5,5-Dimethyl-1-pyrroline N-oxide

Base Information

• Chemical Name: 5,5-Dimethyl-1-pyrroline N-oxide
• CAS No.: 3317-61-1
• Molecular Formula: C6H11NO
• Molecular Weight: 113.159
• Hs Code.: 29339900
• European Community (EC) Number: 222-011-1
• UNII: 7170JZ1QF3
• DSSTox Substance ID: DTXSID30186826
• Nikkaji Number: J205.397G
• Wikidata: Q27265933
• ChEMBL ID: CHEMBL79824
• Mol file: 3317-61-1.mol

Synonyms:5,5-dimethyl-1-pyrroline-1-oxide;5,5-dimethyl-1-pyrroline-N-oxide;5,5-DMPO;DMPO-5,5

Chemical Property of 5,5-Dimethyl-1-pyrroline N-oxide

Chemical Property:

• Appearance/Colour: white to faintly yellow solid
• Vapor Pressure: 0.00918mmHg at 25°C
• Melting Point: 25-29 °C(lit.)
• Refractive Index: n20/D 1.496(lit.)
• Boiling Point: 274.2 °C at 760 mmHg
• PKA: 2.47±0.40(Predicted)
• Flash Point: 130.7 °C
• PSA: 28.75000
• Density: 0.96 g/cm³
• LogP: 1.09870
• Storage Temp.: −20°C
• Solubility.: Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml).
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 113.084063974
• Heavy Atom Count: 8
• Complexity: 127

Purity/Quality:

98% ^*data from raw suppliers

DMPO ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Biochemical Research
• Canonical SMILES: CC1(CCC=[N+]1[O-])C
• 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.
• Uses: Spin trap agent for biological systems. 5,5-Dimethyl-1-pyrroline N-oxide has been used as a spin trapping reagent to detect free radicals in electron paramagnetic resonance (EPR) based reactions. 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.

Technology Process of 5,5-Dimethyl-1-pyrroline N-oxide

There total 9 articles about 5,5-Dimethyl-1-pyrroline N-oxide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 60.0%

4-methyl-4-nitropentanal (57620-49-2) → 5,5-Dimethyl-1-pyrroline N-oxide (3317-61-1)

Guidance literature:

With acetic acid; zinc; In ethanol; at 1 ℃; for 48h;

DOI:10.1021/jo00372a039

Reference yield: 31.0%

2-<3-methyl-3-nitrobutyl>-1:3-dioxolan → 2,2-dimethyl-3,4-dihydro-2H-pyrrole (2045-76-3) + 5,5-Dimethyl-1-pyrroline N-oxide (3317-61-1)

Guidance literature:

With hydrogen; palladium on activated charcoal;

Reference yield:

2-(3-methyl-3-nitrobutyl)-[1,3]dioxolane (57620-56-1) → 5,5-Dimethyl-1-pyrroline N-oxide (3317-61-1)

Guidance literature:

With hydrogenchloride; ammonium chloride; zinc;

upstream raw materials:

5,5-dimethyl-1-pyrroline-2-carboxylic acid 1-oxide

4-methyl-4-nitropentanal

2-(3-methyl-3-nitrobutyl)-[1,3]dioxolane

2,2-dimethyl-5-hydroperoxy-1-pyrrolidinyloxyl

Downstream raw materials:

(3aR,8aS,8bS)-6,6-Dimethyl-2-phenyl-hexahydro-dipyrrolo[1,2-b;3',4'-d]isoxazole-1,3-dione

(3aR,8aR,8bS)-6,6-Dimethyl-2-phenyl-hexahydro-dipyrrolo[1,2-b;3',4'-d]isoxazole-1,3-dione

Hexahydro-2'(2-phenylethyl)-2',6',6'-trimethyl-spiroisoxazole>

(2R,3R,3aR)-3-Diphenylphosphanyl-2,6,6-trimethyl-hexahydro-pyrrolo[1,2-b]isoxazole

Refernces

• 1、 Khoroshunova, Yulia V.,Morozov, Denis A.,Taratayko, Andrey I.,Gladkikh, Polina D.,Glazachev, Yuri I.,Kirilyuk, Igor A.. "Synthesis of 1-azaspiro[4.4]nonan-1-oxyls via intramolecular 1,3-dipolar cycloaddition". . p. 2036 - 2042. Retrieved 2019/09/30.
• 2、 Baskaran, S.,Trivedi, Girish.K.. "Cycloaddition Reaction of 2,2-Dimethyl-3,4-dihydro-2H-pyrrole N-Oxide With Unsaturated Sugar Lactones and Esters". . p. 1853 - 1864. Retrieved 2007/10/03.