Glutarimid
PIPERIDINE-2,6-DIONE · NSC 58190 · NSC 168666 · GLUTARIMIDE · Glutarimide98% · Glutarimide>2,6-Dioxopiperidine · 2,6-PIPERIDINEDIONE · 2,6-DIKETOPIPERIDINE
Identifikatoren & physikalische Daten
| CAS No. | 1121-89-7 |
|---|---|
| Summenformel | C5H7NO2 |
| Durchschnittliche Molmasse | 113,11 g/mol |
| Monoisotopische Masse | 113,04767846 g/mol |
| SMILES | O=C1CCCC(=O)N1 |
| InChIKey | KNCYXPMJDCCGSJ-UHFFFAOYSA-N |
| PubChem CID | 70726 |
| ChEMBL | CHEMBL3763941 |
| ChEBI | CHEBI:5435 |
| EC No. | 214-340-4 |
| DTXSID | DTXSID7074452 |
| Lokaler Name | Glutarimid |
Chemische & physikalische Eigenschaften
| XLogP | -0,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 46,2 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 8 |
| Formalladung | 0 |
| Komplexität | 116 |
| SpringerMaterials Properties | Boiling point |
| Schmelzpunkt | 155-157 °C (lit.) |
| Siedepunkt | 211.82°C (rough estimate) |
| Dichte | 1.2416 (rough estimate) |
| Brechungsindex | 1.4200 (estimate) |
| Lagerbedingungen | Inert atmosphere,Room Temperature |
| Löslichkeit | soluble in Chloroform, DCMSoluble in water, hot ethanol and boiling benzene. Insoluble in ether. |
| Aggregatzustand | Crystals or Crystalline Flakes |
| pKa (Säurekonstante) | pKa 11.4 (Uncertain) |
| Farbe | White |
| BRN | 110052 |
| InChI | InChI=1S/C5H7NO2/c7-4-2-1-3-5(8)6-4/h1-3H2,(H,6,7,8) |
| InChIKey | KNCYXPMJDCCGSJ-UHFFFAOYSA-N |
| SMILES | N1C(=O)CCCC1=O |
| CAS Datenbank | 1121-89-7(CAS DataBase Reference) |
| EPA chemische Informationen | Glutarimide (1121-89-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH315 (100%): 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)The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory. |
|---|---|
| Regulatorische Informationen | Chemical: 2,6-Piperidinedione |
| Hazard Classes and Categories | Skin Irrit. 2 (100%) |
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 29251995 |
| RTECS-Nr. | MA4000000 |
| R-Sätze (R) | 36 |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 37/39-26 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Verwenden
Glutarimide acts as an inhibitor of protein synthesis. Further, it is used as a reactant for thionations and biocatalytic asymmetric synthesis of sitagliptin production. It is also employed in the generation of beta-adrenoceptor ligands, enantioselective synthesis of securinega alkaloids and alfa-fluoro-alfa amino amides. In addition to this, it is used in intramolecular amidocyclopropanation reactions.
Herstellung & Synthese
synthetische
To a flask containing 70 gm (0.53 mole) of glutaric acid is added 150 ml (2.2 mole) of 28% aqueous ammonia. The mixture is set for distillation and heated for 7 hr as the temperature of the mixture rises from 90° to 180°C. The temperature is held at 170-180°C for \\ hr or until the evolution of ammonia ceases. The reaction mixture solidifies on cooling and the product is recrystallized from acetone to afford 37.4 gm (63%), m.p. 145-146°C. t may be advantageous to preform the ammonium salt of dicarboxylic acids prior to the application of enough heat to form the imide. The preparation of succinimide is a case in point.