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Dimethylmalonat
DMM · METHYL MALONATE · MALONIC ACID DIMETHYL ESTER · Dimethyl propanedioate · dimthyl malonate · DIMETHYL MALONAT · dimethyl1,3-propanedioate · MINA-009
Identifikatoren & physikalische Daten
| CAS No. | 108-59-8 |
|---|---|
| Summenformel | C5H8O4 |
| Durchschnittliche Molmasse | 132,11 g/mol |
| Monoisotopische Masse | 132,04225874 g/mol |
| SMILES | COC(=O)CC(=O)OC |
| InChIKey | BEPAFCGSDWSTEL-UHFFFAOYSA-N |
| PubChem CID | 7943 |
| ChEMBL | CHEMBL1986332 |
| EC No. | 203-597-8 |
| DTXSID | DTXSID4029145 |
| Lokaler Name | Dimethylmalonat |
Chemische & physikalische Eigenschaften
| XLogP | 0 |
|---|---|
| Polarare Oberfläche (TPSA) | 52,6 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 9 |
| Formalladung | 0 |
| Komplexität | 104 |
| Stoffklassen | Other Classes -> Esters, Other |
| SpringerMaterials Properties | Boiling point |
| LogP (Verteilungskoeffizient) | -0.05 |
| Aromastoffe | EU Flavoring substances |
| Dampfdruck | 14.7 [mmHg]0.15 hPa (20 °C) |
| Physical Description | Liquid[Merck Index] Colorless liquid with an ester-like odor[OECD SIDS: Malonic Acid Diesters - 2005] |
| Ionization Efficiency | Positive1.582.7Agilent XCTElectrospray ionizationformic acid (5.3nM) |
| Schmelzpunkt | -62 °C (lit.) |
| Siedepunkt | 180-181 °C (lit.) |
| Dichte | 1.156 g/mL at 25 °C (lit.) |
| Dampfdichte | >1 (vs air) |
| Brechungsindex | n20/D 1.413(lit.) |
| Flammpunkt | 194 °F |
| Lagerbedingungen | Store below +30°C. |
| Löslichkeit | alcohol: misciblenegligible |
| pKa (Säurekonstante) | 11.80±0.46(Predicted) |
| Aggregatzustand | Liquid |
| Farbe | Clear colorless |
| Geruch | fruity |
| Explosionsgrenze | 1.3-17.4%(V) |
| Merck | 14,6096 |
| BRN | 774261 |
| Henry-Konstante | 3.8×101 mol/(m3Pa) at 25℃, Katrib et al. (2003) |
| Dielektrizitätskonstante | 10.4(20℃) |
| Stabilität | Stable. Incompatible with strong oxidizing agents. Flammable. |
| InChI | 1S/C5H8O4/c1-8-4(6)3-5(7)9-2/h3H2,1-2H3 |
| InChIKey | BEPAFCGSDWSTEL-UHFFFAOYSA-N |
| SMILES | COC(=O)CC(=O)OC |
| LogP (Verteilungskoeffizient) | -0.05 at 20-25℃ and pH6.4 |
| CAS Datenbank | 108-59-8(CAS DataBase Reference) |
| NIST chemische Informationen | Propanedioic acid, dimethyl ester(108-59-8) |
| EPA chemische Informationen | Dimethyl malonate (108-59-8) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 86.3% (1530 of 1773) of all reports.WarningH319 (13.6%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)Aggregated GHS information provided per 1773 reports by companies from 16 notifications to the ECHA C&L Inventory. |
|---|---|
| Regulatorische Informationen | Chemical: Propanedioic acid, dimethyl esterCommission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Propanedioic acid, 1,3-dimethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Propanedioic acid, 1,3-dimethyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 04-05-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/20020Dimethyl malonate: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to human health |
| Gefahrenübersicht | Causes no skin irritation and mild to moderate eye irritation in rabbitsNo adverse effects observed in oral or dermal lethal-dose studies of rats (LD50s > 2,000 mg/kg)Reversible hepatocellular hypertrophy (considered indicative of liver metabolism rather than systemic toxicity) observed in an oral repeated-dose study of rats at the highest tested dose (1,000 mg/kg/day)No evidence of reproductive toxicity, developmental toxicity, or mutagenicity[OECD SIDS: Malonic Acid Diesters - 2005] May cause irritation[Alfa Aesar MSDS] |
| Hazard Classes and Categories | Eye Irrit. 2 (13.6%) |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | NA1993 |
| Zollcode | 29171910 |
| RTECS-Nr. | OO0950000 |
| R-Sätze (R) | 36/37/38 |
| Toxizität | LD50 orally in Rabbit: 5331 mg/kg LD50 dermal Rabbit > 5000 mg/kg |
| Gefahrensymbole | Xi |
| hazard_note | Irritant |
| Sicherheitshinweise (S) | 26-36 |
| Gefahrenklasse | CBLEye Irrit. 2 |
| Lagerklasse | 10 - Combustible liquids |
| Selbstentzündungstemperatur | 440 °C |
Anwendungen & Verwendung
Beschreibung
Dimethyl malonate is a diester derivative of malonic acid. It is a common reagent for organic synthesis used, for example, as a precursor for barbituric acid. It is also used in the malonic ester synthesis. It can be synthesized from dimethoxymethane and carbon monoxide.
Verwenden
Dimethyl malonate is a reagent used in organic synthesis. It acts as a precursor for the synthesis of mono-substituted and di-substituted acetic acid, barbiturates, vitamin B1 and vitamin B6. It is used in the pharmaceutical industry to prepare pharmaceuticals like chloroquine and butazolidin. It is involved in the synthesis of diastereomeric pure thienylpyridines by reacting with 1,3-diphenylprop-2-enyl acetate.