1-ethyl-3- (3-dimethylaminopropyl) carbodiimide

Structural formula
General
Surname	1-ethyl-3- (3-dimethylaminopropyl) carbodiimide
other names	3- (Ethyliminomethylidenamino) - N , N -dimethyl-propan-1-amine ( IUPAC ) ; 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide; EDC; EDAC; EDCI; WSCD;
Molecular formula	C 8 H 17 N 3
Brief description	clear liquid; colorless to yellowish solid (hydrochloride);
External identifiers / databases
EC number	217-579-2
ECHA InfoCard	100,015,982
PubChem	15908
ChemSpider	15119
Wikidata	Q161622
properties
Molar mass	155.24 g mol −1
Physical state	liquid; solid (hydrochloride);
density	0.88 g cm −3
Melting point	111–113 ° C (hydrochloride);
boiling point	47-48 ° C (36 Pa )
solubility	good at dichloromethane , DMF and THF ; soluble in water (hydrochloride);
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 314
	P: 280-305 + 351 + 338-310
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

1-Ethyl-3- (3-dimethylaminopropyl) carbodiimide ( EDC, EDCI or EDAC ) is a reactive organic compound from the group of carbodiimides , which is often used in synthetic chemistry . Due to the better handling, the hydrochloride is usually used instead of the free base .

Presentation and extraction

The synthesis can take place in two reaction steps. In the first step, ethyl isocyanate is reacted with N , N -dimethyl-1,3-diaminopropane . The resulting urea derivative is then dehydrated to the target compound in the second step.

properties

Like most carbodiimides , the substance hydrolyzes in aqueous solution; in the acidic pH range this happens faster. The connection is thermally unstable. A DSC measurement shows a strongly exothermic decomposition reaction from 120 ° C with a heat release of −549 kJ kg ⁻¹ or −105.2 kJ mol ⁻¹ .

use

EDC is often for the synthesis of carboxamides and in biochemistry for chemical cross-linking ( cross-linking ) of proteins used. In contrast to dicyclohexylcarbodiimide , the urea formed in carboxamide syntheses can easily be separated off.

safety instructions

The free base irritates the eyes, mucous membranes and skin and acts as a contact allergen . When burned, poisonous gases such as carbon monoxide and nitrogen oxides can be produced.

Individual evidence

↑ ^a ^b ^c ^d Data sheet N- (3-Dimethylaminopropyl) -N′-ethylcarbodiimide from Sigma-Aldrich , accessed on February 7, 2020 ( PDF ).
↑ ^a ^b Data sheet 1-Ethyl-3- (3-dimethylaminopropyl) carbodiimide (PDF) from Merck , accessed on January 19, 2011.
↑ External identifiers of or database links to N '- (Ethylcarbonimidoyl) -N, N-dimethylpropane-1,3-diamine hydrochloride : CAS number: 25952-53-8, EC number: 247-361-2, ECHA InfoCard: 100.043.041 , PubChem : 2723939 , ChemSpider : 2006116 , Wikidata : Q55444948 .
↑ RS Pottorf: 1-Ethyl-3- (3'-dimethylaminopropyl) carbodiimide hydrochloride. In: Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons, 2001, doi: 10.1002 / 047084289X.re062
↑ ^a ^b ^c ^d Peter Wipf: Handbook of Reagents for Organic Synthesis. Wiley, 2005, ISBN 0-470-86298-X .
↑ J. Sheehan, P. Cruickshank, G. Boshart: A Convenient Synthesis of Water-Soluble Carbodiimides. In: J. Org. Chem. 26, (1961) 2525, doi: 10.1021 / jo01351a600 .
↑ Nadia Wrobel, Manfred Schinkinger, Vladimir M. Mirsky: A Novel Ultraviolet Assay for Testing Side Reactions of Carbodiimides . In: Analytical Biochemistry . tape 305 , no. 2 , p. 135-138 , doi : 10.1006 / abio.2002.5646 ( elsevier.com [accessed May 12, 2017]).
↑ Sperry, JB; Minteer, CJ; Tao, J .; Johnson, R .; Duzguner, R .; Hawksworth, M .; Oke, S .; Richardson, PF; Barnhart, R .; Bill, DR; Giusto, RA; Weaver, JD: Thermal Stability Assessment of Peptide Coupling Reagents Commonly Used in Pharmaceutical Manufacturing in Org. Process Res. Dev. 22 (2018) 1262-1275, doi : 10.1021 / acs.oprd.8b00193 .
↑ D. Schulz, A. Sinz: Chemical cross-linking and mass spectrometry for the structural and functional characterization of proteins. In: Biospectrum. Vol. 10, No. 1, 2004, pp. 45-48. (PDF)

[SigmaAldrich-1] Data sheet N- (3-Dimethylaminopropyl) -N′-ethylcarbodiimide from Sigma-Aldrich , accessed on February 7, 2020 ( PDF ).

[merck-2] Data sheet 1-Ethyl-3- (3-dimethylaminopropyl) carbodiimide (PDF) from Merck , accessed on January 19, 2011.

[3] External identifiers of or database links to N '- (Ethylcarbonimidoyl) -N, N-dimethylpropane-1,3-diamine hydrochloride : CAS number: 25952-53-8, EC number: 247-361-2, ECHA InfoCard: 100.043.041 , PubChem : 2723939 , ChemSpider : 2006116 , Wikidata : Q55444948 .

[Pottorf-4] RS Pottorf: 1-Ethyl-3- (3'-dimethylaminopropyl) carbodiimide hydrochloride. In: Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons, 2001, doi: 10.1002 / 047084289X.re062

[wipf-5] Peter Wipf: Handbook of Reagents for Organic Synthesis. Wiley, 2005, ISBN 0-470-86298-X .

[6] J. Sheehan, P. Cruickshank, G. Boshart: A Convenient Synthesis of Water-Soluble Carbodiimides. In: J. Org. Chem. 26, (1961) 2525, doi: 10.1021 / jo01351a600 .

[7] Nadia Wrobel, Manfred Schinkinger, Vladimir M. Mirsky: A Novel Ultraviolet Assay for Testing Side Reactions of Carbodiimides . In: Analytical Biochemistry . tape 305 , no. 2 , p. 135-138 , doi : 10.1006 / abio.2002.5646 ( elsevier.com [accessed May 12, 2017]).

[Sperry-8] Sperry, JB; Minteer, CJ; Tao, J .; Johnson, R .; Duzguner, R .; Hawksworth, M .; Oke, S .; Richardson, PF; Barnhart, R .; Bill, DR; Giusto, RA; Weaver, JD: Thermal Stability Assessment of Peptide Coupling Reagents Commonly Used in Pharmaceutical Manufacturing in Org. Process Res. Dev. 22 (2018) 1262-1275, doi : 10.1021 / acs.oprd.8b00193 .

[9] D. Schulz, A. Sinz: Chemical cross-linking and mass spectrometry for the structural and functional characterization of proteins. In: Biospectrum. Vol. 10, No. 1, 2004, pp. 45-48. (PDF)