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36650

Sigma-Aldrich

DCC

puriss., ≥99.0% (GC)

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

grade

puriss.

Quality Level

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.

Packaging

100, 500 g in poly bottle
2.5 kg in poly bottle

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

Signal Word

Danger

Hazard Statements

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

Certificate of Analysis

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Certificate of Origin

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