3,4-Dihydro-2,2-dimethyl-2H-pyrrol-1-oxid
DMPO · 2,2-DIMETHYL-3,4-DIHYDRO-2H-PYRROLE 1-OXIDE · 3,4-DIHYDRO-2,2-DIMETHYL-2H-PYRROLE 1-OXIDE · 5,5-dimethyl-1-pyrroline-1-oxide · Dimethyl N · spintrappingreagent · DMPO, hydrophilic spin trap · ,5-Dimethyl-1-pyrroline N-oxide
Identifikatoren & physikalische Daten
| CAS No. | 3317-61-1 |
|---|---|
| Summenformel | C6H11NO |
| Durchschnittliche Molmasse | 113,16 g/mol |
| Monoisotopische Masse | 113,08406397 g/mol |
| SMILES | CC1(C)CCC=[N+]1[O-] |
| InChIKey | VCUVETGKTILCLC-UHFFFAOYSA-N |
| PubChem CID | 1774 |
| ChEMBL | CHEMBL79824 |
| ChEBI | CHEBI:149489 |
| EC No. | 222-011-1 |
| DTXSID | DTXSID30186826 |
| Lokaler Name | 3,4-Dihydro-2,2-dimethyl-2H-pyrrol-1-oxid |
Chemische & physikalische Eigenschaften
| XLogP | -0,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 28,8 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 8 |
| Formalladung | 0 |
| Komplexität | 126 |
| Stoffklassen | Other Uses -> Biochemical Research |
| Physical Description | White solidHighly hygroscopic[Merck Index] Light yellow, hygroscopic solidified mass or fragmentsmp = 25-29 deg C[Sigma-Aldrich MSDS] |
| Schmelzpunkt | 25-29 °C (lit.) |
| Siedepunkt | 75 °C/0.4 mmHg (lit.) |
| Dichte | 1.015 g/mL at 25 °C (lit.) |
| Brechungsindex | n20/D 1.496(lit.) |
| Flammpunkt | 204 °F |
| Lagerbedingungen | -20°C |
| Löslichkeit | Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml). |
| Aggregatzustand | Pale yellow solid or oil. |
| pKa (Säurekonstante) | 2.47±0.40(Predicted) |
| Farbe | Pale yellow |
| Merck | 14,3393 |
| BRN | 107603 |
| Stabilität | Stable, but light sensitive, hygroscopic and heat sensitive. Store in the dark, under an inert gas, and keep cold. Incompatible with strong oxidizing agents, moisture. |
| InChI | 1S/C6H11NO/c1-6(2)4-3-5-7(6)8/h5H,3-4H2,1-2H3 |
| InChIKey | VCUVETGKTILCLC-UHFFFAOYSA-N |
| SMILES | CC1(C)CCC=[N+]1[O-] |
| CAS Datenbank | 3317-61-1(CAS DataBase Reference) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 100% (2 of 2) of all reports.Not ClassifiedAggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory. |
|---|---|
| Gefahrenübersicht | May cause irritation[Sigma-Aldrich MSDS] |
| Hazard Classes and Categories | Not Classified |
| F | 8-10 |
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 29339900 |
| Sicherheitshinweise (S) | 24/25 |
| Gefahrenklasse | IRRITANT |
| Lagerklasse | 10 - Combustible liquids |
Anwendungen & Verwendung
Beschreibung
Free radicals are highly reactive, short-lived species. Spin traps react with radicals, forming stable adducts that can be further studied. DMPO is a commonly-used spin trap that reacts with O-, N-, S-, and C-centered radicals. This allows their characterization when used in association with electron spin resonance and immuno-spin trapping. DMPO is water-soluble, rapidly penetrates lipid bilayers, has low toxicity, and can be used in vitro and in vivo.
Verwenden
5,5-Dimethyl-1-pyrroline N-oxide is a reagent generally used either as a free-radical spin-trapping agent, or electrophilic component during the synthesis of pyrrolidine derivatives. It may also be considered as 1,3-dipole in cycloaddition processes.
Herstellung & Synthese
synthetische
To a three-necked round bottom flask equipped with a condenser, addition funnel, thermometer, and mechanical stirrer and containing 300 ml. 95% ethanol precooled to 2°C is added, all at once, 14.5 g (0.1 mole) 4-methyl-4-nitropentanol, and 13.1 g (1.2 mole) zinc dust. With rapid agitation, the glacial acetic acid (24.0 g, 0.4 mole) is added dropwise over a 1-hr period while maintaining the reaction temperature below 15°C. The mixture is stirred vigorously for 2 hr and then stored in the refrigerator for 2 days, at approximately 1°C. Then the zinc acetate is filtered and rinsed with 100 ml of ethanol. The combined ethanol factions are rotoevapo-rated to give the crude nitrone. The crude nitrone is dissolved in a 200 ml portion of dichloromethane and the latter washed two times with saturated sodium bicarbonate solution. The organic layer is dried over sodium sulfate and the solvent rotoevaporated, to give 10.7 (94% yield) of the crude nitrone. The product was purified by double distillation (b.p. 53°C, 0.1 Torr), to give 6.8 g (60%) of the pure nitrone as a white hygroscopic solid. The H1 NMR (400 MH CDC13, Me4Si) is 6.80 (t, 2H, methylene bound to quaternary C, J = 7.2Hg), 1.43 (s, 6H, methyl), C13NMr (100 MH2, CDC13, Me4 Si) 5=132.4 (Vinyl), 73.5 (quaternary), 34.1 (Allyl), 25.3 (methylene bound to quaternary C), 24.4 (methyls).