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36650

Sigma-Aldrich

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
Beilstein:
610662
EC Number:
208-704-1
MDL number:
MFCD00011659
UNSPSC Code:
12352000
PubChem Substance ID:
329755430
NACRES:
NA.22

product name

DCC, puriss., ≥99.0% (GC)

grade

puriss.

Quality Level

200

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

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 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).

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.

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

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
WXBD6453V
WXBD6647V
WXBD3874V
WXBD2750V
WXBD1829V

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Review of synthesis of 1, 3, 4-oxadiazole derivatives.
Patel K D, et al.
Synthetic Communications, 44(13), 1859-1875 (2014)
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)
R M Pennington et al.
The Journal of biological chemistry, 256(17), 8963-8969 (1981-09-10)
Dicyclohexylcarbodiimide (DCCD) inhibits the reduction of oxidized 3-acetylpyridine adenine dinucleotide (AcPyAD+) by NADPH catalyzed by purified and bovine heart submitochondrial particle transhydrogenase. Kinetic studies demonstrate that the modification of 1 residue results in complete inactivation. Both transhydrogenase preparations were labeled
M. Solioz
Trends in Biochemical Sciences, 9, 309-309 (1984)
Dicyclohexylcarbodiimide (DCC)
Kvasnica M
Synlett, 2007(14), 2306-2307 (2007)
View All Related Papers

Articles

Coupling Reagents

In principle, the seemingly simple formation of a peptide bond can be accomplished using all the procedures available in organic chemistry for the synthesis of carboxylic acid amides. However, due to the presence of various functional groups in natural and unnatural amino acids and particularly the requirement for full retention of chiral integrity, the coupling of amino acids and peptides under mild conditions can be challenging. A plethora of coupling reagents has been developed superseding each other in efficiency and suitability for specific applications (e.g., solid-phase peptide synthesis or fragment condensation).

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