Dicyclohexylcarbodimide (DCC) is an organic compound used primarily for coupling amino acids in peptide synthesis, existing as white crystals with a sweet odor. It is soluble in various organic solvents but is moisture-sensitive and considered a potent allergen. DCC is involved in the Moffatt oxidation process to convert alcohols into aldehydes and ketones, via a specific reaction mechanism involving organosulfur intermediates.

1. DICYCLOHEXYLCARBODIMIDE
(DCC)

2. DICYCLOHEXYLCARBODIMIDE
(C13H22N2)
• N,N’-Dicyclohexylcarbodimide is an organic
compound
• The important use to couple amino acids
during artificial peptide synthesis
• The compound is abbreviated as DCC, DCCD or
DCCI

3. PROPERTIES
• Under standard condition, it exists in the from
of white crystals with a heavy, sweet odor.
• The low melting point (30-350C)
• Boiling point 122-1240C
• Soluble in tetrahydrofuran, acetonitrile and
dimethylformamide dichloromethane, but
insoluble in water stable, but moisture
sensitive.

4. SAFETY PRECAUTION
• DCC is a potent allergen and a sensitizer, and
causing skin rashes.

6. SYNTHESIS
• It can also be prepared by oxidation of
dicyclohexylurea with p-toluene sulfonyl chloride in
hot pyridine or by heating dicyclohexylthiourea with
yellow mercuric oxide

7. APPLICATION
1. MOFFATT OXIDATION
• Moffatt oxidation is the oxidation of primary and secondary
alcohol in presence of dimethyl sulfoxide (DMSO) and
dicychexylcarbodimide (DCC) To form a alkoxysulfonium ylide
intermediate, which rearranges to from aldehydes and
ketones

9. MECHANISM
• Dicyclohexyl carbodiimide (1) is attacked by
dimethyl sulfoxide to from an intermediate (2)
• It is then promotated by the addition of the
alcohol oxygen on the sulfur atom
• Then a stable dicyclohexyl urea (4) is formed
along with sulfenate salt (3)
• It then react with a dihydeogen
phosphateanion to from ketone

12. THANK YOU