3-Oxoglutarsure
3-OXOPENTANEDIOIC ACID · ACETONEDICARBOXYLIC ACID · 3-OXOGLUTARIC ACID · ACETONE-1,3-DICARBOXYLIC ACID · BETA-KETOGLUTARIC ACID · ACETONEDIACETIC ACID · BETA-OXOGLUTARIC ACID · 4-oxo-1,7-heptanedioic acid
Identifikatoren & physikalische Daten
| CAS No. | 542-05-2 |
|---|---|
| Summenformel | C5H6O5 |
| Durchschnittliche Molmasse | 146,1 g/mol |
| Monoisotopische Masse | 146,02152329 g/mol |
| SMILES | O=C(O)CC(=O)CC(=O)O |
| InChIKey | OXTNCQMOKLOUAM-UHFFFAOYSA-N |
| PubChem CID | 68328 |
| ChEBI | CHEBI:88950 |
| EC No. | 208-797-9 |
| DTXSID | DTXSID2060252 |
| Lokaler Name | 3-Oxoglutarsure |
Chemische & physikalische Eigenschaften
| XLogP | -0,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 91,7 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 5 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 153 |
| Schmelzpunkt | 138 °C133 °C (dec.) (lit.) |
| Physical Description | Solid[Merck Index] Off-white hygroscopic powder[Acros Organics MSDS] |
| Siedepunkt | 185.67°C (rough estimate) |
| Dichte | 1.2821 (rough estimate) |
| Dampfdruck | 0.005Pa at 25℃ |
| Brechungsindex | 1.3920 (estimate) |
| Lagerbedingungen | -20°C |
| Löslichkeit | DMSO (Slightly, Heated), Methanol (Slightly)soluble |
| Aggregatzustand | Crystalline Powder |
| pKa (Säurekonstante) | pK (25°) 3.10 |
| Farbe | White |
| Merck | 14,68 |
| BRN | 1447081 |
| Stabilität | Unstable in Solution |
| InChI | 1S/C5H6O5/c6-3(1-4(7)8)2-5(9)10/h1-2H2,(H,7,8)(H,9,10)/p-2 |
| InChIKey | OXTNCQMOKLOUAM-UHFFFAOYSA-N |
| SMILES | [O-]C(=O)CC(=O)CC(=O)[O-] |
| LogP (Verteilungskoeffizient) | -0.5 at 30℃ |
| CAS Datenbank | 542-05-2(CAS DataBase Reference) |
| EPA chemische Informationen | Pentanedioic acid, 3-oxo- (542-05-2) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 13.3% (2 of 15) of reports.WarningH315 (86.7%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (86.7%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (33.3%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract 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 15 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 2 of 15 reports by companies.There are 2 notifications provided by 13 of 15 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatorische Informationen | Chemical: Pentanedioic acid, 3-oxo-Status: Cease Manufacture Update: 22-03-2013 https://echa.europa.eu/registration-dossier/-/registered-dossier/10969Status: Active Update: 19-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24040Pentanedioic acid, 3-oxo-: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | May explode if heated under confinementA skin and strong eye irritant[Acros Organics MSDS] |
| Hazard Classes and Categories | Skin Irrit. 2 (86.7%)Eye Irrit. 2 (86.7%) |
| F | 3 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29183000 |
| R-Sätze (R) | 44-36/37/38 |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 22-24/25-37/39-26-36 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Eye Irrit. 2Skin Irrit. 2 |
Anwendungen & Verwendung
Beschreibung
Aus Ethylacetat umkristallisierte Acetondicarbonsäure bildet Nadeln mit einem Schmelzpunkt von 138 ℃. Die reine Verbindung kann mehrere Monate lang über P2O5 gelagert werden. Verunreinigtes Material neigt leicht zur Decarboxylierung. Acetondicarbonsäure wird durch heißes Wasser, Säuren und Basen in Kohlenstoffdioxid und Aceton zersetzt. Die Verbindung ist sehr gut in Wasser und Alkohol und etwas in Ethylacetet und Ether löslich. Unlöslich ist es in Chloroform, Ligroin und Benzol. Eine alkoholische Acetondicarbonsäure-Lösung färbt sich bei Zusatz von Eisen(III)-chlorid weinrot. Acetondicarbonsäure findet Verwendung in der organischen Synthese, um insbesondere heterocyclische Verbindungen zu synthetisieren.
Verwenden
β-Ketoglutaric Acid is used in the synthesis of benzodiazepine derivatives. Also used in the synthesis of orally available hepatitis C virus polymerase inhibitors.