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D80002

Sigma-Aldrich

DCC

99%

Synonym(s):

N,N′-Dicyclohexylcarbodiimide

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25 G
$24.90
100 G
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500 G
$127.00
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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
form:
solid
assay:
99%

$24.90

In StockDetails

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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.[1] It mediates the esterification of poly(vinyl alcohol) with free levulinic acid to form poly(vinyl alcohol-co-vinyl levulinate).[2]

Application

Carboxy group activating reagent for peptide synthesis.[3]
DCC has been used in the preparation of titanate nanotubes-phthalocyanine(TiONts-Pc) nanohybrids[4] and 7-((tert-butyldimethylsilyl)oxy)hepta-2,4-diyn-1-yl propynoate.[5]
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.[6]
It can also used to synthesize:
  • 1,3-Thiazetedine derivatives via [2+2] cycloaddition with 2-phenylethenyl- and 2-(4-nitrophenyl)ethenyl isothiocyanates.[7]
  • 1,3,5-Oxadiazine-4-thiones via [4+2] cycloaddition with benzoyl isothiocyanates.[8]
  • Sterically hindered 1,3,4-oxadiazole derivatives by reacting with (N-isocyanimino)triphenylphosphorane in the presence of aromatic (or heteroaromatic) carboxylic acids.[9]

pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

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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_germany

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
WXBF5003V
WXBF3711V
WXBF4159V
WXBF2469V
WXBF4740V

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4-(Dimethylamino)pyridine for synthesis

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)
Svenja Bockelmann et al.
The Journal of biological chemistry, 285(49), 38304-38314 (2010-10-05)
The macrolactone archazolid is a novel, highly specific V-ATPase inhibitor with an IC(50) value in the low nanomolar range. The binding site of archazolid is presumed to overlap with the binding site of the established plecomacrolide V-ATPase inhibitors bafilomycin and
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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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