Tetrabutylammonium Nitrate typically exists in the form of white to off white powder or crystals. This substance is stable at room temperature, not easily decomposed, and has no obvious odor. Molecular formula C16H36N2O3, CAS 1941-27-1. The solubility varies in different solvents. For example, in chloroform, it can dissolve to form a colorless and transparent solution with a high solubility (25mg/ml). In acetonitrile, its solubility is relatively low (0.1g/mL), but it can still form a colorless and transparent solution.
The solubility in water is relatively low, less than 2g/100mL. These solubility data are of great significance for selecting suitable solvents for chemical reactions, extraction, and purification operations. It is a quaternary ammonium salt commonly used in scientific research and inorganic chemical product production. It is commonly used in scientific research for the synthesis of transition metal complexes and can also be used as metal complexes to stabilize metal ions. In addition, tetra-n-butylammonium nitrate can also be used as a phase transfer catalyst for two-phase reactions.
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Chemical Formula |
C16H36N2O3 |
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Exact Mass |
304 |
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Molecular Weight |
304 |
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m/z |
304 (100.0%), 305 (17.3%), 306 (1.4%) |
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Elemental Analysis |
C, 63.12; H, 11.92; N, 9.20; O, 15.76 |
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As a reaction medium and catalyst
Tetra-n-butylammonium nitrate is often used as a reaction medium and catalyst in pharmaceutical synthesis, which can significantly improve reaction rate and yield. The structure of its quaternary ammonium salt endows it with excellent ion exchange ability and phase transfer catalytic performance, thereby effectively promoting the progress of the reaction.
For example, in the synthesis of certain nitrogen-containing heterocyclic compounds with biological activity, Tetra-n-butylammonium nitrate can serve as a phase transfer catalyst to promote the transfer and reaction of reactants between the two phases. By adjusting the reaction conditions and catalyst dosage, precise control of product structure and yield can be achieved.
Participate in the introduction of specific functional groups
Tetra-n-butylammonium nitrate can also participate in the introduction of specific functional groups in pharmaceutical synthesis. The nitrate ions in its structure have strong oxidizing properties and can react with certain functional groups, thereby introducing new functional groups or changing the properties of existing functional groups.
For example, in the synthesis of certain drugs with anti-tumor activity, the hydroxyl group in the drug molecule can be oxidized to aldehyde or carboxyl groups through the oxidation of Tetra-n-butylammonium nitrate, thereby increasing the activity and stability of the drug.
Application of Ionic Liquids in Drug Extraction
Ionic liquids are salt compounds that remain liquid at room temperature, characterized by low volatility, high thermal stability, and good solubility. Tetra-n-butylammonium nitrate, as a quaternary ammonium salt ionic liquid, has broad application prospects in drug extraction.
By adjusting the structure and composition of ionic liquids, selective extraction and separation of different drug molecules can be achieved. This method has the advantages of easy operation, high efficiency, and low environmental pollution, and has broad application prospects in the pharmaceutical industry.
Efficiency leap Precision and stability
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Specific application examples of tetrabutylammonium nitrate in pharmaceutical synthesis
Synthesis of 2,6-dichloropurine nucleoside
2,6-dichloropurine nucleoside is a drug with anti-tumor activity, and its synthesis process requires the introduction of nitro functional groups. Tetra-n-butylammonium nitrate played a crucial role in the synthesis process.
The specific steps are as follows: Firstly, using inexpensive inosine as the raw material, 2 ', 3', 5 '- tri-O-acetyl-6-chloropurine nucleoside is obtained through acetylation of the sugar group and chlorination reaction of the purine base 6-carbonyl group. Then, using dichloromethane as the solvent, a nitro group was introduced at the 2-position of purine in the presence of trifluoroacetic anhydride and Tetra-n-butylammonium nitrate. Finally, the two-step reaction of removing acetyl and nitrochlorination was completed in HCl/EtOH solution, resulting in 2,6-dichloropurine nucleoside with a purity of up to 98% (HPLC) and a total yield of 63%.
In this synthesis process, Tetra-n-butylammonium nitrate not only introduced nitro functional groups as a nitration reagent, but also promoted the progress of the reaction and the purification of the product.
Synthesis of 6-Chloro-2-Nitro-9-Pyranopurine
6-Chloro-2-nitro-9-pyranopurine is an important pharmaceutical intermediate that plays a crucial role in the synthesis of antiviral drugs. Tetra-n-butylammonium nitrate also played a crucial role in the synthesis process.
The specific steps are as follows: Firstly, using inexpensive 6-chloropurine as raw material, protect the 9-position NH of 6-chloropurine with tetrahydropyranyl group. Then, using dichloromethane as the solvent, 6-chloro-2-nitro-9-pyranopurine was obtained with an 85% yield in the presence of trifluoroacetic anhydride and Tetra-n-butylammonium nitrate system.
In this synthesis process, Tetra-n-butylammonium nitrate acts as a nitration reagent and catalyst, promoting the introduction of nitro functional groups and the progress of the reaction. Meanwhile, by adjusting the reaction conditions and catalyst dosage, precise control over the product structure and yield can be achieved.
