N,N'-Dicyclohexylcarbodiimide

N,N'-Dicyclohexylcarbodiimide (also known as DCC or DCCD) is a chemical compound with the formula (C6H11N)2. It is a waxy white solid with a sweet odor. DCC is a reagent used in organic chemistry for the synthesis of amides and esters. It is also used in biochemistry for the modification of proteins.

Chemical Structure and Properties

Chemical structure of N,N'-Dicyclohexylcarbodiimide

DCC has a symmetrical structure, with two cyclohexyl groups attached to a central carbodiimide functional group (-N=C=N-). The molecule is nonpolar and has a relatively high melting point (34-35 °C) due to the strong intermolecular forces between the cyclohexyl groups. DCC is soluble in organic solvents such as dichloromethane, tetrahydrofuran, and dimethylformamide.

Synthesis

DCC is synthesized by the reaction of cyclohexylamine with phosgene. The reaction proceeds via the formation of an intermediate isocyanate, which then reacts with a second molecule of cyclohexylamine to form DCC.

Uses

DCC is primarily used in organic chemistry as a dehydration reagent for the synthesis of amides and esters from carboxylic acids. It is also used in biochemistry for the modification of proteins, specifically in the inhibition of proton pumps and ATPase enzymes.

Safety

DCC is a skin and eye irritant and may cause allergic reactions. It should be handled with care, using appropriate personal protective equipment.

See Also

• Carbodiimide
• Peptide synthesis
• Protein modification