1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide
[CAS# 1892-57-5]

Identification

• Classification: Chemical reagent >> Organic reagent >> Imide
• Name: 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide
• Synonyms: N-(3-Dimethylaminopropyl)-N'-ethylcarbodiimide; N-Ethyl-N'-(3-dimethylaminopropyl)carbodiimide
• Molecular Formula: C₈H₁₇N₃
• Molecular Weight: 155.24
• CAS Registry Number: 1892-57-5
• EC Number: 217-579-2
• SMILES: CCN=C=NCCCN(C)C

Properties

• Density: 0.885 g/mL
• Melting point: 100-115 ºC
• Boiling point: 66-69 ºC
• Refractive index: 1.461

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07;GHS08;GHS09 Danger
• Hazard Statements: H302-H311-H314-H373-H410
• Precautionary Statements: P260-P264-P270-P272-P273-P280-P301+P312+P330-P302+P352+P312-P314-P333+P313-P391-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Acute toxicity	Acute Tox.	3	H311
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Skin irritation	Skin Irrit.	2	H315
Respiratory sensitization	Resp. Sens.	1	H334
Serious eye damage	Eye Dam.	1	H318
Skin corrosion	Skin Corr.	1C	H314

• Transport Information: UN 2735

Discovory and Applicatios

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide, commonly known as EDC or EDCI, is a widely used carbodiimide reagent in organic synthesis. Its main application is the formation of amide bonds and it is a key reagent in peptide synthesis and other organic transformations.

The use of carbodiimides in organic synthesis dates back to the mid-20th century. EDC was first synthesized in the 1960s and introduced as a coupling reagent. It was developed to meet the need for efficient and versatile reagents that can promote the formation of amide bonds without the need for harsh conditions or additional catalysts. EDC stands out among carbodiimides because its solubility in water and organic solvents makes it highly versatile in a variety of synthetic applications.

The chemical formula of EDC is C₈H₁₇N₃, and its structure consists of a carbodiimide functional group (-N=C=N-) and 3-dimethylaminopropyl and ethyl groups. This structure gives EDC a unique reactivity that allows it to act as an efficient dehydrating agent. In aqueous solution, EDC is often used in combination with N-hydroxysuccinimide (NHS) or hydroxybenzotriazole (HOBt) to enhance its coupling efficiency.

One of the most important applications of EDC is in peptide synthesis, where it facilitates the formation of peptide bonds between amino acids. EDC activates carboxyl groups, making them more susceptible to nucleophilic attack by amines, resulting in the formation of amide bonds. This process is essential for the synthesis of peptides and proteins, both in research and industrial settings.

In a typical peptide synthesis protocol, EDC is used in combination with NHS or HOBt to form an active ester intermediate. This intermediate then reacts with amines to generate the desired peptide bond. The use of EDC in peptide synthesis is advantageous due to its high efficiency, mild reaction conditions, and compatibility with a wide range of amino acids and protecting groups.

In addition to peptide synthesis, EDC is also widely used in bioconjugation, a process involving the attachment of biomolecules such as proteins, nucleic acids, and small molecules. EDC-mediated coupling reactions are used to attach biomolecules to surfaces, create protein-protein or protein-DNA conjugates, and immobilize enzymes. These applications are critical for the development of biosensors, diagnostic assays, and therapeutic agents.

EDC offers several advantages as a coupling agent: Unlike many other carbodiimides, EDC is soluble in water, allowing reactions to be performed under aqueous conditions. EDC effectively activates the carboxyl group, allowing for fast and efficient coupling reactions. Reactions using EDC are typically performed under mild conditions, preserving the integrity of sensitive biomolecules. EDC is compatible with a wide range of functional groups, making it suitable for different synthetic applications.

EDC should be handled with care as it can be irritating to the skin, eyes, and respiratory system. Appropriate protective equipment, such as gloves and goggles, should be worn when handling the reagent. EDC is also hygroscopic and should be stored in a dry, cool place to prevent degradation.

References

2003. Immunosensor for detection of Legionella pneumophila using surface plasmon resonance. Biosensors and Bioelectronics, .
DOI: 10.1016/s0956-5663(03)00032-0

2020. A Tissue Chamber Chip for Assessing Nanoparticle Mobility in the Extravascular Space. Biomedical Micro-Nanotechnologies Toward Translation, .
DOI: 10.1007/978-1-0716-0187-7_20