1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide
Skeletal formula of EDC
Ball-and-stick model of the EDC molecule
Names
IUPAC name
3-(Ethyliminomethyleneamino)-N,N-dimethylpropan-1-amine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.015.982
Properties
C8H17N3
Molar mass 155.25 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC, EDAC or EDCI) is a water-soluble carbodiimide usually obtained as the hydrochloride. It is typically employed in the 4.0-6.0 pH range. It is generally used as a carboxyl activating agent for the coupling of primary amines to yield amide bonds. Additionally, EDC can also be used to activate phosphate groups in order to form phosphomono-esters and phosphodiesters. Common uses for this carbodiimide include peptide synthesis, protein crosslinking to nucleic acids, but also in the preparation of immunoconjugates. EDC is often used in combination with N-hydroxysuccinimide (NHS) for the immobilisation of large biomolecules.

Preparation

EDC is commercially available. It may be prepared by coupling ethyl isocyanate with N,N-dimethylpropane-1,3-diamine to give a urea, followed by dehydration:[1]

References

  1. ↑ Sheehan, John; Cruickshank, Philip; Boshart, Gregory (1961). "A Convenient Synthesis of Water-Soluble Carbodiimides". J. Org. Chem. 26 (7): 2525. doi:10.1021/jo01351a600.

Further reading

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