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

5,5-DIMETHYL-1-PYRROLINE N-OXIDE Structure
CAS No.
3317-61-1
Chemical Name:
5,5-DIMETHYL-1-PYRROLINE N-OXIDE
Synonyms
DMPO;2,2-DIMETHYL-3,4-DIHYDRO-2H-PYRROLE 1-OXIDE;5,5-dimethyl-1-pyrroline-1-oxide;3,4-DIHYDRO-2,2-DIMETHYL-2H-PYRROLE 1-OXIDE;Dimethyl N;spintrappingreagent;,5-Dimethyl-1-pyrroline N-oxide;5,5-DIMETHYL-1-PYRROLINE N-OXIDE;5,5-Dimethyl-1-Pyrrolidine-N-oxide;5,5-Dimethyl-1-pyrrolineN-Oxide>
CBNumber:
CB3290637
Molecular Formula:
C6H11NO
Molecular Weight:
113.16
MOL File:
3317-61-1.mol
MSDS File:
SDS
Modify Date:
2023/6/8 17:06:37

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

Melting point 25-29 °C (lit.)
Boiling point 75 °C/0.4 mmHg (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
solubility Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml).
form Pale yellow solid or oil.
pka 2.47±0.40(Predicted)
color Pale yellow
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.
InChIKey VCUVETGKTILCLC-UHFFFAOYSA-N
CAS DataBase Reference 3317-61-1(CAS DataBase Reference)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P280-P305+P351+P338-P321
Safety Statements  24/25
WGK Germany  3
8-10
HazardClass  IRRITANT
HS Code  29339900
NFPA 704
1
0 0

5,5-DIMETHYL-1-PYRROLINE N-OXIDE price More Price(3)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) 92688 5,5-Dimethyl-1-pyrroline N-oxide for ESR-spectroscopy 3317-61-1 100MG ₹12156.48 2022-06-14 Buy
TCI Chemicals (India) D2362 5,5-Dimethyl-1-pyrroline N-Oxide min. 97.0 % 3317-61-1 1G ₹17000 2022-05-26 Buy
TCI Chemicals (India) D2362 5,5-Dimethyl-1-pyrroline N-Oxide min. 97.0 % 3317-61-1 5G ₹30800 2022-05-26 Buy
Product number Packaging Price Buy
92688 100MG ₹12156.48 Buy
D2362 1G ₹17000 Buy
D2362 5G ₹30800 Buy

5,5-DIMETHYL-1-PYRROLINE N-OXIDE Chemical Properties,Uses,Production

Description

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.

Chemical Properties

white to faintly yellow solid

Uses

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.

Preparation

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).
Preparation of 5,5-dimethyl-l-pyrroline-N-oxide

Biological Activity

Water 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.

Physiological effects

5,5-dimethyl-1-pyrroline N-oxide is used as a spin trap for the study of radicals formed by enzymatic acetaldehyde oxidation. It has a role as a neuroprotective agent and a spin trapping reagent.

5,5-DIMETHYL-1-PYRROLINE N-OXIDE Preparation Products And Raw materials

Raw materials

Preparation Products

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5,5-DIMETHYL-1-PYRROLINE N-OXIDE 5,5-Dimethyl-1-pyrroline N-oxide [spin trapping spintrappingreagent 1-Oxylato-2,2-dimethyl-3,4-dihydro-2H-pyrrole-1-ium 3,4-Dihydro-1-oxylato-2,2-dimethyl-2H-pyrrolium 5,5-Dimethyl-1-Pyrrolidine-N-oxide 5,5-DIMETHYL-1-PYRROLINE N-OXIDE, [SPIN TRAPPING REAGENT] 5,5-DIMETHYL-1-PYRROLINE N-OXIDE [SPIN TRAPPING REAGENT] 97+% 5,5-DIMETHYL-1-PYRROLINE N-OXIDE 99% 2,2-dimethyl-1-oxidanidyl-3,4-dihydropyrrol-1-ium 2,2-dimethyl-1-oxido-1-pyrrolin-1-ium 2,2-dimethyl-1-oxido-3,4-dihydropyrrol-1-ium 5,5-Dimethyl-1-pyrroline N-oxide ,97% 5,5-Dimethyl-1-pyrroline N-oxide,DMPO 2,2-diMethyl-2,3-dihydro-1H-pyrrole 1-oxide ,5-Dimethyl-1-pyrroline N-oxide Dimethyl N 5,5-Dimethyl-1-pyrrolineN-Oxide> 2,2-Dimethyl-3,4-Dihydro-2H-Pyrrole 1-Ox 3,4-Dihydro-2,2-dimethyl-2H-pyrrole N-oxide 95% DMPO 2,2-DIMETHYL-3,4-DIHYDRO-2H-PYRROLE 1-OXIDE 5,5-dimethyl-1-pyrroline-1-oxide 3,4-DIHYDRO-2,2-DIMETHYL-2H-PYRROLE 1-OXIDE 5,5-Dimethyl-1-pyrroline N-Oxide, ≥ 97.0% 3317-61-1 Enzymes, Inhibitors, and Substrates Pyrrolines Nitric Oxide Metabolism Nitric Oxide Scavengers ESR Spectrometry Spin Trapping Reagents Building Blocks Biochemicals and Reagents Application Index BioChemical Cell Signaling Enzymes Heterocyclic Building Blocks pharmacetical Analytical Chemistry ESR Spectrometry Spin Trapping Reagents