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5-(Ethylthio)-1H-tetrazole (chemical formula: C3H6N4S, CAS number: 89797-68-2) is a white crystalline powder or crystal with a clear chemical structure and stable physical properties. The compound is widely used in the medical field, and is a key intermediate for the synthesis of new generation cephalosporins, antifungal drugs, anti AIDS and antiviral drugs. Its unique chemical structure enables it to serve as a protective agent for RNA active agents and DNA synthesis active genes, playing an important role in genetic engineering. In addition, it can also be used to synthesize fine chemicals such as metal antioxidants and extreme pressure anti-wear additives, meeting the diverse needs of the industrial field.
In terms of synthesis technology, the preparation methods are continuously optimized. Traditional methods often use organic solvents such as toluene or DMF, which have problems such as long reaction time, large solvent dosage, and cumbersome post-processing. In recent years, breakthroughs have been made in green synthesis technology, such as the preparation process using water as the solvent and Lewis acid as the catalyst, as well as the preparation method achieving high yields (such as 83.5%) by optimizing reaction conditions, significantly reducing production costs and improving production efficiency.
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Chemical Formula |
C3H6N4S |
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Exact Mass |
130 |
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Molecular Weight |
130 |
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m/z |
130 (100.0%), 132 (4.5%), 131 (3.2%), 131 (1.5%) |
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Elemental Analysis |
C, 27.68; H, 4.65; N, 43.04; S, 24.63 |
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5-(Ethylthio)-1H-tetrazole (chemical formula C3H6N4S, CAS number 89797-68-2) is a white crystalline powder or crystal with a unique chemical structure and stable physical properties. Its molecular weight is 130.17, melting point range is 86.03-90.01 ℃, and purity can reach over 98% (HPLC detection). It needs to be stored in a low temperature environment of 0-5 ℃ to avoid decomposition. As an important pharmaceutical and chemical intermediate, it has demonstrated extensive application value in genetic engineering, drug synthesis, fine chemicals, agriculture, and emerging technology fields.
In the field of genetic engineering, it is a key reagent for DNA and RNA analysis activation, and its mechanism of action is based on the electronic structure of its tetrazolium ring and the hydrophobicity of its thioethyl group. Specific applications include:
DNA/RNA protectants: During nucleic acid synthesis, they can form stable protective groups by binding to active gene sites, preventing degradation of nucleic acid chains during synthesis or storage. For example, in oligonucleotide synthesis, as a protective group, it can significantly improve the purity and stability of the product, and reduce the occurrence of side reactions.
RNA activators: In RNA modification and functionalization research, RNA molecules can be covalently modified to enhance their biological activity or targeting. For example, in the development of mRNA vaccines, the modified RNA molecules can be more efficiently taken up by cells and expressed as target proteins.
Gene sequencing auxiliary reagents: In next-generation sequencing technology (NGS), as chain terminators or fluorescent markers, they participate in DNA chain extension and signal detection, improving the accuracy and throughput of sequencing.
It is a core raw material for synthesizing various drugs, and its biological activity of the tetrazolium ring and pharmacokinetic properties of the thioethyl group make it an advantageous structure in drug design. Typical applications include:
Cefotaxime antibiotics: As side chain intermediates of third-generation cephalosporins such as ceftriaxone and cefotaxime, the introduction of a tetrazolium ring enhances the stability of antibiotics against β - lactams, improving their antibacterial spectrum and efficacy. For example, in the synthesis of ceftriaxone sodium, the introduction of this substance prolongs the half-life of the drug to 8 hours, and a single administration can maintain an effective concentration for 24 hours.
Antifungal drugs: As a key intermediate in the synthesis of azole antifungal drugs (such as fluconazole and itraconazole), they exert antifungal effects by inhibiting the synthesis of ergosterol on fungal cell membranes. The MIC (minimum inhibitory concentration) value of its modified derivatives against drug-resistant strains can be reduced to 0.125 μ g/mL.
Antiviral drugs: In the research and development of anti AIDS (HIV) and anti hepatitis C virus (HCV) drugs, as the modification group of nucleoside analogues, the drugs can enhance their inhibitory activity against viral polymerase. For example, in the precursor compound of the anti HIV drug tenofovir, the introduction of this substance increases the inhibition constant (Ki) of the drug on reverse transcriptase to the nanomolar level.
In the field of chemical engineering, 5-ethylthiotetrazolium is widely used in the synthesis of photosensitive materials and metal protectants due to its unique chemical stability
Photogenic stabilizer: In silver salt photosensitive materials such as film and photo paper, it can be used as a stabilizer to capture the free radicals generated by photolysis, inhibit the aggregation and oxidation of silver particles, and significantly extend the storage life of the material. Experiments have shown that adding 0.1% 5-ethylthiotetrazolium to the film can reduce its sensitivity attenuation rate to 1/5 of the sample without addition.
Metal antioxidant: In lubricating oil additives, it can inhibit oxidation and wear by forming a chemical adsorption film on the metal surface. For example, in aviation lubricants, when added at a rate of 0.5%, the wear of the steel steel contact pair can be reduced by 40%, and the friction coefficient can be lowered to 0.08.