Synthesis of 2-Fluoroadenine
2-Fluoroadenine is a drug with antiviral and anti-tumor activity, and its synthesis process is relatively complex. Tetra-n-butylammonium nitrate also played an important role in the synthesis process.
The specific steps are as follows: Firstly, 6-chloropurine is used as the raw material, and after protection, nitration, fluorination, and ammonolysis, 2-fluoroadenine is obtained. Among them, in the nitration step, Tetra-n-butylammonium nitrate acts as a nitration reagent and catalyst, promoting the introduction of nitro functional groups and the progress of the reaction.
Through this synthesis process, high-purity 2-fluoroadenine can be obtained, providing important raw materials for subsequent drug development and research.
Synthesis of other nitrogen-containing heterocyclic compounds
In addition to the specific application examples mentioned above, Tetra-n-butylammonium nitrate can also be used to synthesize other nitrogen-containing heterocyclic compounds with biological activity. These compounds have broad application prospects in the pharmaceutical field, such as anti-tumor drugs, antiviral drugs, neuromodulatory drugs, etc.
During the synthesis of these compounds, Tetra-n-butylammonium nitrate can serve as a phase transfer catalyst or nitration reagent to facilitate the reaction and purification of the product. By adjusting the reaction conditions and catalyst dosage, precise control of product structure and yield can be achieved, thereby meeting the requirements of drug synthesis.
monium nitrate, TBAN, as an important quaternary ammonium salt compound, has unique applications and significant advantages in the field of fireworks manufacturing. Its excellent chemical and physical properties make tetrabutylammonium nitrate an indispensable key raw material in the fireworks manufacturing process. The following is a detailed discussion on the specific uses of Tetra-n-butylammonium nitrate in fireworks manufacturing.
Application principle of tetra-n-butylammonium nitrate in fireworks manufacturing
During the fireworks manufacturing process, Tetra-n-butylammonium nitrate mainly plays the following roles:
Provide oxidant:
The nitrate ion (NO3-) in tetra-n-butylammonium nitrate has strong oxidizing properties and can be used as an oxidant in pyrotechnic agents. In fireworks reactions, oxidants and reducing agents undergo redox reactions, releasing a large amount of heat and light energy, resulting in colorful fireworks effects.
Improving combustion performance:
The addition of tetra-n-butylammonium nitrate can improve the combustion performance of pyrotechnic agents, making their combustion more complete and uniform. This helps to increase the brightness and duration of fireworks, making the fireworks effect more spectacular.
Adjusting the color of fireworks:
By adjusting the ratio and type of tetra-n-butylammonium nitrate to other fireworks, precise control of the color of fireworks can be achieved. When different metal ions and organic compounds react with Tetra-n-butylammonium nitrate, they produce flames and fireworks of different colors.
Specific application of Tetra-n-butylammonium nitrate in fireworks manufacturing
Colorful fireworks manufacturing
In the production of colored fireworks, Tetra-n-butylammonium nitrate is used as one of the oxidants and mixed with metal salts (such as copper salts, strontium salts, barium salts, etc.) and organic fuels to make fireworks. When fireworks are ignited, Tetra-n-butylammonium nitrate provides an oxidant, which undergoes redox reactions with metal ions and organic fuels, releasing a large amount of heat and light energy. These energies are manifested in the form of light radiation, creating colorful fireworks effects.
By adjusting the ratio of Tetra-n-butylammonium nitrate to metal salts and organic fuels, precise control of the color of fireworks can be achieved. For example, increasing the proportion of copper salts can make fireworks appear blue or green; Increasing the proportion of strontium salts can make fireworks appear red or orange. In addition, Tetra-n-butylammonium nitrate can also be mixed with other oxidants such as perchlorates, nitrates, etc. to further enhance the brightness and duration of fireworks.
Smoke and Fireworks Manufacturing
In smoke and fireworks manufacturing, tetrabutylammonium nitrate is also used as one of the oxidants, but mixed with compounds that produce smoke (such as sulfur, carbon, etc.) to make fireworks. When the fireworks are ignited, Tetra-n-butylammonium nitrate provides an oxidant, which undergoes redox reactions with compounds that produce smoke, generating a large number of tiny particles. These particles suspend in the air and scatter light, creating a smoke effect.
By adjusting the ratio and type of Tetra-n-butylammonium nitrate to compounds that produce smoke, precise control of smoke density and color can be achieved. For example, increasing the proportion of sulfur can make smoke appear yellow or brown; Increasing the proportion of carbon can make the smoke appear black or gray. In addition, Tetra-n-butylammonium nitrate can also be mixed with other additives (such as adhesives, combustion aids, etc.) to further improve the stability and persistence of smoke.
Flash fireworks manufacturing
Flash fireworks are fireworks products that produce strong light in a short period of time. In the production of sparkling fireworks, Tetra-n-butylammonium nitrate is used as one of the oxidants and mixed with reducing agents such as aluminum powder or magnesium powder to make fireworks. When the fireworks are ignited, Tetra-n-butylammonium nitrate provides an oxidant and undergoes a violent oxidation-reduction reaction with metal aluminum or magnesium powder, releasing a large amount of heat and light energy. These energies are manifested in the form of light radiation, forming a strong flashing effect.
