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5,5-DIMETHYL-1-PYRROLINE N-OXIDE

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5,5-DIMETHYL-1-PYRROLINE N-OXIDE Basic information
5,5-DIMETHYL-1-PYRROLINE N-OXIDE Chemical Properties
  • Melting point:25-29 °C(lit.)
  • Boiling point:75 °C0.4 mm Hg(lit.)
  • Density 1.015 g/mL at 25 °C(lit.)
  • refractive index n20/D 1.496(lit.)
  • Flash point:204 °F
  • storage temp. −20°C
  • pka2.47±0.40(Predicted)
  • form Pale yellow solid or oil.
  • Merck 14,3393
  • BRN 107603
  • Stability: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.
  • InChIKeyVCUVETGKTILCLC-UHFFFAOYSA-N
  • CAS DataBase Reference3317-61-1(CAS DataBase Reference)
Safety Information
  • Safety Statements 24/25
  • WGK Germany 3
  • 8-10
  • HazardClass IRRITANT
  • HS Code 29339900
MSDS
5,5-DIMETHYL-1-PYRROLINE N-OXIDE Usage And Synthesis
  • Chemical Propertieswhite to faintly yellow solid
  • UsesSpin trap agent for biological systems.
  • PreparationTo 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).
    Preparation of 5,5-dimethyl-l-pyrroline-N-oxide
  • Biological ActivityWater soluble nitric oxide spin trap; allows the measurement of oxygen-centered free radicals in biological systems at room temperature using electron spin resonance (ESR). Has a high reaction rate constant for superoxide and hydroxyl radicals, and distinguishes simultaneously among a variety of important biologically generated free radicals.
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