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D80002

Sigma-Aldrich

DCC

99%

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
Beilstein/REAXYS Number:
610662
EC Number:
208-704-1
MDL number:
MFCD00011659
UNSPSC Code:
12352111
PubChem Substance ID:
24894174
NACRES:
NA.22

Quality Level

200

assay

99%

form

solid

reaction suitability

reaction type: Coupling Reactions

bp

122-124 °C/6 mmHg (lit.)

mp

34-35 °C (lit.)

SMILES string

C1CCC(CC1)N=C=NC2CCCCC2

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

Gene Information

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

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General description

DCC is the acronym for N,N′-dicyclohexylcarbodiimide. In peptide synthesis, it is utilized for the activation of carboxyl group. The structure of DCC has been analyzed based on IR and Raman spectral data. It mediates the esterification of poly(vinyl alcohol) with free levulinic acid to form poly(vinyl alcohol-co-vinyl levulinate).

Application

Carboxy group activating reagent for peptide synthesis.
DCC has been used in the preparation of titanate nanotubes-phthalocyanine(TiONts-Pc) nanohybrids and 7-((tert-butyldimethylsilyl)oxy)hepta-2,4-diyn-1-yl propynoate.
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 can 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 in the presence of aromatic (or heteroaromatic) carboxylic acids.

pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

signalword

Danger

Hazard Classifications

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

wgk_germany

WGK 3

flash_point_f

closed cup

flash_point_c

closed cup

ppe

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

Certificates of Analysis (COA)

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Sigma-Aldrich

8.20499

4-(Dimethylamino)pyridine

N,N-dicyclohexylcarbodiimide assisted synthesis and characterization of poly (vinyl alcohol-co-vinyl levulinate).
Wang, YM, et al.
Polymer, 46(23), 9793-9802 (2005)
Vibrational spectroscopy and DFT calculations of N,N'-dicyclohexylcarbodiimide.
Chowdhry BZ, et al.
Journal of Raman Spectroscopy, 42(2), 230-238 (2011)
Jones, J.
The Chemical Synthesis of Peptides, International Series of Monographs on Chemistry, 23 (1994)
Phthalocyanine-titanate nanotubes: a promising nanocarrier detectable by optical imaging in the so-called imaging window.
Paris J, et al.
Royal Society of Chemistry Advances, 5(9), 6315-6322 (2015)
Reaction of 4-substituted benzoyl isothiocyanates with N, N'-dicyclohexylcarbodiimide and N, N'-diphenylcarbodiimide
Hritzova O
Collection of Czechoslovak Chemical Communications, 43(12), 3258-3262 (1978)
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