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| | Ethyl isocyanoacetate Basic information |
| | Ethyl isocyanoacetate Chemical Properties |
| Boiling point | 194-196 °C (lit.) | | density | 1.035 g/mL at 25 °C (lit.) | | vapor pressure | 61.7Pa at 25℃ | | refractive index | n20/D 1.418(lit.) | | Fp | 184 °F | | storage temp. | 2-8°C | | solubility | Chloroform, Methanol (Slightly) | | form | Liquid | | color | Clear amber to dark brown | | Water Solubility | Miscible with organic solvents. Slightly miscible with water. | | Sensitive | Moisture & Light Sensitive | | BRN | 3588613 | | Exposure limits | NIOSH: IDLH 25 mg/m3 | | 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 25℃ | | CAS DataBase Reference | 2999-46-4(CAS DataBase Reference) |
| Hazard Codes | Xn | | Risk Statements | 20/22-20/21/22 | | Safety Statements | 36/37/39-26-36/37-24/25 | | RIDADR | UN 2810 6.1/PG 3 | | WGK Germany | 3 | | F | 8-9-21 | | HazardClass | 6.1 | | PackingGroup | III | | HS Code | 29299090 | | Storage Class | 10 - Combustible liquids | | Hazard Classifications | Acute Tox. 4 Inhalation
Acute Tox. 4 Oral |
| | Ethyl isocyanoacetate Usage And Synthesis |
| Chemical Properties | Light yellow to brom liquid. Slightly soluble in water and lye, miscible in ethanol and ether. | | Uses | 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. | | Uses | Ethyl isocyanoacetate is used in the syntheses of 7-aza-tetrahydroindoles, oxazolines, benzodiazepines, imidazoles and oxazoles. For example, it is involved in the synthesis of 1H-indole-2-carboxylate by condensing with 2-bromo benzenealdehyde using CuI as a catalyst. It is a precursor used in the preparation of ethyl thiazole-4-carboxylate upon reaction with O-ethyl thioformate. | | Preparation | 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). | | General Description | Material may darken upon storage |
| | Ethyl isocyanoacetate Preparation Products And Raw materials |
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