1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide
EDCI · EDAC · 1-ETHYL-3-(3-DIMETHYLAMINOPROPYL) CARBODIIMIDE · WSCI · WSCD · N1-((EthyliMino)Methylene)-N3,N3-diMethylpropane-1,3-diaMine · ({[3-(dimethylamino)propyl]imino}methylidene)(ethyl)amine · 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide
Identifiers & Physical Properties
| CAS No. | 1892-57-5 |
|---|---|
| Molecular formula | C8H17N3 |
| Average molar mass | 155.24 g/mol |
| Monoisotopic mass | 155.14224754 g/mol |
| SMILES | CCN=C=NCCCN(C)C |
| InChIKey | LMDZBCPBFSXMTL-UHFFFAOYSA-N |
| PubChem CID | 15908 |
| ChEMBL | CHEMBL1397523 |
| EC No. | 217-579-2 |
| DTXSID | DTXSID60865258 |
Chemical & Physical Properties
| XLogP | 1.9 |
|---|---|
| Topological polar surface area | 28 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 3 |
| Rotatable bonds | 5 |
| Heavy atoms | 11 |
| Formal charge | 0 |
| Complexity | 134 |
| Chemical classes | Other Uses -> Biochemical Research |
| Physical Description | Liquid[Merck Index] Colorless to pale yellow liquid[Alfa Aesar MSDS] |
| Boiling point | 66-68°C/1mm |
| Density | 0.877 g/mL at 20 °C (lit.) |
| Refractive index | n20/D 1.461 |
| Flash point | 66-68°C/1mm |
| Storage conditions | -20°C |
| Solubility | ChloroformSoluble in water. |
| pKa (acidity coefficient) | 9.52±0.28(Predicted) |
| Physical state | Liquid |
| Specific gravity | 0.885 |
| Color | Colorless to slightly yellow |
| Sensitivity | Air Sensitive |
| BRN | 507429 |
| Major applications | 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) |
| FDA UNII | RJ5OZG6I4A |
| NIST Chemistry Reference | 1,3-Propanediamine, n'-(ethylcarbonimidoyl)-n,n-dimethyl-(1892-57-5) |
| EPA Substance Registry System | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl- (1892-57-5) |
| UNSPSC Code | 12352116 |
| NACRES | NA.22 |
| GHS pictogram | GHS06,GHS08,GHS09 |
| Signal word | Danger |
| GHS hazard statements | H302-H311-H315-H317-H373-H410 |
| GHS precautionary statements | P260-P273-P280-P301+P312-P302+P352+P312-P314 |
| Target organs | Stomach,large intestine,lymph node |
| Personal protective equipment (PPE) | Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter |
| Hazard symbols | C |
| Risk statements (R) | 34 |
| Safety statements (S) | 26-36/37/39-45 |
| UN transport number | UN 2735 8/PG 3 |
| Water hazard class (WGK) | 3 |
| F | 1-3-10 |
| TSCA inventory status | TSCA listed |
| Hazard class | 8Acute Tox. 3 DermalAcute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Eye Dam. 1Skin Corr. 1ASkin Sens. 1ASTOT RE 2 Oral |
| Packing group | III |
| Customs code | 29252900 |
| Storage class | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
Safety & Regulations
| GHS classification | DangerH302 (32.3%): Harmful if swallowed [Warning Acute toxicity, oral]P233, P260, P261, P262, P264, P270, P271, P272, P273, P280, P284, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P319, P321, P330, P332+P317, P333+P317, P342+P316, P361+P364, P362+P364, P363, P391, P403, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 62 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazards summary | Corrosive[Merck Index] Causes burns[Alfa Aesar MSDS] |
| Hazard Classes and Categories | Acute Tox. 4 (32.3%) |
| Adverse effects | Dermatotoxin - Skin burns. |
| F | 1-3-10 |
| Personal protective equipment (PPE) | Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| UN transport number | UN 2735 8/PG 3 |
| Customs code | 29252900 |
| Risk statements (R) | 34 |
| Signal word | Danger |
| GHS pictogram | GHS06,GHS08,GHS09 |
| Hazard symbols | C |
| Safety statements (S) | 26-36/37/39-45 |
| Hazard class | 8Acute Tox. 3 DermalAcute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Eye Dam. 1Skin Corr. 1ASkin Sens. 1ASTOT RE 2 Oral |
| Storage class | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
| Packing group | III |
| Target organs | Stomach,large intestine,lymph node |
| GHS hazard statements | H302-H311-H315-H317-H373-H410 |
| GHS precautionary statements | P260-P273-P280-P301+P312-P302+P352+P312-P314 |
Applications & Uses
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].
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.