5-(Ethylthio)-1H-Tetrazole CAS 89797-68-2

5-(Ethylthio)-1H-tetrazole, molecular formula C3H6N4S. White crystalline solid, soluble in ethanol, dimethyl ether, benzene and acetone, insoluble in water. Pharmaceutical and pesticide intermediates, protective agents for RNA active agents and DNA synthesis active genes.

5-(Ethylthio)-1H-tetrazole has many uses, including the following:

1. As a high energy density compound, it can be used to make energetic materials, such as rocket fuel, pyrotechnics, etc.

2. Due to its remarkable affinity with silver ions, it can be used to prepare silver-containing materials, such as silver wire and conductive glue.

3. As a potential anticancer and antiviral drug, it has the ability to inhibit tumor cells and virus infection, and has been widely used in related medical research.

4. As a metal corrosion inhibitor, it can be used to protect metal surfaces from corrosion.

5. As a catalyst, it can be used to promote organic synthesis reactions, such as oxidation reactions and hydrogenation reactions.

6. As a fluorescent probe, it can be used to detect biological macromolecules, such as proteins and DNA.

The following are three synthetic routes of 5-(Ethylthio)-1H-tetrazole:

1. Imidoyl Chloride method (Imidoyl Chloride method):

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.

2. Ammonium sulfate method (Ammonium sulfate method):

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.

3. Barbituric Acid method:

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:

1. Thermal stability: it is unstable at high temperature and easy to decompose, so it needs to be stored in a dry and cool place.

2. Combustibility: it is a flammable solid, which will emit toxic gas when it burns under open flame or high temperature.

3. Oxidation property: it can be oxidized to its corresponding N-oxide by oxidizing agents.

4. Reducibility: it can be reduced to its corresponding imine by a reducing agent.

5. Reactivity: it can react with oxidizing agents, reducing agents, acids, bases, etc. to generate different compounds.

6. 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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