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8.02954

Sigma-Aldrich

N,N′-Dicyclohexylcarbodiimide

for synthesis

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Synonym(s):
N,N′-Dicyclohexylcarbodiimide, DCC
Linear Formula:
C(NC6H11)2
CAS Number:
538-75-0
Molecular Weight:
206.33
EC Index Number:
208-704-1

Quality Level

200

form

solid

potency

1110 mg/kg LD50, oral (Rat)
71 mg/kg LD50, skin (Rat)

reaction suitability

reaction type: Coupling Reactions

bp

148-152 °C/15 hPa

mp

35-36 °C

transition temp

flash point 113 °C

density

0.95 g/cm3 at 40 °C

bulk density

920 kg/m3

application(s)

peptide synthesis

storage temp.

2-30°C

InChI

1S/C13H22N2/c1-3-7-12(8-4-1)14-11-15-13-9-5-2-6-10-13/h12-13H,1-10H2

InChI key

QOSSAOTZNIDXMA-UHFFFAOYSA-N

Related Categories

General description

N,N′-Dicyclohexylcarbodiimide (DCC) is a highly versatile dehydrating reagent with varied applications in organic chemistry. It is most frequently used as a coupling agent for the synthesis of amides, esters and thioesters from carboxylic acids and amines, alcohol and thiols, respectively. In peptide synthesis applications, DCC is used in conjunction with auxiliary nucleophiles such as Oxyma Pure and HOBt, to minimize side reactions such as racemization, N-acylurea or oxazolone formation. It is used as a dehydration reagent in the Moffatt oxidation of primary alcohols to aldehydes and in the conversion of amides to nitriles. The by-product of the dehydration reaction, dicyclohexylurea, is sparingly soluble in most reaction solvents and can be removed by filtration.

Application

Recent applications of N,N′-Dicyclohexylcarbodiimide include:
  • The synthesis of optically pure N-acyl-N,N′-dicyclohexylureas.
  • The activation of the carboxylic acid groups in aromatic carboxylic acids to facilitates their reaction with (N-isocyanimino)trifluoroacetamide to form the corresponding 1,3,4-oxadiazole derivatives.
  • The synthesis of poly (vinyl alcohol-co-vinyl levulinate) copolymers for use in biomedical applications.

Pictograms

CorrosionSkull and crossbones
GHS05,GHS06

Signal Word

Danger

Hazard Statements

H302 - H311 - H317 - H318

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 4 Oral - Eye Dam. 1 - Skin Sens. 1

Storage Class Code

6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

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Dicyclohexylcarbodiimide
Albert, J. S. et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition, 1-9 (2017)
Synthesis of sterically congested 1, 3, 4-oxadiazole derivatives from aromatic carboxylic acids, N, N-dicyclohexylcarbodiimide and (N-isocyanimino) triphenylphosphorane
Nasrabadi FZ, et al.
Molecular Diversity, 791-798 (2011)
Formation of optically pure N-acyl-N, N?-dicyclohexylurea in N, N?-dicyclohexylcarbodiimide-mediated peptide synthesis
SLEBIODA, M, et al.
International Journal of Peptide and Protein Research, 35, 539-541 (1990)
N, N-dicyclohexylcarbodiimide assisted synthesis and characterization of poly (vinyl alcohol-co-vinyl levulinate
Wang YM, et al.
Polymer, 9793-9802 (2005)

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