10328. EDC

Nomenclature

CAS number: 1892-57-5
N3-(Ethylcarbonimidoyl)-N1,N1-dimethyl-1,3-propanediamine; N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide; 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide; N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide; EDAC; EDCI.
C8H17N3; mol wt 155.24.
C 61.89%, H 11.04%, N 27.07%.

Description and references

Peptide coupling reagent frequently used to synthesize amide bonds. Exists as a mixture with its cyclic tautomer. Prepn of parent and derivatives: J. C. Sheehan et al., J. Org. Chem. 26, 2525 (1961) DOI. Tautomerism studies: T. Tenforde et al., ibid. 37, 3372 (1972) DOI; and reaction mechanism studies: A. Williams, I. T. Ibrahim, J. Am. Chem. Soc. 103, 7090 (1981) DOI. Spectrophotometric determn: K. Seno et al., Anal. Sci. 24, 505 (2008) DOI PubMed. Synthetic applications: M. K. Dhaon et al., J. Org. Chem. 47, 1962 (1982) DOI; G.-J. Ho et al., ibid. 60, 3569 (1995) DOI; D. S. Bose, K. S. Sunder, Synth. Commun. 29, 4235 (1999) DOI; H. Sai et al., Synthesis 2003, 201 DOI. Cross-linking applications: J. M. Lee et al., J. Mater. Sci. Mater. Med. 7, 531 (1996) DOI; H. M. Powell, S. T. Boyce, Biomaterials 27, 5821 (2006) DOI PubMed. Brief description and review of synthetic uses: R. S. Pottorf, P. Szeto in Encyclopedia of Reagents for Organic Synthesis 4, L. A. Paquette, Ed. (John Wiley & Sons, New York, 1995) pp 2430-2432.

Chemical structure

Properties

Oil. Corrosive. bp0.60 53-54°; bp0.27 47-48°. nD25 1.4582; nD22 1.4594. pKa1 3.1; pKa2 11.1. Sol in ether.

Derivative

Hydrochloride.

Nomenclature

CAS number: 25952-53-8
C8H17N3.HCl; mol wt 191.70.
C 50.12%, H 9.46%, N 21.92%, Cl 18.49%.

Properties

White, smooth, powdery crystals from dichloromethane-ether, mp 113.5-114.5°. Irritant. Sol in water, dichloromethane, DMF, THF.

Derivative

Methiodide.

Nomenclature

CAS number: 22572-40-3
[3-[(Ethylimidocarbonyl)amino]propyl]trimethylammonium iodide.
C8H17N3.CH3I; mol wt 297.18.
C 36.37%, H 6.78%, N 14.14%, I 42.70%.

Properties

White solid from ethyl acetate-chloroform, mp 106.5-107.5°. Irritant.

Use

Reagent in synthetic organic chemistry. In the cross-linking of tissue derived biomaterials and of proteins to nucleic acids. In DNA labeling and in the prepn of immunoconjugates.