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1892-57-5

1892-57-5 Structure

1892-57-5 Structure
IdentificationMore
[Name]

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide
[CAS]

1892-57-5
[Synonyms]

1-(3-DIMETHYLAMINOPROPYL)-3-ETHYLCARBODIIMIDE
1-ETHYL-3-(3-DIMETHYLAMINOPROPYL) CARBODIIMIDE
EDAC
EDC
EDCI
N-(3-DIMETHYLAMINOPROPYL)-N'-ETHYLCARBODIIMIDE
N-ETHYL-N'-(3-DIMETHYLAMINOPROPYL)CARBODIIMIDE
WATER-SOLUBLE CARBODIIMIDE
WSCD
WSCI
[3-(Dimethylamino)propyl]ethylcarbodiimide
ethyldimethylaminopropylcarbodiimide
n’-(ethylcarbonimidoyl)-n,n-dimethyl-3-propanediamine
N3-Ethyliminomethylene-N1,N1-dimethylpropane-1,3-diamine
1-(3-dimethylaminopropyl)-N?ethylcarbodiimide
N'-(ethylcarbonimidoyl)-N,N-dimethylpropane-1,3-diamine
EDC polymer-bound, N-Ethyl-Nμ-(3-dimethylaminopropyl)carbodiimide polymer-bound, N-(3-Dimethylaminopropyl)-Nμ-ethylcarbodiimide polymer-bound
EDC, WSC, N-Ethyl-Nμ-(3-dimethylaminopropyl)carbodiimide
3-[(Ethylcarbonimidoyl)amino]-N,N-dimethyl-1-propanamine
WSC【Dotite】
[EINECS(EC#)]

217-579-2
[Molecular Formula]

C8H17N3
[MDL Number]

MFCD00044916
[Molecular Weight]

155.24
[MOL File]

1892-57-5.mol
Chemical PropertiesBack Directory
[Boiling point ]

66-68°C/1mm
[density ]

0.877 g/mL at 20 °C(lit.)
[refractive index ]

n20/D 1.461
[Fp ]

66-68°C/1mm
[storage temp. ]

−20°C
[solubility ]

Chloroform
[form ]

Liquid
[pka]

9.52±0.28(Predicted)
[color ]

Colorless to slightly yellow
[Specific Gravity]

0.885
[Water Solubility ]

Soluble in water.
[Sensitive ]

Air Sensitive
[BRN ]

507429
[Major Application]

peptide synthesis
[InChI]

1S/C8H17N3/c1-4-9-8-10-6-5-7-11(2)3/h4-7H2,1-3H3
[InChIKey]

LMDZBCPBFSXMTL-UHFFFAOYSA-N
[SMILES]

CCN=C=NCCCN(C)C
[CAS DataBase Reference]

1892-57-5(CAS DataBase Reference)
[NIST Chemistry Reference]

1,3-Propanediamine, n'-(ethylcarbonimidoyl)-n,n-dimethyl-(1892-57-5)
[EPA Substance Registry System]

1892-57-5(EPA Substance)
Safety DataBack Directory
[Symbol(GHS) ]

Skull and Crossbones (GHS06)Health Hazard (GHS08)Environment (GHS09)
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
[Risk Statements ]

R34:Causes burns.
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
[RIDADR ]

UN 2735 8/PG 3
[WGK Germany ]

3
[F ]

1-3-10
[TSCA ]

Yes
[HazardClass ]

8
[PackingGroup ]

III
[HS Code ]

29252900
[Storage Class]

6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials
[Hazard Classifications]

Acute Tox. 3 Dermal
Acute Tox. 4 Oral
Aquatic Acute 1
Aquatic Chronic 1
Eye Dam. 1
Skin Corr. 1A
Skin Sens. 1A
STOT RE 2 Oral
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Diethyl ether-->Dichloromethane-->Potassium carbonate-->Triethylamine-->Tosyl chloride-->3-Dimethylaminopropylamine-->Ethyl isocyanate
[Preparation Products]

N-Succinimidyl Methacrylate-->1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride
Hazard InformationBack Directory
[Description]

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide is a water-soluble carbodiimide available as hydrochloride salt. This compound is a carboxyl- and amine-reactive crosslinker that is water soluble and can activate carboxyl residues for their reaction with primary amines to form O-acylisourea as a reaction intermediate, which reacts with amide bonds to release isourea as a by-product. It can crosslink the carboxy-group of glutamate and aspartate to the side-chain primary amine of lysine and the amino group at the N-terminus. The crosslinker readily reacts at a pH range of 4.5–7.2 and only crosslinks the residues within their van der Waals distance. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide is also widely used in fabricating different nanosystems implemented in drug/protein delivery systems. It is mainly used for surface crosslinking/immobilization of drugs to increase stability against environmental changes, such as pH or temperature[1-2].
[Chemical Properties]

Clear light yellow liquid
[Uses]

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide is used as a carboxyl activating agent and activate phosphate groups in phospho mono and di esters. It is used in peptide synthesis, 3'-amino-3'-deoxyadenosine-5'-di- and triphosphates and in the preparation of antibodies like immunoconjugates. 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 Description]

N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide is commonly used in combination with N-hydroxysuccinimide (NHS) in carbodiimide coupling reaction to activate carboxyl group for coupling with amines to form amides.
[reaction suitability]

reaction type: Coupling Reactions
[Synthesis]

The production method of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide is to react with N, N'-dimethylpropanediamine and carbon disulfide as raw materials to prepare N, N'- Dimethylpropylthiourea. Then it is oxidized with ethyl chloroformate to obtain N, N'-dimethylpropyl isothiocyanate, which is then reacted with ethylamine and oxidized with sodium hypochlorite to obtain the product 1-(3-dimethylaminopropyl)-3- Ethylcarbodiimide.
1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide
[References]

[1] Manjula ;Mummadisetti et al.“Chapter Five-An approach to nearest neighbor analysis of pigment-protein complexes using chemical cross-linking in combination with mass spectrometry.” Methods in enzymology" Methods in Enzymology, 680 (2023) 139-162.
[2] Dmour, Isra and M. Taha. “Natural and semisynthetic polymers in pharmaceutical nanotechnology.”Organic Materials as Smart Nanocarriers for Drug Delivery (2018) 35-100.
Spectrum DetailBack Directory
[Spectrum Detail]

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide(1892-57-5)1HNMR
Well-known Reagent Company Product InformationBack Directory
[Alfa Aesar]

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide, 98%(1892-57-5)
[Sigma Aldrich]

1892-57-5(sigmaaldrich)
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