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Merck
CN

36650

DCC

≥99.0% (GC), for peptide synthesis

Synonym(s):

N,N′-Dicyclohexylcarbodiimide

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About This Item

Linear Formula:
C6H11N=C=NC6H11
CAS Number:
538-75-0
Molecular Weight:
206.33
NACRES:
NA.22
PubChem Substance ID:
329755430
UNSPSC Code:
12352000
EC Number:
208-704-1
MDL number:
MFCD00011659
Beilstein/REAXYS Number:
610662

Key Documents

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Product Name

DCC, puriss., ≥99.0% (GC)

InChI key

QOSSAOTZNIDXMA-UHFFFAOYSA-N

InChI

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

SMILES string

C1CCC(CC1)N=C=NC2CCCCC2

grade

puriss.

assay

≥99.0% (GC)

form

solid

reaction suitability

reaction type: Coupling Reactions

bp

122-124 °C/6 mmHg (lit.)

mp

32.0-37.0 °C
34-35 °C (lit.)

solubility

methylene chloride: 0.1 g/mL, clear, colorless

application(s)

peptide synthesis

Quality Level

200

Gene Information

human ... EPHX2(2053)
mouse ... Ephx2(13850)

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Application

DCC may be used to promote the esterification of 7-((tert-butyldimethylsilyl)oxy)hepta-2,4-diyn-1-ol with propiolic acid to form 7-((tert-butyldimethylsilyl)oxy)hepta-2,4-diyn-1-yl propynoate.
It may be also used to synthesize:
  • 1,3-Thiazetedine derivatives via [2+2] cycloaddition with 2-phenylethenyl- and 2-(4-nitrophenyl)ethenyl isothiocyanates.
  • 1,3,5-Oxadiazine-4-thiones via [4+2] cycloaddition with benzoyl isothiocyanates.
  • Sterically hindered 1,3,4-oxadiazole derivatives by reacting with (N-isocyanimino)triphenylphosphorane the presence of aromatic (or heteroaromatic) carboxylic acids.

General description

DCC is an organic compound widely used as a coupling reagent in peptide synthesis. It is also employed as an efficient dehydrating agent for the preparation of amides, esters, nitriles, and anhydrides. Alcohols can be converted into aldehydes and ketone by Moffatt oxidation reaction in the presence of DCC and dimethyl sulfoxide (DMSO).

Other Notes

Coupling reagent, reagent for dehydrations etc. Modifies bovine heart mitochondrial transhydrogenase; Inhibition of F1F0-ATPase and other proton-translocating enzymes

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

6.1D - 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

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF7239V
WXBF6290V
WXBF5886V
WXBF2470V
WXBF4739V

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Dicyclohexylcarbodiimide (DCC)
Kvasnica M
Synlett, 2007(14), 2306-2307 (2007)
M. Solioz
Trends in Biochemical Sciences, 9, 309-309 (1984)
Light-dependent chemical modification of thylakoid membrane protein with carboxyl-directed reagents.
J A Laszlo et al.
Archives of biochemistry and biophysics, 215(2), 571-581 (1982-05-01)
M Slebioda et al.
International journal of peptide and protein research, 35(6), 539-541 (1990-06-01)
N-acylurea, a side product in peptide synthesis from DCC, preserves its chiral integrity although peptides formed simultaneously in the same reaction are racemized to a large extent. This observation is inconsistent with the generally accepted opinion that racemization-prone O-acylisourea is
Review of synthesis of 1, 3, 4-oxadiazole derivatives.
Patel K D, et al.
Synthetic Communications, 44(13), 1859-1875 (2014)
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