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Diethylethoxymethylenmalonat
EMME · Diethyl 2-(ethoxymethylene)malonate · DEEMM · Diethyl 2-(ethoxymethylene)propanedioate · diethyl (ethoxymethylidene)propanedioate · ETHOXYMETHYLENEMALONIC ACID DIETHYL ESTER · 2-Ethoxymethylene-malonic acid diethyl ester · onate
Identifikatoren & physikalische Daten
| CAS No. | 87-13-8 |
|---|---|
| Summenformel | C10H16O5 |
| Durchschnittliche Molmasse | 216,23 g/mol |
| Monoisotopische Masse | 216,09977361 g/mol |
| SMILES | CCOC=C(C(=O)OCC)C(=O)OCC |
| InChIKey | LTMHNWPUDSTBKD-UHFFFAOYSA-N |
| PubChem CID | 6871 |
| EC No. | 201-725-7 |
| DTXSID | DTXSID5052591 |
| Lokaler Name | Diethylethoxymethylenmalonat |
Chemische & physikalische Eigenschaften
| XLogP | 1,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 61,8 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 5 |
| Frei drehbare Bindungen | 8 |
| Schwere Atome | 15 |
| Formalladung | 0 |
| Komplexität | 224 |
| Stoffklassen | Other Classes -> Esters, OtherIndustrial compound |
| Physical Description | Colorless liquid[Alfa Aesar MSDS] |
| Ionization Efficiency | Positive2.12.7Agilent XCTElectrospray ionizationformic acid (5.3nM) |
| Collision Cross Section | 146.8 Ų [M+Na]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: TOXCASTSource Identifier: DTXSID5052591] |
| Schmelzpunkt | -33°C |
| Siedepunkt | 279-283 °C(lit.) |
| Dichte | 1.080 g/mL at 20 °C(lit.) |
| Dampfdruck | <0.1 hPa |
| Brechungsindex | n20/D 1.463 |
| Flammpunkt | 311 °F |
| Lagerbedingungen | Store below +30°C. |
| Löslichkeit | Chloroform (Slightly), Ethyl Acetate (Slightly)insoluble |
| Aggregatzustand | Liquid |
| Farbe | Clear colorless to light yellow |
| BRN | 880058 |
| InChI | 1S/C10H16O5/c1-4-13-7-8(9(11)14-5-2)10(12)15-6-3/h7H,4-6H2,1-3H3 |
| InChIKey | LTMHNWPUDSTBKD-UHFFFAOYSA-N |
| SMILES | CCO\C=C(\C(=O)OCC)C(=O)OCC |
| LogP (Verteilungskoeffizient) | 1.5-2.1 at pH7 |
| CAS Datenbank | 87-13-8(CAS DataBase Reference) |
| NIST chemische Informationen | Propanedioic acid, (ethoxymethylene)-, diethyl ester(87-13-8) |
| EPA chemische Informationen | Propanedioic acid, (ethoxymethylene)-, diethyl ester (87-13-8) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH302 (99.1%): Harmful if swallowed [Warning Acute toxicity, oral]P260, P261, P264, P264+P265, P270, P271, P272, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 111 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Status: Active Update: 29-03-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/12518Diethyl ethoxymethylenemalonate: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | A moderate skin irritantCauses somnolence and gastrointestinal changes in oral lethal-dose studies of rats[RTECS] An irritantMay cause skin and respiratory sensitizationHarmful by ingestion[Alfa Aesar MSDS] Search for (87-13-8[EC/RN Number]) AND (allergic OR dermatitis OR asthma OR sensitizer OR sensitization): no results[PubMed] |
| Peroxide Forming Chemical | Diethyl ethoxymethylenemalonateD: Other compounds that may form peroxidesKelly |
| Hazard Classes and Categories | Acute Tox. 4 (99.1%) |
| Toxicity Data | LCLo (mouse) = 44 mg/m3 |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29189090 |
| RTECS-Nr. | OO1100000 |
| R-Sätze (R) | 22-36/37/38-42/43 |
| Toxizität | LD50 orally in Rabbit: 925 mg/kg LD50 dermal Rat > 2000 mg/kg |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 26-36/37/39-27-24/25 |
| Lagerklasse | 10 - Combustible liquids |
| Gefahrenklasse | Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 2Eye Irrit. 2Skin Irrit. 2Skin Sens. 1A |
| Selbstentzündungstemperatur | 215 °C |
Anwendungen & Verwendung
Verwenden
Diethyl ethoxymethylenemalonate is used for synthesis of pyrido[3,2-e]pyrimido[1,2-c]pyrimidines. Initially, it was used to monitor lysine decarboxylase activity. It is useful in the determination of amino acids by precolumn derivatization by using reversed-phase high-performance liquid chromatography (HPLC). It plays an important role in the Gould-Jacobs reaction to prepare quinolines. For example, anile reacts with this reagent to give 4-hydroxyquinoline. It acts as an intermediate in the production of flumequine, which is a fluoroquinolone antibiotic.