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Sigma-Aldrich

DCC

puriss., ≥99.0% (GC)

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Synonym(s):
N,N′-Dicyclohexylcarbodiimide
Linear Formula:
C6H11N=C=NC6H11
CAS Number:
538-75-0
Molecular Weight:
206.33
Beilstein:
610662
EC Number:
208-704-1
MDL number:
MFCD00011659
PubChem Substance ID:
329755430
NACRES:
NA.22

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

CorrosionSkull and crossbones
GHS05,GHS06

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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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)
Review of synthesis of 1, 3, 4-oxadiazole derivatives.
Patel K D, et al.
Synthetic Communications, 44(13), 1859-1875 (2014)
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
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
Dicyclohexylcarbodiimide (DCC)
Kvasnica M
Synlett, 2007(14), 2306-2307 (2007)
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