100421-52-1 | 2-Thiophenecarboxylicacid,3-fluoro-,methylester(9CI)

CAS:100421-52-1 | 2-Thiophenecarboxylicacid,3-fluoro-,methylester(9CI),Description

Methyl 3-fluorothiophene-2-carboxylate is a chemical compound with the molecular formula C6H5FO2S. It is a solid substance that should be stored in a dark place, under an inert atmosphere, and at a temperature between 2-8°C.

Synthesis Analysis

The synthesis of Methyl 3-fluorothiophene-2-carboxylate involves several steps. One method involves heating a mixture of 2-(methoxycarbonyl)thiophene-3-diazonium hexafluorophosphate and sand at 250°C under vacuum. The product is then collected using ether, washed with aqueous saturated NaHCO3, and dried over Na2SO4. Another method involves the reaction of the compound with lithium aluminium hydride in tetrahydrofuran at 0°C.

Molecular Structure Analysis

The InChI code for Methyl 3-fluorothiophene-2-carboxylate is 1S/C6H6FO2S/c1-9-6(8)5-4(7)2-3-10-5/h2-3H,1H3. This indicates that the molecule consists of six carbon atoms, six hydrogen atoms, one fluorine atom, two oxygen atoms, and one sulfur atom.

Chemical Reactions Analysis

Methyl 3-fluorothiophene-2-carboxylate can undergo several chemical reactions. For instance, it can react with lithium aluminium hydride in tetrahydrofuran at 0°C to form (3-Fluoro-2-thienyl)methanol. It can also be converted to 3-fluorothiophene-2-carboxylic acid by stirring a solution of 3-fluorothiophene-2-carboxylic acid in methanol with H2SO4 at 100°C.

Physical And Chemical Properties Analysis

Methyl 3-fluorothiophene-2-carboxylate has a molecular weight of 160.17. It has a high gastrointestinal absorption and is permeable to the blood-brain barrier. It is soluble in water, with a solubility of 1.57 mg/ml.

Scientific Research Applications

Synthesis of Fluorothiophenes

Methyl 3-fluorothiophene-2-carboxylate is utilized in the synthesis of 3-fluorothiophenes, offering a new, efficient route. The fluorine atom is introduced into the thiophene ring using the Schiemann reaction, followed by saponification and decarboxylation to yield 3-fluorothiophene with high efficiency (Pomerantz & Turkman, 2008).

Intermediate in Aminofluorothiophene Synthesis

It is a key intermediate in the attempted synthesis of 2-amino-3-fluorothiophene. Special conditions for the Schiemann reaction are required for its preparation, indicating its significance in complex synthetic pathways (Kobarfard, Kauffman, & Boyko, 1999).

Synthesis of Substituted α-Carboxy-γ-Fluorothiophenes

A novel method for synthesizing substituted α-carboxy-γ-fluorothiophenes involves the reaction between methyl thioglycolate anion and α-fluoro-β-(phenylthio)enones, demonstrating the chemical versatility of methyl 3-fluorothiophene-2-carboxylate (Andrès, Laurent, & Marquet, 1997) .

Copper-Mediated N-Arylation

The compound is used in copper-mediated N-arylation processes, showcasing its role in developing new synthesis protocols for complex molecules. This process highlights its importance in creating diverse chemical structures (Rizwan et al., 2015).

Crystal Structure and Computational Study

Methyl 3-fluorothiophene-2-carboxylate's crystal structure and properties have been extensively studied, indicating its significance in the understanding of molecular interactions and structural chemistry (Tao et al., 2020).

Scientific Research Applications of Methyl 3-Fluorothiophene-2-Carboxylate

Synthesis of Fluorothiophenes

Methyl 3-fluorothiophene-2-carboxylate plays a crucial role in the synthesis of 3-fluorothiophenes. It serves as a key intermediate, where the fluorine atom is introduced into the thiophene ring using the Schiemann reaction. This process achieves a 67% yield and leads to further saponification and decarboxylation, producing 3-fluorothiophene with a 93% yield (Pomerantz & Turkman, 2008).

Intermediate in Aminofluorothiophene Synthesis

It has been used as an intermediate in the attempted synthesis of 2-amino-3-fluorothiophene. The synthesis process involved a Schiemann reaction of the 3-diazonium salt in xylenes, highlighting the compound's importance in producing complex chemical structures (Kobarfard, Kauffman, & Boyko, 1999).

Production of α-Carboxy-γ-Fluorothiophenes

A new method for synthesizing substituted α-carboxy-γ-fluorothiophenes has been reported, where methyl 3-fluorothiophene-2-carboxylate reacts with methyl thioglycolate anion and α-fluoro-β-(phenylthio)enones. This method demonstrates the compound's role in creating novel thiophene derivatives (Andrès, Laurent, & Marquet, 1997) .

In Copper-Mediated N-Arylation

The compound is involved in copper-mediated N-arylation processes, specifically for the synthesis of N-arylated methyl 2-aminothiophene-3-carboxylate. This showcases its utility in cross-coupling reactions and the synthesis of complex organic molecules (Rizwan et al., 2015).

Safety And Hazards

Methyl 3-fluorothiophene-2-carboxylate is classified as a warning substance. It can cause skin irritation, serious eye irritation, and may cause respiratory irritation. Therefore, it is recommended to wear protective gloves, protective clothing, eye protection, and face protection when handling this compound.

Relevant Papers Several peer-reviewed papers and technical documents related to Methyl 3-fluorothiophene-2-carboxylate are available. These documents provide more detailed information about the compound’s synthesis, properties, and potential applications.

More Information