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

CAS No.
25952-53-8
Chemical Name:
1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride
Synonyms
EDCI;EDC.HCl;EDAC;EDARAVONE;WSC;1-ETHYL-3-(3-DIMETHYLAMINOPROPYL) CARBODIIMIDE;WSCI;WSCD;1-Ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride;EDC.HCI
CBNumber:
CB7403031
Molecular Formula:
C8H18ClN3
Molecular Weight:
191.7
MDL Number:
MFCD00044916
MOL File:
25952-53-8.mol
Last updated:2024-01-10 17:27:35

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride 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.
InChIKey FPQQSJJWHUJYPU-UHFFFAOYSA-N
LogP -2.98 at 25℃
CAS DataBase Reference 25952-53-8(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII 19W5TL0WJ4
EPA Substance Registry System 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride (25952-53-8)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictogramsGHS hazard pictograms
GHS06,GHS08,GHS09
Signal word  Danger
Hazard statements  H302-H311-H315-H317-H373-H410
Precautionary statements  P260-P273-P280-P301+P312-P302+P352+P312-P314
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
1-3-10
Hazard Note  Irritant
TSCA  Y
HS Code  29252000
Toxicity LD50 intravenous in mouse: 56mg/kg
NFPA 704
1
3 1

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride price More Price(76)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich E6383 N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride crystalline 25952-53-8 25G $570 2024-03-01 Buy
Sigma-Aldrich 8.00907 N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride forsynthesis 25952-53-8 500mg $43.9 2024-03-01 Buy
Sigma-Aldrich 8.00907 N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride forsynthesis 25952-53-8 1g $56.6 2024-03-01 Buy
Sigma-Aldrich 8.00907 N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride forsynthesis 25952-53-8 5G $165 2024-03-01 Buy
Sigma-Aldrich 8.00907 N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride forsynthesis 25952-53-8 25g $343 2024-03-01 Buy
Product number Packaging Price Buy
E6383 25G $570 Buy
8.00907 500mg $43.9 Buy
8.00907 1g $56.6 Buy
8.00907 5G $165 Buy
8.00907 25g $343 Buy

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride Chemical Properties,Uses,Production

Chemical Properties

EDC-HCl, or 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, is a white crystalline powder that easily deliquescent and can dissolve in both water and ethanol. It is commonly used as an activating reagent in amide synthesis to activate carboxyl groups. It can also activate phosphate groups, cross-link proteins and nucleic acids, and produce immunocouplers. EDC-HCl is commonly applied 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.

Uses

1-(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.

Application

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride is water-soluble carbodiimide, widely used for peptide coupling.
N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride has been used for the formation of FND (fluorescent nanodiamonds)-transferrin bioconjugates.
It has been used for crosslinking polyethylenimine to gold particles.
It has been used as a carbodiimide linkage agent for coating of carboxylated polystyrene beads with biotinylated BSA (bovine serum albumin).

General Description

EDC hydrochloride is a water-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 Explosibility

Flammable

Biochem/physiol Actions

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride(25952-53-8) 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.

Mechanism of action

Carboxyl group activation with EDC. xHCl proceeds similarly to other carbodiimide couplings. The reaction of a carboxylic acid and the carbodiimide forms an O-acylisourea intermediate. The O-acylisourea is a highly reactive species that readily reacts with amines, peptide coupling additives, or reducing agents. EDC. HCl is transformed into the corresponding urea during coupling reactions. It has the advantage over DCU in that it can be removed from the reaction mixture by extraction or be washed out from solid phase synthesis applications. However, the O-acylisourea can rearrange irreversibly to an N-acyl urea and racemise the α-carbon of the amino acid via the formation of an oxazol-4(5H)-one [azlactone]. N-Acylurea formation and racemisation may be reduced by using intermediate nucleophiles, which convert the O-acylurea to an activated ester containing the nucleophile. The mechanism of amide bond formation applies both to EDC and EDC.HCl. The differences are that the free base can be applied as a bifunctional reagent: a coupling agent (carbodiimide) and a base (dimethylamino). At the same time, the HCl salt can form an O-acylisourea cyclic intermediate.

Synthesis

1-(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.
Preparation method of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride(CN104193654A)

Purification Methods

It 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.

