The Chemical Properties and Synthesis of 5-Chlorothiophene-2-carboxylic Acid
Understanding the fundamental chemical properties and synthesis routes of key intermediates is crucial for their effective utilization in various industrial and research applications. 5-Chlorothiophene-2-carboxylic acid, identified by CAS number 24065-33-6, is a prominent example of such a compound, valued for its distinctive characteristics and synthetic accessibility.
Chemically, 5-Chlorothiophene-2-carboxylic acid possesses the molecular formula C5H3ClO2S and a molecular weight of approximately 162.59 g/mol. Its appearance is typically described as a white to light yellow crystalline powder. A key physical property is its melting point, which generally falls within the range of 148-156 °C, indicating a stable solid form under standard conditions. This stability, combined with its reactive functional groups – the carboxylic acid and the chlorinated thiophene ring – makes it a highly adaptable intermediate in organic chemistry.
The synthesis of 5-Chlorothiophene-2-carboxylic acid can be achieved through several well-documented pathways. As previously mentioned, one effective route involves starting with 2-chlorothiophene. This material undergoes Friedel-Crafts acylation using trichloroacetyl chloride in the presence of aluminum trichloride to form 2-trichloroacetyl-5-chlorothiophene. Subsequent alkaline hydrolysis then yields the target carboxylic acid. Another common method relies on the preparation of a Grignard reagent from 5-chloro-2-bromothiophene, followed by carboxylation with carbon dioxide and acid treatment.
A third synthesis strategy utilizes 5-chloro-2-acetylthiophene as the starting material. This precursor is then oxidized using a system comprising sodium chlorite and potassium dihydrogen phosphate, leading to the formation of 5-Chlorothiophene-2-carboxylic acid. Each of these methods has been optimized to achieve high yields and purity, reflecting the compound's importance in chemical manufacturing.
The applications of 5-Chlorothiophene-2-carboxylic acid are diverse, ranging from its critical role as an intermediate in the synthesis of pharmaceuticals such as Rivaroxaban, to its use in the agrochemical sector for creating herbicides and fungicides. Its utility also extends to materials science, where it is explored as a precursor for functional polymers.
For researchers and manufacturers, understanding these properties and synthesis methods is key to leveraging the full potential of 5-Chlorothiophene-2-carboxylic acid. Access to detailed technical specifications, including purity assays (often by HPLC) and clear synthesis protocols, ensures efficient and successful integration into various chemical processes. Reliable suppliers, particularly those in China with a strong track record in fine chemical production, are essential for obtaining this compound with the required quality and consistency.
In summary, 5-Chlorothiophene-2-carboxylic acid is a compound of significant chemical interest due to its defined properties and accessible synthesis routes. Its role as a versatile intermediate across multiple sectors highlights its continued importance in advancing chemical research and industrial applications.
Chemically, 5-Chlorothiophene-2-carboxylic acid possesses the molecular formula C5H3ClO2S and a molecular weight of approximately 162.59 g/mol. Its appearance is typically described as a white to light yellow crystalline powder. A key physical property is its melting point, which generally falls within the range of 148-156 °C, indicating a stable solid form under standard conditions. This stability, combined with its reactive functional groups – the carboxylic acid and the chlorinated thiophene ring – makes it a highly adaptable intermediate in organic chemistry.
The synthesis of 5-Chlorothiophene-2-carboxylic acid can be achieved through several well-documented pathways. As previously mentioned, one effective route involves starting with 2-chlorothiophene. This material undergoes Friedel-Crafts acylation using trichloroacetyl chloride in the presence of aluminum trichloride to form 2-trichloroacetyl-5-chlorothiophene. Subsequent alkaline hydrolysis then yields the target carboxylic acid. Another common method relies on the preparation of a Grignard reagent from 5-chloro-2-bromothiophene, followed by carboxylation with carbon dioxide and acid treatment.
A third synthesis strategy utilizes 5-chloro-2-acetylthiophene as the starting material. This precursor is then oxidized using a system comprising sodium chlorite and potassium dihydrogen phosphate, leading to the formation of 5-Chlorothiophene-2-carboxylic acid. Each of these methods has been optimized to achieve high yields and purity, reflecting the compound's importance in chemical manufacturing.
The applications of 5-Chlorothiophene-2-carboxylic acid are diverse, ranging from its critical role as an intermediate in the synthesis of pharmaceuticals such as Rivaroxaban, to its use in the agrochemical sector for creating herbicides and fungicides. Its utility also extends to materials science, where it is explored as a precursor for functional polymers.
For researchers and manufacturers, understanding these properties and synthesis methods is key to leveraging the full potential of 5-Chlorothiophene-2-carboxylic acid. Access to detailed technical specifications, including purity assays (often by HPLC) and clear synthesis protocols, ensures efficient and successful integration into various chemical processes. Reliable suppliers, particularly those in China with a strong track record in fine chemical production, are essential for obtaining this compound with the required quality and consistency.
In summary, 5-Chlorothiophene-2-carboxylic acid is a compound of significant chemical interest due to its defined properties and accessible synthesis routes. Its role as a versatile intermediate across multiple sectors highlights its continued importance in advancing chemical research and industrial applications.
Perspectives & Insights
Chem Catalyst Pro
“Understanding the fundamental chemical properties and synthesis routes of key intermediates is crucial for their effective utilization in various industrial and research applications.”
Agile Thinker 7
“5-Chlorothiophene-2-carboxylic acid, identified by CAS number 24065-33-6, is a prominent example of such a compound, valued for its distinctive characteristics and synthetic accessibility.”
Logic Spark 24
“Chemically, 5-Chlorothiophene-2-carboxylic acid possesses the molecular formula C5H3ClO2S and a molecular weight of approximately 162.”