Ethylisocyanacetat
Ethyl 2-isocyanoacetate · Isocyanoacetate · 2-Oxo-2-ethoxyethyl isocyanide · eica · HANSA ISN-0528 · eica cas2999-46-4 · BIO-FARMA BF001872 · IsocyanicAcidEster
Identifikatoren & physikalische Daten
| CAS No. | 2999-46-4 |
|---|---|
| Summenformel | C5H7NO2 |
| Durchschnittliche Molmasse | 113,11 g/mol |
| Monoisotopische Masse | 113,04767846 g/mol |
| SMILES | [C-]#[N+]CC(=O)OCC |
| InChIKey | FPULFENIJDPZBX-UHFFFAOYSA-N |
| PubChem CID | 533707 |
| EC No. | 221-077-9 |
| DTXSID | DTXSID20184078 |
| Lokaler Name | Ethylisocyanacetat |
Chemische & physikalische Eigenschaften
| XLogP | 0,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 30,7 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 8 |
| Formalladung | 0 |
| Komplexität | 122 |
| Siedepunkt | 194-196 °C (lit.) |
| Dichte | 1.035 g/mL at 25 °C (lit.) |
| Dampfdruck | 61.7Pa at 25℃ |
| Brechungsindex | n20/D 1.418(lit.) |
| Flammpunkt | 184 °F |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | Chloroform, Methanol (Slightly)Miscible with organic solvents. Slightly miscible with water. |
| Aggregatzustand | Liquid |
| Farbe | Clear amber to dark brown |
| BRN | 3588613 |
| InChI | 1S/C5H7NO2/c1-3-8-5(7)4-6-2/h3-4H2,1H3 |
| InChIKey | FPULFENIJDPZBX-UHFFFAOYSA-N |
| SMILES | CCOC(=O)C[N+]#[C-] |
| LogP (Verteilungskoeffizient) | 0.91 at 25℃ |
| CAS Datenbank | 2999-46-4(CAS DataBase Reference) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 1.8% (1 of 55) of reports.DangerH302 (89.1%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P262, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P316, P317, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 55 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Status: Active Update: 11-04-2016 https://echa.europa.eu/registration-dossier/-/registered-dossier/17093 |
| Hazard Classes and Categories | Acute Tox. 4 (89.1%) |
| F | 8-9-21 |
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | UN 2810 6.1/PG 3 |
| Zollcode | 29299090 |
| R-Sätze (R) | 20/22-20/21/22 |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 36/37/39-26-36/37-24/25 |
| Gefahrenklasse | 6.1Acute Tox. 4 InhalationAcute Tox. 4 Oral |
| Verpackungsgruppe | III |
| Lagerklasse | 10 - Combustible liquids |
Anwendungen & Verwendung
Verwenden
Ethyl Isocyanoacetate, is a cyclization synthon used to prepare pyrroles, oxazolines, benzodiazepines, oxazoles and imidazoles. Ethyl isocyanoacetate can be used to prepare pyrroles,1,2 oxazolines, benzodiazepines, oxazoles and imidazoles.
Herstellung & Synthese
synthetische
synthesis of ethyl isocyanoacetate A solution containing N-formyl glycine ethyl ester (1, 1.31 g, 10 mmol), DIPEA (2.62 g, 20 mmol) and DMAP (0.45 g, 3 mmol) in dry DCM (10 mL) was loaded in a sample loop and combined with a second stream containing triphosgene (2, 0.98 g, 3.3 mmol) also dissolved in dry DCM (10 mL) at individual channel flow rates of 0.5 mL/min. The combined stream was directed into two linked 10 mL FEP reactor vessels to achieve a 20 minutes residence time at ambient temperature. The output was collect and the solvent was carefully evaporated to 80% of its total volume. The crude material was filtered through silica (5 g) and washed with DCM (2 × 10 mL) to obtain the salt-free product. The desired product 3 was obtained as dark yellow oil after evaporation of the organic phase (1.03 g, 91 % isolated yield, >97% purity by 1H NMR).