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What Is 2-Acetylthiophene
2-Acetylthiophene is an organic compound with the chemical formula C7H6OS. It is a yellow liquid and is used as a flavor and fragrance compound due to its sweet, nutty odor. It is also used as a precursor in the synthesis of pharmaceuticals and other organic compounds. The compound is derived from thiophene, a five-membered heterocyclic ring comprised of four carbon atoms and one sulfur atom. The acetyl group is attached to the thiophene ring at the 2-position, resulting in 2-acetylthiophene.
Advantages Of 2-Acetylthiophene
1. Pleasant odor: 2-Acetylthiophene is commonly used in the fragrance industry due to its pleasant, sweet, and fruity odor.
2. Flavor enhancer: This compound is also used as a flavor enhancer in the food industry, specifically in sweet and savory applications.
3. Organic synthesis: 2-Acetylthiophene is a versatile compound that can be used as a starting material in various organic synthesis reactions, including the synthesis of pharmaceuticals and agrochemicals.
4. Electrochemical properties: This compound has been shown to have unique electrochemical properties, making it useful in electrocatalysis and electrochemical sensing.
5. Biological activity: 2-Acetylthiophene has been reported to have some biological activity, including antioxidant and anti-inflammatory effects, which may have potential therapeutic applications.
Application Of 2-Acetylthiophene
1. Flavor and Fragrance industry
2-Acetylthiophene is widely used in the flavor and fragrance industry as a flavor ingredient. It is known for its roasted and nutty aroma, and used in the production of various food flavors, such as coffee, nuts, and popcorn.
Pharmaceutical industry
2-Acetylthiophene is an important intermediate for the synthesis of several pharmaceuticals such as the analgesic drug; spiroxatrine, which is used for the treatment of hypertension and heart diseases.
Agrochemicals industry
It is also used in the agrochemicals industry as a starting material for the synthesis of insecticides, fungicides, and herbicides such as clethodim and pyrazosulfuron-ethyl.
Research and development
2-Acetylthiophene is used extensively in research and development activities as a reagent in the organic synthesis.
1. Thiophene Ring: It is a heterocyclic aromatic compound containing a five-membered ring with four carbon atoms and one sulfur atom.
2. Acetyl Group: It is a functional group consisting of a carbonyl group (C=O) attached to a methyl group (-CH3).
3. Sulfur atom: It is an element that is present in the thiophene ring and forms a part of the ring structure.
Production Methods Of 2-Acetylthiophene
1. Friedel-Crafts Acylation: This is the most common method used for the production of 2-Acetylthiophene. In this process, thiophene is acylated using acetyl chloride in the presence of a Lewis acid catalyst, such as aluminum chloride. The product obtained is then purified by distillation or column chromatography.
2. Thionation: In this method, thiophene is first thionated to form 2-thiothiophene using hydrogen sulfide gas and a catalyst such as iron (III) chloride. The 2-thiothiophene is then oxidized to 2-Acetylthiophene using a strong oxidizing agent, such as hydrogen peroxide or nitric acid.
3. Oxidative Cleavage: In this method, 2-Methylthiophene is oxidatively cleaved using potassium permanganate or hydrogen peroxide in the presence of a catalyst such as iron (III) chloride. The resulting product is 2-Acetylthiophene.
4. Pd-Catalyzed Cross Coupling: In this method, 2-Acetylthiophene is produced by cross-coupling of acetyl chloride and thiophene using a palladium catalyst. The reaction is carried out in the presence of a base and an organic solvent such as tetrahydrofuran or dimethylformamide.
5. Photochemical Reactions: In this method, 2-Acetylthiophene is produced using a photochemical reaction between thiophene and acetyl chloride in the presence of a photosensitizer. The reaction is carried out under UV light in an organic solvent such as benzene or dichloromethane.
What Are The Working Theory Of 2-Acetylthiophene
2-acetylthiophene is an organic compound containing a five-membered ring of four carbon atoms and one sulfur atom.
It is a highly reactive compound due to the presence of an electron-rich sulfur atom and a carbonyl group (C=O) in the molecule.
The thiophene ring in 2-acetylthiophene undergoes substitution reactions with different electrophiles such as halogens, nitro groups, etc.
The carbonyl group in 2-acetylthiophene is a crucial part of the molecule, which plays a significant role in its reactivity.
The carbonyl group undergoes nucleophilic addition reactions with different nucleophiles such as amines, hydrazines, etc.
2-acetylthiophene can be used as a precursor in the synthesis of various drug molecules, agrochemicals, and flavorings.
The presence of a polar sulfur atom and a non-polar benzene ring in the molecule gives 2-acetylthiophene an amphipathic nature.
Process Of 2-Acetylthiophene
01
Synthesis of Thiophene
Thiophene is synthesized by the reaction of sulfur and acetylene in the presence of a catalyst such as iron.
02
Acetylation
Acetic anhydride is added to the thiophene to acetylate it, forming 2-acetylthiophene.
03
Purification
The crude product is purified by distillation or column chromatography.
04
Characterization
The product is characterized by analyzing its physical and chemical properties, such as melting point, boiling point, infrared spectroscopy, and nuclear magnetic resonance spectroscopy.
How To Maintain 2-Acetylthiophene
Storage
Store 2-acetylthiophene in a tightly sealed container, away from heat and light. Store at room temperature or in a refrigerator if possible.
Handling
Wear appropriate personal protective equipment (PPE) such as gloves, safety glasses, and lab coat when handling 2-acetylthiophene. Do not inhale the substance or allow it to come into contact with the skin or eyes.
Use within expiry period
Use 2-acetylthiophene within the expiry period mentioned on the container to ensure its effectiveness and safety.
Labeling
Label the container with the date of receipt, expiry date, and any relevant safety information.
Proper disposal
Dispose of 2-acetylthiophene as per the guidelines provided by local regulations.
Quality control
Regularly check the quality of 2-acetylthiophene using appropriate analytical methods such as HPLC to ensure its purity and efficacy.
Handling in a fume hood
Handle 2-acetylthiophene in a fume hood to prevent any potential inhalation or skin exposure hazards.
Keep away from incompatible substances
2-acetylthiophene should be kept away from incompatible chemicals such as oxidizing agents, acids, and strong bases to prevent any chemical reactions.
1. Chemical suppliers - 2-Acetylthiophene can be purchased from various chemical suppliers.
2. Pharmaceutical companies - Some pharmaceutical companies may produce 2-Acetylthiophene as an intermediate or starting material for the synthesis of other compounds.
3. Research institutions - Research institutions may synthesize 2-Acetylthiophene for use in experiments or to develop new methods of synthesis.
4. Industrial chemical manufacturers - Industrial chemical manufacturers may produce 2-Acetylthiophene for use in various applications, such as in the fragrance and flavor industry.
5. Online marketplaces - 2-Acetylthiophene can also be purchased from various online marketplaces. However, buyers should exercise caution when purchasing chemicals from these sources and ensure they are purchasing from reputable suppliers.
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