5336-95-8

Basic information

• Product Name: 1-nitropyrrolidine-2,5-dione
• Synonyms: 1-Nitro-2,5-pyrrolidine-dione; Succinimide, N-nitro-
• CAS NO: 5336-95-8
• Molecular Formula: C₄H₄N₂O₄
• Molecular Weight: 144.0856
• Mol File: 5336-95-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 290.4°C at 760 mmHg
• Flash Point: 129.4°C
• Density: 1.6g/cm³
• Vapor Pressure: 0.00208mmHg at 25°C
• Refractive Index: 1.552
• CAS DataBase Reference: 1-nitropyrrolidine-2,5-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-nitropyrrolidine-2,5-dione(5336-95-8)
• EPA Substance Registry System: 1-nitropyrrolidine-2,5-dione(5336-95-8)

Safety Data

• Hazardous Substances Data: 5336-95-8(Hazardous Substances Data)

Usage

Physical state

Yellow crystalline solid

Common uses

Organic synthesis, precursor for pharmaceuticals and agrochemicals

Versatility

Building block in organic chemistry, starting material for nitrogen-containing compound synthesis

Functionality

Nitro functionality, useful reagent for carbon-carbon bond and heterocycle formation

Value

Potential for various reactions and complex structure formation, valuable in pharmaceutical and agrochemical R&D.

Upstream product

• 123-56-8 Succinimide 

Downstream Products

• 134450-66-1 9-phenyl-10-nitroanthracene 
• 84-65-1 9,10-phenanthrenequinone 
• 676-47-1 potassium succinate 
• 110-15-6 succinic acid 

Relevant articles and documents

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Synthetic Diversity from a Versatile and Radical Nitrating Reagent

We leverage the slow liberation of nitrogen dioxide from a newly discovered, inexpensive succinimide-derived reagent to allow for the C?H diversification of alkenes and alkynes. Beyond furnishing a library of aryl β-nitroalkenes, this reagent provides unparalleled access to β-nitrohydrins and β-nitroethers. Detailed mechanistic studies strongly suggest that a mesolytic N?N bond fragmentation liberates a nitryl radical. Using in situ photo-sensitized, electron paramagnetic resonance spectroscopy, we observed direct evidence of a nitryl radical in solution by nitrone spin-trapping. To further exhibit versatility of N-nitrosuccinimide under photoredox conditions, the late-stage diversification of an extensive number of C?H partners to prepare isoxazolines and isoxazoles is presented. This approach allows for the formation of an in situ nitrile oxide from a ketone partner, the presence of which is detected by the formation of the corresponding furoxan when conducted in the absence of a dipolarophile. This 1,3-dipolar cycloaddition with nitrile oxides and alkenes or alkynes proceeds in a single-operational step using a mild, regioselective, and general protocol with broad chemoselectivity.

Succinimidylation and nitration of aromatic compounds by photolysis with N-nitrosuccinimide

N-Nitrosuccinimide (S-NO2) engages in weak charge transfer complexes with aromatic compounds (ArH).Upon photolysis with light of λ > 345 nm in dichloromethane, electron transfer within the charge transfer complex leads to the triad -NO2>from which products of eventual succinimidylation and/or nitration develop by initial attack of succinimide anion upon the radical cation.Photolysis in the presence of trifluoroacetic acid (0.4 mol dm-3) causes inactivation of S- by protonation, making EPR detection of ArH-radical cations or radicals cations formed by its further transformations possible.In acetonitrile, trifluoroacetic acid is too weak effectively to protonate S-, whereas addition of stronger acids again leads to the development of EPR spectra of ArH-radical cation in the case of 9,10-dimethylanthracene, the intensity increasing with decreasing pK of the acid.An X-ray crystal structure is reported for N-nitrosuccinimide.