N,N'-Dicyclohexylcarbodiimide is a carboxyl activating reagent used in peptide synthesis. It acts as a dehydrating agent for the preparation of amides, ketones and nitriles. It is involved in the preparation of esters by reacting tertiary alcohols with carboxylic acid. It is utilized for the stereo chemical inversion of secondary alcohols by forming formyl ester followed by saponification. It is associated with dimethyl sulfoxide and used in Pfitzner-Moffatt oxidation to convert alcohols into aldehydes and ketones.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
N,N′-Dicyclohexylcarbodiimide is a carboxyl activating reagent used in peptide synthesis. It acts as a dehydrating agent for the preparation of amides, ketones and nitriles. It is involved in the preparation of esters by reacting tertiary alcohols with carboxylic acid. It is utilized for the stereo chemical inversion of secondary alcohols by forming formyl ester followed by saponification. It is associated with dimethyl sulfoxide and used in Pfitzner-Moffatt oxidation to convert alcohols into aldehydes and ketones.
Solubility
Soluble in methanol, chloroform, dichloromethane, acetonitrile, tetrahydrofuran and dimethylformamide. Insoluble in water.
Notes
Incompatible with strong oxidizing agents.
RUO – Research Use Only
General References:
- Blbulyan, S.; Trchounian, A. Impact of membrane-associated hydrogenases on the F O F 1-ATPase in Escherichia coli during glycerol and mixed carbon fermentation: ATPase activity and its inhibition by N, N'-dicyclohexylcarbodiimide in the mutants lacking hydrogenases. Arch. Biochem. Biophys. 2015, 579, 67-72.
- Chen, J.; Zhang, J.; Zhang, W.; Chen, Z. Sensitive determination of the potential biomarker sarcosine for prostate cancer by LC-MS with N, N'-dicyclohexylcarbodiimide derivatization. J. Sep. Sci. 2014, 37 (1-2), 14-19.