Tetrahydrofuran-2-carboxylic acid
Overview
(R)-Tetrahydrofuran-2-carboxylic Acid ((R)-THFCA) is a chiral carboxylic acid derived from tetrahydrofuran. It serves as a versatile intermediate in organic synthesis, particularly in the pharmaceutical industry where enantiomeric purity is critical. Its chiral nature makes it valuable for producing optically active compounds. The compound is synthesized through asymmetric methods or resolution techniques to ensure high enantiomeric excess (ee). Its applications span from active pharmaceutical ingredients (APIs) to specialty chemicals, where its structural features contribute to desired stereochemical outcomes.
Physical and Chemical Properties
(R)-THFCA is a colorless to pale yellow liquid at room temperature, with a molecular weight of 116.11 g/mol. It exhibits good solubility in polar solvents like water, methanol, and ethanol, facilitating its use in reaction media. The compound's density is approximately 1.15 g/cm³, though precise values depend on temperature and purity. Its stability under typical storage conditions makes it suitable for industrial use, but it should be protected from strong oxidizers and excessive heat. The chiral center at the 2-position of the tetrahydrofuran ring is crucial for its role in asymmetric synthesis.
Main Applications
(R)-THFCA is primarily employed in the synthesis of chiral drugs and fine chemicals. It acts as a building block for prostaglandins, antiviral agents, and other bioactive molecules requiring specific stereochemistry. The pharmaceutical industry values its predictability in enantioselective reactions. Additionally, it serves as a ligand or catalyst in asymmetric catalysis, enhancing the efficiency of producing single-enantiomer products. Its use extends to agrochemicals and flavors, where chirality influences biological activity and sensory properties.
Safety and Storage
While (R)-THFCA is not classified as highly hazardous, proper handling is essential to avoid irritation or sensitization. Use gloves and goggles when handling, and ensure adequate ventilation. Storage should be in tightly sealed containers, away from direct sunlight and oxidizing agents. In case of spills, absorb with inert material and dispose of according to local regulations. Long-term stability is maintained at temperatures below 25°C, preferably in a nitrogen atmosphere to prevent degradation.
B2B Procurement Guide
When procuring (R)-THFCA, prioritize suppliers with documented quality control processes, especially for chiral purity (e.g., ≥98% ee). Request certificates of analysis (CoA) and batch-specific data. Pricing varies based on scale and purity, with bulk orders typically attracting discounts. Consider logistical factors such as packaging (drums vs. smaller containers) and lead times. For pharmaceutical applications, ensure compliance with Good Manufacturing Practice (GMP) standards. Auditing supplier facilities or opting for reputed manufacturers minimizes risks.