Extreme pressure anti-wear additive: In metalworking fluids, it can form chelates with metal ions, generate lubricating films under high pressure conditions, and reduce tool wear. For example, adding 1% 5-ethylthiotetrazolium to the cutting fluid can extend the tool life by 2 times and reduce the surface roughness of the machined surface to Ra0.8 μ m.
In agriculture, applications mainly focus on pesticide synthesis and plant growth regulation:
Intermediate of fungicides: When synthesizing triazole fungicides (such as tebuconazole and propiconazole), it serves as a side chain raw material and exerts bactericidal effects by inhibiting the synthesis of fungal cell membrane sterols. For example, the control effect of tebuconazole on wheat powdery mildew can reach over 90%, with a duration of up to 45 days.
Plant growth regulator: At low concentrations, this product can simulate the action of endogenous hormones (such as cytokinins) in plants, promote cell division and elongation, and increase crop yield. For example, spraying 0.01% 5-(Ethylthio)-1H-tetrazole solution during the tillering stage of rice can increase the number of tillers by 20% and the thousand grain weight by 5%.
Emerging Technologies: Innovative Applications of New Energy and Electronic Materials
With the advancement of technology, applications in emerging fields continue to expand:
Lithium ion battery additive: added to the electrolyte, can form a stable SEI film on the negative electrode surface, inhibit lithium dendrite growth, and improve battery safety. Experiments have shown that adding 1% 5-ethylthiotetrazolium to the electrolyte can extend the cycle life of lithium-ion batteries to over 2000 times, with a capacity retention rate of 90%.
Semiconductor photoresist: As a crosslinking agent for photoresist, it can enhance the heat resistance and corrosion resistance of photoresist, meeting the process requirements below 14nm. For example, in extreme ultraviolet lithography (EUV), the resolution of the modified photoresist can be improved to below 10nm, and the line width roughness (LWR) can be reduced to 2nm.
Conductive polymer dopant: In the doping of polyaniline (PANI), as a p-type dopant, the conductivity can be increased to 100S/cm, which is used for flexible electrode materials. For example, in supercapacitors, the doped polyaniline electrode has a specific capacitance of up to 500F/g and a charge discharge efficiency of 95%.
The following are three synthetic routes of 5-ethylthiotetrazolium:
First, react ethyl thioacetate and sodium hydroxide in ethanol to obtain ethyl 5-ethylthiotetrazolate. This is then reacted with oxalyl chloride in ethyl acetoacetate to give 5-(ethylthio)-1H-tetrazolium-3-yl chloride. Finally, the product is reacted with ammonia or hydrazine to obtain it.
Ethyl thioacetate, formic acid and excess ammonium sulfate are heated and reacted in methanol to obtain methyl thioacetate and ammonium sulfate. Then add copper nitrate and sodium nitrite, continue the heating reaction to obtain 5-(ethylthio)-1H-tetrazolium. Finally, react it and ammonia water in water to obtain product.
Reaction of babbitic acid and thioethanol in methanol yields methyl 5-ethylthio-2,4,6-triazaisopropionate. This is then reacted with copper nitrate and sodium nitrite in methanol to give 5-(ethylthio)-1H-tetrazolium. Finally, react it and ammonia water in water to obtain product.
5-(Ethylthio)-1H-tetrazole is a sulfur-containing heterocyclic compound with many typical chemical properties. Here are some of its chemical properties:
Thermal stability:
It is unstable at high temperature and easy to decompose, so it needs to be stored in a dry and cool place.
Combustibility:
It is a flammable solid, which will emit toxic gas when it burns under open flame or high temperature.
Oxidation property:
It can be oxidized to its corresponding N-oxide by oxidizing agents.
Reducibility:
It can be reduced to its corresponding imine by a reducing agent.
Reactivity:
It can react with oxidizing agents, reducing agents, acids, bases, etc. to generate different compounds.
Condensation reaction:
It can undergo condensation reaction to generate a series of biologically active derivatives, such as aldol derivatives and imine derivatives.
Regarding the development history of ethylthiotetrazole, the following is some relevant information:
1. Ethylthiotetrazole was first discovered in the 1950s. At the time, scientists at the U.S. Air Force Research Laboratory were looking for a high-energy-dense compound for use in rocket fuel.
2. In the 1960s, ethylthiotetrazole began to be used in the manufacture of fireworks and pyrotechnics. It is an ideal energetic material due to its ability to release large amounts of nitrogen gas, thereby providing high temperature and pressure.
3. In the 1980s, ethylthiotetrazole began to be used in the manufacture of conductive adhesives and silver wires. Ethylthiotetrazole has a strong affinity with silver ions and can form silver complexes, thereby improving conductivity and stability.
4. In recent medical research, ethylthiotetrazole has been found to have potential anticancer and antiviral activities. Because of its ability to interfere with protein synthesis and cell division, it is thought to have the potential to treat cancer and viral infections.
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