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8.02954

N,N′-Dicyclohexylcarbodiimide

for peptide synthesis

Synonym(s):

N,N′-Dicyclohexylcarbodiimide, DCC

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About This Item

Linear Formula:
C(NC6H11)2
CAS Number:
538-75-0
Molecular Weight:
206.33
MDL number:
MFCD00011659
UNSPSC Code:
12352111
EC Index Number:
208-704-1
NACRES:
NA.22
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Product Name

N,N′-Dicyclohexylcarbodiimide, for synthesis

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

SMILES string

N(=C=NC2CCCCC2)C1CCCCC1

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

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

Skull and crossbonesCorrosion
GHS06,GHS05

signalword

Danger

Hazard Classifications

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

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

Certificates of Analysis (COA)

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N, N-dicyclohexylcarbodiimide assisted synthesis and characterization of poly (vinyl alcohol-co-vinyl levulinate
Wang YM, et al.
Polymer, 9793-9802 (2005)
Dicyclohexylcarbodiimide
Albert, J. S. et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition, 1-9 (2017)
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)
View All Related Papers

Global Trade Item Number

SKUGTIN
802954100004022536377414
802954400004022536662459
802954250004022536377421
802954500004022536759807
802954025004022536377407