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

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

3-(Ethyliminomethyleneamino)-N,N-dimethylpropan-1-amine

Identifiers
CAS number 1892-57-5 YesY
PubChem 15908
ChemSpider 15119 YesY
Jmol-3D images Image 1
Properties
Molecular formula C8H17N3
Molar mass 155.24 g mol−1
Hazards
MSDS External MSDS (HCl salt)
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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) or sulfo-NHS to increase coupling efficiency by creating a more reactive amine- product.

EDC is also used in organic chemistry to couple a carboxylic acid to alcohol using DMAP as a catalyst.

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. 
  • Skotnicki, S; Kearney, RM; Smith, AL (1994). "Synthesis of secorapamycin esters and amides". Tetrahedron Lett. 35 (21): 197. doi:10.1016/S0040-4039(00)76509-9. 

External links

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