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1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

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1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride Basic information
Product Name:1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride
Product Categories:Aliphatics;straight chain compounds;Peptide Coupling Reagents;Biochemistry;heteroXlink;EDC;Condensation & Active Esterification;Coupling Reactions (Peptide Synthesis);Peptide Synthesis;Reagents for Oligosaccharide Synthesis;Synthetic Organic Chemistry;Peptide;Amine;Zero-Length Crosslinker;peptides
Mol File:25952-53-8.mol
1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride Structure
1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride Chemical Properties
Melting point 110-115 °C(lit.)
density 0.877 g/mL at 20 °C(lit.)
vapor pressure 0.002Pa at 20℃
refractive index n20/D 1.461
storage temp. -20°C
solubility H2O: soluble1 gm/10 ml, clear to very slightly hazy, colorless to very faintly yellow
form Crystalline Powder
color White to off-white
Water Solubility Soluble
Sensitive Hygroscopic
BRN 5764110
Stability:Stable, but sensitive to moisture. Incompatible with strong acids, strong oxidizing agents, moisture.
LogP-2.98 at 25℃
CAS DataBase Reference25952-53-8(CAS DataBase Reference)
EPA Substance Registry System1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride (25952-53-8)
Safety Information
Hazard Codes C,Xi
Risk Statements 34-36/37/38-41-37/38-20/21/22
Safety Statements 26-36/37/39-45-37/39-36
RIDADR UN 2735 8/PG 3
WGK Germany 3
RTECS FF2200000
Hazard Note Irritant
HS Code 29252000
ToxicityLD50 intravenous in mouse: 56mg/kg
MSDS Information
EDAC.HCl English
SigmaAldrich English
ALFA English
1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride Usage And Synthesis
Chemical Properties1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride is a white crystalline powder, easily deliquescent, soluble in water >20g/100ml, soluble in ethanol, used as an activating reagent for carboxyl groups in amide synthesis, also used for activating phosphate groups, cross-linking of proteins and nucleic acids, and the production of immunocouplers. EDC-HCl is used in the pH range of 4.0-6.0 and is often used in conjunction with N-Hydroxysuccinimide (NHS) or N-Hydroxysulfosuccinimide sodium salt to improve coupling efficiency.
Uses1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride is water-soluble carbodiimide, widely used for peptide coupling.
Uses1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride is used as a carboxyl activating agent. It plays a vital role for immobilization of large biomolecules in association with N-hydroxysuccinimide. It is also used in the acylation of phosphoranes.
General DescriptionWater-soluble derivative of carbodiimide useful for conjugating haptens to proteins and polypeptides. Used to modify NMDA receptors and as a condensing agent in peptide synthesis. The major advantage of EDAC coupling is the easy removal of excess reagent and the corresponding urea by washing with dilute acid or water. Carbodiimides catalyze the formation of amide bonds, carboxylic acids, and amines by activating the carboxylate to form an O-acylurea. This intermediate can be attacked by an amine directly to form an amide. EDAC is released as a soluble urea derivative.
Flammability and ExplosibilityFlammable
Biochem/physiol Actions1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride is a water soluble condensing reagent. EDAC is generally utilized as a carboxyl activating agent for amide bonding with primary amines. Additionally, it reacts with phosphate groups. It has been utilized in peptide synthesis, crosslinking proteins to nucleic acids as well as preparation of immunoconjugates.
Synthesis1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride can be used for the synthesis of amides. It is used as a coupling agent in the synthesis of esters from carboxylic acids using dimethylaminopyridine as the catalyst. 
Purification MethodsIt is an excellent H2O-soluble peptide coupling reagent. It is purified by dissolving (ca 1g) in CH2Cl2 (10mL) at room temperature and then add dry Et2O (~110mL) dropwise and the crystals that separate are collected, washed with dry Et2O, recrystallised from CH2Cl2/Et2O and dried in a vacuum over P2O5. It is important to work in a dry atmosphere or work rapidly and then dry the solid as soon as possible. The material is moderately hygroscopic, but once it becomes wet it reacts slowly with H2O. Store it away from moisture at -20o to slow down the hydrolysis process. The free base has b 47-48o/0.27mm, 53-54o/0.6mm, n 1.4582. The methiodide is recrystallised from CHCl3/EtOAc, the crystals are filtered off, washed with dry Et2O, recrystallised from CHCl3/Et2O, and dried in vacuo over P2O5, m 93-95o, 94-95o. [Sheehan et al. J Am Chem Soc 87 2492 1965, Sheehan & Cruickshank Org Synth Coll Vol V 555 1973.] § A polymer bound version is commercially available.
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