Diethylallylmalonat
DIETHYL 2-ALLYLMALONATE · NSC 8777 · Diethyl allyl · ETHYL ALLYLMALONATE · Diethyl allylmalote · ALLYLDIETHYLMALONATE · DIETHYL ALLYLMALONATE · Diethyl allyimalonate
Identifikatoren & physikalische Daten
| CAS No. | 2049-80-1 |
|---|---|
| Summenformel | C10H16O4 |
| Durchschnittliche Molmasse | 200,23 g/mol |
| Monoisotopische Masse | 200,10485899 g/mol |
| SMILES | C=CCC(C(=O)OCC)C(=O)OCC |
| InChIKey | GDWAYKGILJJNBB-UHFFFAOYSA-N |
| PubChem CID | 74900 |
| EC No. | 218-072-9 |
| DTXSID | DTXSID30883787 |
| Lokaler Name | Diethylallylmalonat |
Chemische & physikalische Eigenschaften
| XLogP | 1,9 |
|---|---|
| Polarare Oberfläche (TPSA) | 52,6 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 8 |
| Schwere Atome | 14 |
| Formalladung | 0 |
| Komplexität | 192 |
| SpringerMaterials Properties | Diamagnetic susceptibility |
| Siedepunkt | 222-223 °C(lit.) |
| Dichte | 1.015 g/mL at 25 °C(lit.) |
| Brechungsindex | n20/D 1.431(lit.) |
| Flammpunkt | 160 °F |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Liquid |
| pKa (Säurekonstante) | 12.63±0.46(Predicted) |
| Farbe | Clear colorless to slightly yellow |
| Löslichkeit | Not miscible or difficult to mix with water. |
| BRN | 1709466 |
| InChI | 1S/C10H16O4/c1-4-7-8(9(11)13-5-2)10(12)14-6-3/h4,8H,1,5-7H2,2-3H3 |
| InChIKey | GDWAYKGILJJNBB-UHFFFAOYSA-N |
| SMILES | CCOC(=O)C(CC=C)C(=O)OCC |
| LogP (Verteilungskoeffizient) | 1.990 (est) |
| CAS Datenbank | 2049-80-1(CAS DataBase Reference) |
| NIST chemische Informationen | Propanedioic acid, 2-propenyl-, diethyl ester(2049-80-1) |
| EPA chemische Informationen | Propanedioic acid, 2-propenyl-, diethyl ester (2049-80-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 2.4% (1 of 41) of reports.WarningH315 (97.6%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Propanedioic acid, 2-propenyl-, diethyl ester |
| Weitere Sicherheitsinformationen | Evaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia |
| Hazard Classes and Categories | Skin Irrit. 2 (97.6%) |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | NA 1993 / PGIII |
| Zollcode | 29171990 |
| R-Sätze (R) | 36/37/38 |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-36-37/39 |
| Lagerklasse | 10 - Combustible liquids |
Anwendungen & Verwendung
Verwenden
Diethyl allylmalonate is an important intermediates in syntheses of vitamins B1 and B6, barbiturates, non-steroidal anti-inflammatory agents, other numerous pharmaceuticals, agrochemicals and flavors and fragrances compounds.
Herstellung & Synthese
synthetische
Diethyl allyl malonate is obtained by reacting diethyl malonate with allyl bromide. Under nitrogen atmosphere, to a 500 mL three-neck round bottom flask was added diethyl malonate (20 g), anhydrous potassium carbonate (43 g) and anhydrous CH3CN (200 mL). The reaction mixture was stirred at room temperature for 10 minutes, then allyl bromide (23 g) was slowly added to the reaction mixture at room temperature. The reaction mixture was heated to 80°C for 24 hours. The reaction mixture was cooled to room temperature and filtered through a bed of celite. The celite bed was washed with acetonitrile (100 mL) and the combined filtrates were concentrated to give diethyl allylmalonate (24 g) as a colorless liquid.