1892-57-5
25952-53-8
Synthesis of 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride from 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide
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1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride pictures 2024-03-19 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride
25952-53-8
US $0.00 / kg 100g 99% 100mt Jinan Finer Chemical Co., Ltd
EDC hydrochloride pictures 2024-02-23 EDC hydrochloride
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US $104.00 / kg 1kg 0.99 100kg Shanghai UCHEM Inc.
1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride pictures 2024-01-20 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride
25952-53-8
US $9.90-9.90 / g 10g 99.99%HPLC.USP42——Powder、Oil、Pills、Capsules、Tablets,Customized packaging 100KG Wuhan Biocar Pharmacy Co., Ltd.
edc(reagent) WATER-SOLUBLE CARBODIIMIDE 1-ETHYL-3-(3-DIMETHYLAMINOPROPYL)- & N-(DIMETHYLAMINOPROPYL)-N'-ETHYLCARBO- DI IMIDE HCL 1-(3-(DIMETHYLAMINO)PROPYL)-3-ETHYL-CARBODIIMIDE HYDROCHLORIDE, 98+% 1-(3-Dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (EDC) EDC (WSC-HCl) WS.HCl 1-ethyl-3-(3-Dimethylaminopropyl) carbodiimide HCl(EDC HCl) eDC [1-(3-Dimethylaminopropyl)-3-ethyl-carbodiimide] eDC HCl [1-ethyl-3-(3-Dimethylaminopropyl) carbodiimide HCl] 1-ETHYL-3-(3-DIMETHYLAMINOPROPYL)-*CARBO DIIMIDE HYD 1-ETHYL-3-(3-DIMETHYLAMINOPROPYL)*CARBOD IIMIDE HYDR EDAC hydrochloride, EDC hydrochloride 1-Ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride, anhydrous 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Hydrochloride [Coupling Agent for Peptides Synthesis] N-(3-Dimethylaminopropyl)-Nμ-ethylcarbodiimide hydrochloride (EDC) 98% Carbodiimide, (3-dimethylaminopropyl)ethyl-, monohydrochloride N-(3-Dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride ,99% Edccl 1-[3-(Dimethylamino)propyl]-3-ethylcarbodiimide·hydrochloric acid 1-Ethyl-3-[3-(dimethylamino)propyl]carbodiimide·hydrochloric acid N-[3-(Dimethylamino)propyl]-N'-ethylcarbodiimide·hydrochloric acid N-Ethyl-N'-[3-(dimethylamino)propyl]carbodiimide·hydrochloric acid EDAC hydrochloride (N-(3-Dimethylaminopropyl)-N'-ethylcarbodiimi 1-(3-DiMethylaMinopropyl)-3-ethylcarbodiiMide hydrochloride CAS: 25952-53-8 (3-DiMethylaMino-propyl)-ethyl-carbodiiMide Hydrochloride, EDC HCl, EDAC, EDCI, Water Soluble CarbodiiMide. 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Hydrochloride EDC EDAC EDCI EDAC · HCl, N-(3-DiMethylaMinopropyl)-N'-ethylcarbodiiMide · HCl, Water-soluble CarbodiiMide, WSC, EDC · HCl EDCHC1/EDACHC1 N-(3-DIMETHYLAMINOPROPYL)-N'-ETHYLCARBOD -(3-DiMethylaMinopropyl)-3-ethylcarbodiiMide hydrochloride 1-(3-DiMethylaMinopropyl)-3-ethylcabodiiMide HCl 3-(ethyliMinoMethyleneaMino)-N,N-diMethylpropan-1-aMine EDC hydrochloride, N,N-Dimethyl-3-{[(ethylimino)methylidene]amino}propylamine hydrochloride 1-[3-(DIMETHYLAMINO)PROPYL]-3-ETHYLCARBODIIMIDE(EDC.HCL) 1ETHYL33DIMETHYLAMINOPROPYLCARBODIIMIDEHYDROCHLOR 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide Hydrochloride (EDCI) N-ETHYL-N''-(3-DIMETHYLAMINOPROPYL)CARBODIIMIDE HYDROCHLORIDE, EDAC, WSC N-(3-DIETHYLAMINOPROPYL) -N -ETHYLCARBODIIMIDE HYD N-(3-DIETHYLAMINOPROPYL)-N -ETHYLCARBODIIMIDE HYDR 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride N'-(ethylcarbonimidoyl)-N,N-dimethylpropane-1,3-diamine monohydrochloride N-Ethyl-N'-(3-dimethylaminopropyl)carbodiimide hydrochloride (E)-3-(ETHYLDIAZENYL)-N,N-DIMETHYLPROPAN-1-AMINE HYDROCHLORIDE EDAC HYDROCHLORIDE (N-(3-DIMETHYLAMINOPROPYL)-N''-ETHYLCARBODIIMIDE HYDROCHLORIDE) EDC.HCL 1-[3-(DIMETHYLAMINO)PROPYL]-3-ETHYLCARBODIIMIDE HYDROCHLORIDE N3-(ETHYLCARBONIMIDOYL)-N1,N1-DIMETHYL-1,3-PROPANEDIAMINE HYDROCHLORIDE N-(3-Dimethylaminopropyl)-N''-ethylcar ETHYL-3-(3-DIMETHYLAMINOPROPYL)CARBODIIMIDE HCL 1-Ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride / EDAC / EDCI 1-Ethyl-3-(3-Dimethylaminopropyl)carbodiiamide Hydrochloride 1-Ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (EDC-HCl) N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride,N-Ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride, EDAC, EDC hydrochloride, WSC hydrochloride N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride commercial grade, powder EDAC.HC N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide h N-[3-(Dimethylamino)prop-1-yl]-N'-ethylcarbodiimide hydrochloride