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Sigma-Aldrich

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

for synthesis

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Synonym(s):
N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride
Empirical Formula (Hill Notation):
C8H17N3 · xHCl
CAS Number:
25952-53-8
Molecular Weight:
155.24 (free base basis)
MDL number:
MFCD00012503
EC Index Number:
247-361-2

Quality Level

200

form

solid

reaction suitability

reaction type: Coupling Reactions

mp

110-115 °C

application(s)

peptide synthesis

storage temp.

−20°C (−15°C to −25°C)

InChI

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

InChI key

FDXPUDRRFDHONO-UHFFFAOYSA-N

Related Categories

General description

N-(3-Dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride, also known as EDAC HCl or WSC, is a water-soluble condensing reagent. EDAC HCl is generally used to couple carboxylic acids with amines to form amides. The by-product urea is water-soluble and can be removed from immiscible reaction milieux by extraction with water. It is principally utilized in solution-phase peptide synthesis and as a zero-length crosslinker for protein modification.

Application

N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC hydrochloride) can be used as:
  • A water-soluble carbodiimide to facilitate peptide coupling reactions in alcohols.
  • A coupling agent along with HOBt to synthesize poly(glutamic acid) (PGA) polypeptides for the creation of non-fouling polypeptides that could be useful in a variety of biomedical applications.
  • A coupling reagent for the efficient synthesis of teriflunomide at the industrial scale.

Signal Word

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 Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Investigation of nonfouling polypeptides of poly (glutamic acid) with lysine side chains synthesized by EDCHCl/HOBt chemistry
Yang Q, et al.
Journal of Biomaterials Science. Polymer Edition, 25, 1717-1729 (2014)
EDC-promoted one-step synthesis of teriflunomide at the industrial scale
Wang L, et al.
Reaction Chemistry & Engineering, 2493-2496 (2022)
Effects of amounts of additives on peptide coupling mediated by a water-soluble carbodiimide in alcohols
Nozaki S
The Journal of Peptide Research, 54, 162-167 (1999)

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