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36650 Sigma-Aldrich

DCC

puriss., ≥99.0% (GC)

Synonym: N,N′-Dicyclohexylcarbodiimide

  • CAS Number 538-75-0

  • Linear Formula C6H11N=C=NC6H11

  • Molecular Weight 206.33

  •  Beilstein/REAXYS Number 610662

  •  EC Number 208-704-1

  •  MDL number MFCD00011659

  •  PubChem Substance ID 329755430

  •  NACRES NA.22

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Properties

Related Categories Carbodiimides, Chemical Biology, Chemical Synthesis, Coupling, Peptide Coupling,
Quality Level   200
grade   puriss.
assay   ≥99.0% (GC)
bp   122-124 °C/6 mmHg (lit.)
mp   34-35 °C (lit.)
  34.5-37.0 °C
solubility   methylene chloride: 0.1 g/mL, clear, colorless
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)

Description

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

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
3
RTECS 
FF2160000
Flash Point(F) 
235.4 °F
Flash Point(C) 
113 °C

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

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...
Matthias Junkers
Aldrich ChemFiles 2007, 7.2, 3.
Keywords: Acylations, Catalysis, Condensations, Dehydration reaction, Peptide synthesis, Racemizations, Solid phase peptide synthesis

Peer-Reviewed Papers
15

References

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