The brightness and duration of flash fireworks depend on the ratio and type of Tetra-n-butylammonium nitrate to metallic aluminum or magnesium powder. By adjusting these parameters, precise control of the flashing effect can be achieved. In addition, Tetra-n-butylammonium nitrate can also be mixed with other additives (such as adhesives, combustion aids, etc.) to improve the stability and reliability of flash fireworks.
Special effects fireworks manufacturing
In addition to colored fireworks, smoke fireworks, and sparkling fireworks, Tetra-n-butylammonium nitrate can also be used to manufacture other special effects fireworks products. For example, in the production of explosive fireworks, Tetra-n-butylammonium nitrate can be used as a part of the explosive agent and mixed with other explosive agents to make fireworks. When fireworks are ignited, a violent explosive reaction occurs, producing a huge sound and shock wave.
In addition, Tetra-n-butylammonium nitrate can also be used to manufacture fireworks products with special effects such as rotating fireworks and flamethrowers. In these pyrotechnic products, tetrabutylammonium nitrate is used as one of the oxidants and mixed with other pyrotechnic agents to form the agent layer or fuel layer. When fireworks are ignited, the propellant layer or fuel layer undergoes a combustion reaction, producing a specific fireworks effect.
Early Exploration and Synthetic Background (1940s–1950s)
The discovery of tetrabutylammonium nitrate (CAS: 1941-27-1) is closely associated with the research wave of quaternary ammonium compounds. In the 1940s, the organic chemistry community carried out systematic investigations into the structure and properties of quaternary ammonium cations. The tetrabutylammonium cation became a research focus due to its excellent liposolubility and stability. The compound was first synthesized and registered with a CAS number in 1941, prepared via the metathesis reaction between tetrabutylammonium halide and nitrate. Early synthesis mainly relied on the room-temperature aqueous reaction of tetrabutylammonium chloride and sodium nitrate, where the target product could be obtained through simple stirring. This method laid the foundation for subsequent research. At that time, it was only used as a basic chemical reagent and had not entered the stage of applied research.
Academic Research and Property Characterization (1960s–1970s)
Starting from the 1960s, the physicochemical properties of tetrabutylammonium nitrate were gradually characterized systematically. In 1968, D. J. Turner and R. M. Diamond from the University of California, Berkeley, first studied its extraction behavior, confirming that it could be extracted from the aqueous phase by long-chain alcohols and revealing its ionic solvation characteristics. In 1970, Coker et al. determined its melting point to be 392.2 K (119 °C), identified it as a white crystalline solid, and supplemented the basic physical property data. During the same period, the academic community began to pay attention to its ionic conductivity in non-aqueous systems, foreshadowing its subsequent applications in electrochemistry and phase-transfer catalysis.
Application Expansion and Industrial Development (1980s to Present)
The practical value of tetrabutylammonium nitrate was explored in the 1980s. In 1984, research verified its role as a mild nitrate donor for the nitration of acid-sensitive carbohydrates, demonstrating its unique advantages in organic synthesis. Since then, its applications as a phase-transfer catalyst, ionic liquid precursor, and electrolyte additive have been gradually expanded. With the optimization of synthetic processes, the purity and yield of the metathesis reaction have been greatly improved. The compound has evolved from a laboratory reagent to large-scale production, becoming a commonly used reagent in organic synthesis, electrochemistry, separation science and other fields. Its discovery and development history also serve as a typical case of the transformation of quaternary ammonium compounds from basic research to applied utilization.
FAQ
What is the use of Tetrabutylammonium bromide?
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Tetrabutylammonium bromide (TBABr) is a frequently used chemical in industrial processes and academic research. It serves as phase transfer catalyst, pH regulator, or as supporting electrolyte.
Is tetrabutylammonium bromide soluble in water?
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Tetrabutylammonium bromide, also known as tetrabutylammonium bromide. White crystal, deliquescence. 118 ℃ melting point. Soluble in water, alcohol, ether and acetone, slightly soluble in benzene.
What are the hazards of TBAB?
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Hazard statements : H302 Harmful if swallowed. H315 + H320 Causes skin and eye irritation. H361 Suspected of damaging fertility or the unborn child. H412 Harmful to aquatic life with long lasting effects.
What is the flash point of TBA?
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TBA is a low molecular weight, highly flammable liquid of moderate volatility with a flash point of 15°C (59°F). It freezes/melts around 26°C (79°F) and will either be present as a colorless liquid with a camphor-like odor, or an off-white solid block depending on ambient temperature.
Is tert-butyl a strong base?
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The tert-butoxide is a strong, non-nucleophilic base in organic chemistry. It readily abstracts acidic protons from substrates, but its steric bulk inhibits the group from participating in nucleophilic substitution, such as in a Williamson ether synthesis or an SN2 reaction.
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