Carbonyldiimidazole (CDI), known by its CAS number 530-62-1, is a highly versatile and frequently used reagent in organic synthesis. Its utility stems from its ability to activate carboxylic acids, making it an excellent coupling agent for forming amide, ester, and carbamate bonds. For chemists seeking efficient and mild reaction conditions, CDI offers a practical solution.
Understanding CDI's Properties:CDI typically appears as a white to off-white powder. It is known for its reactivity with moisture, so proper storage in a dry environment is crucial. Its key advantage lies in its ability to activate carboxylic acids by forming a highly reactive acyl imidazole intermediate. This intermediate then readily reacts with nucleophiles like amines and alcohols.
Key Applications in Synthesis:- Peptide Synthesis: CDI is widely used to couple amino acids, forming peptide bonds efficiently under mild conditions, which is essential for creating peptides and proteins for research and therapeutic purposes.
- Amide and Ester Formation: It serves as a reliable reagent for converting carboxylic acids into amides by reacting with amines, and into esters by reacting with alcohols.
- Pharmaceutical Intermediates: CDI is instrumental in the synthesis of various pharmaceutical intermediates, contributing to the development of new drugs.
- Heterocyclic Chemistry: It can be employed in cyclization reactions to form diverse heterocyclic organic compounds, which are prevalent in medicinal chemistry.
Tips for Effective Use:- Moisture Sensitivity: Always handle CDI in a dry atmosphere. Use freshly opened reagent or ensure proper re-sealing of containers.
- Stoichiometry: Use the appropriate molar equivalents of CDI for your reaction to ensure complete activation and minimize unreacted starting materials. Typically, one equivalent of CDI is used per mole of carboxylic acid.
- Solvent Choice: CDI is soluble in common organic solvents such as THF, DMF, and acetonitrile. Ensure the solvent is dry.
- Reaction Conditions: Reactions involving CDI can often be performed at room temperature, but optimization might be needed depending on the specific substrates.
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