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

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

Names
IUPAC name 3-(Ethyliminomethyleneamino)-N,N-dimethylpropan-1-amine
Identifiers
CAS Number	1892-57-5
ChemSpider	15119
Jmol interactive 3D	Image
PubChem	15908
InChI InChI=1S/C8H17N3/c1-4-9-8-10-6-5-7-11(2)3/h4-7H2,1-3H3 Key: LMDZBCPBFSXMTL-UHFFFAOYSA-N InChI=1/C8H17N3/c1-4-9-8-10-6-5-7-11(2)3/h4-7H2,1-3H3 Key: LMDZBCPBFSXMTL-UHFFFAOYAH
SMILES CCN=C=NCCCN(C)C
Properties
Chemical formula	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

• López-Alonso, JP; Diez-Garcia, F; Font, J; Ribó, M; Vilanova, M; Scholtz, JM; González, C; Vottariello, F; Gotte, G; Libonati, M; Laurents, DV (2009). "Carbodiimide EDC Induces Cross-Links That Stabilize RNase A C-dimer against Dissociation: EDC Adducts Can Affect Protein Net Charge, Conformation and Activity". Bioconjug Chem. 20 (8): 1459. doi:10.1021/bc9001486.
• Nakajima, N; Ikada, Y (1995). "Mechanism of Amide Formation by Carbodiimide for Bioconjugation in Aqueous Media". Bioconjug Chem. 6: 123. doi:10.1021/bc00031a015.

External links

• EDCI coupling - Synthetic protocols from organic-reaction.com