EDC HCl: A Versatile Coupling Reagent in Organic Synthesis

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC HCl) is a widely used coupling reagent in organic and peptide synthesis. It plays a crucial role in facilitating the formation of amide and ester bonds, making it indispensable in biochemical and pharmaceutical research.

Chemical Properties

• Molecular Formula: C₈H₁₇N₃ · HCl

• Molar Mass: 191.70 g/mol

• Solubility: Highly soluble in water and organic solvents like DMF and DMSO

• Appearance: White to off-white crystalline powder

• Stability: Sensitive to moisture; should be stored in a dry environment

Mechanism of Action

EDC HCl activates carboxyl groups by forming an O-acylisourea intermediate, which then reacts with nucleophiles such as amines to form amide bonds. Unlike other carbodiimide reagents (e.g., DCC), EDC is water-soluble, making it easier to remove after the reaction. Many EDC HCl manufacturer supply high-purity reagents for pharmaceutical and biochemical applications.

Applications

1. Peptide Synthesis

   • Used to couple amino acids efficiently in peptide bond formation.

   • Often used with N-hydroxysuccinimide (NHS) to improve reaction yields.

2. Protein and DNA Conjugation

   • Facilitates the crosslinking of proteins, enzymes, and nucleic acids.

   • Commonly used in bioconjugation techniques.

3. Carbodiimide Chemistry

   • Assists in the synthesis of esters and other bioactive molecules.

   • Plays a role in modifying biomaterials for medical applications.

Advantages of EDC HCl

• Water Solubility: Unlike DCC, EDC HCl dissolves in aqueous and organic media.

• High Efficiency: Works effectively at room temperature.

• Less Byproduct Formation: Forms a water-soluble urea byproduct, simplifying purification.

Safety and Handling

• Irritant: Can cause skin and eye irritation.

• Proper Storage: Must be kept dry to prevent hydrolysis.

• Use PPE: Gloves, goggles, and fume hoods are recommended when handling.

Conclusion

EDC HCl is a powerful and versatile reagent in synthetic and biochemical research. Its efficiency, water solubility, and ease of use make it a preferred choice for amide bond formation and biomolecular conjugation. However, due to its sensitivity to moisture, careful storage and handling are essential for optimal performance. Tempo Free Radical is widely used as a catalyst in oxidation reactions and polymer chemistry.