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E6383

Sigma-Aldrich

N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride

crystalline

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Synonym(s):
EDC, N-Ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride, EDAC, EDC hydrochloride, WSC hydrochloride
Empirical Formula (Hill Notation):
C8H17N3 · HCl
CAS Number:
Molecular Weight:
191.70
Beilstein/REAXYS Number:
5764110
EC Number:
MDL number:
PubChem Substance ID:

form

crystalline

Quality Level

reaction suitability

reagent type: cross-linking reagent
reaction type: Peptide Synthesis

mp

110-115 °C (lit.)

solubility

H2O: ≤100 mg/mL

application(s)

advanced drug delivery
general analytical

storage temp.

−20°C

SMILES string

Cl.CCN=C=NCCCN(C)C

InChI

1S/C8H17N3.ClH/c1-4-9-8-10-6-5-7-11(2)3;/h4-7H2,1-3H3;1H

InChI key

FPQQSJJWHUJYPU-UHFFFAOYSA-N

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This Item
E77500344903450
storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

Quality Level

200

Quality Level

300

Quality Level

200

Quality Level

200

mp

110-115 °C (lit.)

mp

110-115 °C (lit.)

mp

110-115 °C (lit.), 112-116 °C

mp

110-115 °C (lit.)

solubility

H2O: ≤100 mg/mL

solubility

H2O: ≤100 mg/mL

solubility

H2O: soluble 0.2 g/L

solubility

H2O: soluble 1 gm/10 ml, clear to very slightly hazy, colorless to very faintly yellow

reaction suitability

reagent type: cross-linking reagent
reaction type: Peptide Synthesis

reaction suitability

-

reaction suitability

-

reaction suitability

-

General description

1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride, commonly known as EDAC HCl, is a potent and widely employed water-soluble reagent in chemical and biochemical research due to its pivotal role in facilitating amide bond formation. In peptide synthesis, EDC HCl demonstrates efficiency by coupling amino acids through their carboxyl and amine groups, thereby forming peptide backbones. This capability is particularly valuable for creating peptides with specific sequences and functionalities.

Beyond peptides, EDC HCl extends its influence to the construction of immunogens, where it covalently attaches haptens (small immune-response eliciting molecules) to carrier proteins, playing an instrumental role in vaccine research. The versatility of EDAC HCl further unfolds in its ability to modify nucleic acids, allowing for the labeling of DNA and RNA through their 5′ phosphate groups. This facilitates the visualization, tracking, and analysis of these essential molecules, contributing to advancements in nucleic acid research.

Additionally, EDAC HCl serves as a biomolecule bridge by acting as a crosslinker, connecting amine-reactive NHS-esters of biomolecules to carboxyl groups. This technique proves valuable in protein conjugation, enabling the creation of hybrid molecules with novel properties and functions. The underlying mechanism of EDAC HCl involves its reaction with a carboxyl group, forming an unstable intermediate that actively seeks an amine partner. The delicate balance of this reaction underscores the importance of optimizing conditions for efficient conjugation. The assistance of N-hydroxysuccinimide (NHS) further enhances EDAC HCl′s capabilities, stabilizing the intermediate and enabling two-step conjugation procedures. This additional feature provides greater flexibility and control, particularly in dealing with complex biomolecules.

Application

N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride has been used:
  • for the immobilisation of trypsin onto self-assembled monolayers (SAMs)
  • as a component for the preparation of collagen matrices
  • for the preparation of phosphoethanolamine(PEt)-conjugated sepharose

Biochem/physiol Actions

Water soluble condensing reagent. EDAC is generally utilized as a carboxyl activating agent for amide bonding with primary amines. In addition, it will react with phosphate groups. EDAC has been used in peptide synthesis; crosslinking proteins to nucleic acids; and preparation of immunoconjugates as examples. Typically, EDAC is utilized in the pH range 4.0-6.0 without buffers. In particular, amine and carboxylate buffers should be avoided.

Features and Benefits

Versatile and adaptable for a wide variety of laboratory and research applications

Other Notes

For additional information on our range of Biochemicals, please complete this form.

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Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT RE 2 Oral

Storage Class

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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