy, and well ventilated.
Prepare all necessary raw materials and reagents: sodium cyanide, bromine, sulfuric acid, ethanol, etc.
Ensure that laboratory personnel wear appropriate personal protective equipment, such as chemical protective goggles, lab clothes, chemical protective gloves, etc.
Mixing sodium cyanide and bromine
In a dry flask, add sodium cyanide to an appropriate amount of ethanol and stir until dissolved. The function of ethanol is to act as a solvent to better dissolve sodium cyanide in the reaction system.
Subsequently, slowly add bromine and ensure that bromine is completely dissolved in ethanol. Be careful to add slowly to avoid danger caused by intense reactions.
Heating reflux reaction
Heat the mixture to reflux temperature (approximately 70-80 ° C) and maintain reflux state. Reflux reaction helps to promote the reaction and ensure sufficient mixing of reactants.
The reflux reaction takes about 2-3 hours, during which continuous stirring is required to ensure sufficient contact and mixing of the reactants.
Cooling and filtration
After the reaction is completed, cool the mixture to room temperature. At this point, the 5-Bromonicotininitrile crystal begins to precipitate.
Filter the mixture and separate the generated 5-Bromonicotininitrile crystals and mother liquor. The mother liquor contains unreacted raw materials and other by-products.
Washing and drying
Wash the filtered product crystal alternately with a small amount of ethanol and water to remove impurities and unreacted substances attached to the surface of the crystal.
Air dry or use an oven to dry the crystals at an appropriate temperature to obtain a dry 5-Bromonicotininitrile product.
Post experimental processing
Clean up the experimental site and ensure that all reagents and waste are disposed of in accordance with laboratory regulations. Especially bromine and sodium cyanide are toxic and corrosive substances that must be properly handled.
Record experimental data and results, and conduct necessary analysis.
Across various industries, 5-bromonicotinonitrile boasts considerable development potential owing to the reactive advantages of its difunctional groups. In the pharmaceutical sector, the vigorous research and development of targeted drugs, novel anti-tumor agents and PROTAC molecules continuously drive the market demand for this intermediate. As the pesticide industry shifts toward low-toxicity and high-efficiency products, the commercialization of nicotinamide-based green fungicides and new insecticides further expands its application scale.
In the functional materials industry, the rapid advancement of flexible electronics, intelligent sensors and new optoelectronic materials has opened up new growth opportunities. Meanwhile, the industry keeps optimizing green production processes such as bromination and continuous flow synthesis, which effectively reduces waste discharge and manufacturing costs and promotes large-scale production.
Currently, domestic production capacity is gradually expanding alongside intensified market competition. The industry is expected to evolve toward high-purity refined products, customized synthesis services and high-value-added downstream derivatives in the future. Overall, this compound covers three booming sectors: pharmaceuticals, pesticides and functional materials. Its market demand maintains steady growth, presenting promising industrialization prospects and commercial value in the long run.
The discovery of the product is closely linked to the research on pyridine chemistry and nicotinonitrile derivatives. In the mid-19th century, Scottish chemist Thomas Anderson first isolated pyridine, laying the foundation for pyridine ring chemistry. At the beginning of the 20th century, 3-cyanopyridine (nicotinonitrile) was synthesized and gained attention as a precursor of vitamin B3.
The product was first synthesized and characterized during the systematic research on halogenated pyridine derivatives in the 1960s and 1970s, initially aimed at expanding the library of pharmaceutical and pesticide intermediates. Its early synthetic methods mainly included the bromination of 3-cyanopyridine and the dehydration of 5-bromonicotinamide.
After 2010, synthetic routes were gradually optimized to be greener and more efficient. With the rise of coupling reactions and heterocyclic functional materials, its value as a versatile building block has been continuously explored, and its applications have evolved from laboratory research to industrial production.
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