Grundinformationen
- Standard-SMILES
[C-]#[N+]CC(=O)OCC- InChIKey
FPULFENIJDPZBX-UHFFFAOYSA-N- Summenformel
- C5H7NO2
- Durchschnittliche Molmasse
- 113,11 g/mol
- Monoisotopische Masse
- 113,04767846
Namen und Bezeichner
- Bevorzugter Name
- Ethyl isocyanoacetate
- IUPAC
- ethyl 2-isocyanoacetate
- Lokaler Name
- Ethylisocyanacetat
- Englischer Name
- Ethyl isocyanoacetate
- Summenformel
- C5H7NO2
- Molmasse
- 113.11
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
2999-46-4- PubChem CID
- 533707
- DTXSID
DTXSID20184078- EC Number
- 221-077-9
- Nikkaji
- J150.099F
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,4
- Polarare Oberfläche (TPSA)
- 30,7 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 8
- Formalladung
- 0
- Komplexität
- 122
Physikochemische Eigenschaften
- Siedepunkt
- 194 · 194-196 °C (lit.)
- Dichte
- 1.035 g/mL · 1.035 g/mL at 25 °C (lit.)
- Dampfdruck
- 61.7 Pa · 61.7Pa at 25℃
- Brechungsindex
- 20 · n20/D 1.418(lit.)
- Flammpunkt
- 184 °F · 184 °F
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- Chloroform, Methanol (Slightly)
- Aggregatzustand
- Liquid
- Farbe
- Clear amber to dark brown
- Wasserlöslichkeit
- Miscible with organic solvents. Slightly miscible with water.
- BRN
- 3588613 · 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
- 0.91 at · 0.91 at 25℃
- CAS Datenbank
- 2999 · 2999-46-4(CAS DataBase Reference)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 1.8% (1 of 55) of reports.
Danger
H302 (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.
Gefahrenhinweise
Sicherheitsdaten
- F
- 8-9-21
- wgk
- 3
- ridadr
- UN 2810 6.1/PG 3
- hs_code
- 29299090
- risk_code
- 20/22-20/21/22
- hazard_code
- Xn
- safety_code
- 36/37/39-26-36/37-24/25
- hazard_class
- 6.1
- packing_group
- III
- Speicherklasse
- 10 - Combustible liquids
- Hazard Classifications
- Acute Tox. 4 InhalationAcute Tox. 4 Oral
Chemie und Industrie
Anwendungen
VerwendenEthyl 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.
Darstellung
synthetischesynthesis 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).
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