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

chemical compound

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Record originEnglish Wikipedia
Text licenseCC BY-SA 4.0
Source revisionNov 17, 2025
Entity authorityQ161622 ↗
Source-derived summary

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC, EDAC or EDCI) is a water-soluble carbodiimide usually handled as the hydrochloride, which is a white solid.

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. While other carbodiimides like dicyclohexylcarbodiimide (DCC) or diisopropylcarbodiimide (DIC) are also employed for this purpose, EDC has the advantage that the urea byproduct formed (often challenging to remove in the case of DCC or DIC) can be washed away from the amide product using dilute acid. Additionally, EDC can also be used to activate phosphate groups in order to form phosphomonoesters 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. Recent work has also used EDC to assess the structure state of uracil nucleobases in RNA.

Preparation

EDC is commercially available. It may be prepared by coupling ethyl isocyanate to N,N-dimethylpropane-1,3-diamine to give a urea, followed by a dehydration reaction mediated by TsCl and TEA:

Mechanism

EDC couples primary amines, and other nucleophiles, to carboxylic acids by creating an activated ester leaving group. First, the carbonyl of the acid attacks the carbodiimide of EDC, and there is a subsequent proton transfer.

Editorial summary

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Editorial reviewUseful for establishing the present vocabulary of the subject while preserving a route back to the evidence on which that vocabulary rests. The current 226-word lead offers orientation but no explicit four-digit date, so chronology should not be assumed. The selected authority fields contribute no independent date. The account is most persuasive where 1-Ethyl-3-, 3-dimethylaminopropyl and carbodiimide can be independently traced.
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The date and method of observation matter as much as the stated conclusion, especially where classification or consensus has changed. The source revision retrieved here is dated Nov 17, 2025. The linked authority identifier is Q161622. None of the 0 selected statements returned an explicit reference.

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This entry incorporates text from “1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide” on English Wikipedia. Contributors are listed in the page history. Text is available under the Creative Commons Attribution-ShareAlike 4.0 License. Selected authority identifiers and statements are retrieved from Wikidata under CC0; their references and qualifiers remain part of the verification path.