5336-95-8

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

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

Relevant academic research and scientific papers

N-Nitroheterocycles: Bench-Stable Organic Reagents for Catalytic Ipso-Nitration of Aryl- And Heteroarylboronic Acids

Photocatalytic and metal-free protocols to access various aromatic and heteroaromatic nitro compounds through ipso-nitration of readily available boronic acid derivatives were developed using non-metal-based, bench-stable, and recyclable nitrating reagents. These methods are operationally simple, mild, regioselective, and possess excellent functional group compatibility, delivering desired products in up to 99% yield.

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.

A novel transition metal free [bis-(trifluoroacetoxy)iodo]benzene (PIFA) mediated oxidative ipso nitration of organoboronic acids

A mild, convenient and transition metal free methodology for oxidative ipso nitration of diversely functionalized organoboronic acids, including heteroaryl- and alkylboronic acids, has been developed at ambient temperature using a combination of [bis-(trifluoroacetoxy)]iodobenzene (PIFA) - N-bromosuccinimide (NBS) and sodium nitrite as the nitro source. It is anticipated that the reaction proceeds through in situ generation of NO2 and O-centred organoboronic acid radicals followed by the formation of an O-N bond via combination of the said radicals. Finally transfer of the NO2 group to the aryl moiety occurs through 1,3-aryl migration to provide the nitroarenes.

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.

ELECTROPHILIC TETRAALKYLAMMONIUM NITRATE NITRATION. I. CONVENIENT NEW ANHYDROUS NITRONIUM TRIFLATE SYNTHESIS AND IN-SITU HETEROCYCLIC N-NITRATION

Keywords: Anhydrous Nitration, Nitronium Triflate, Tetrabutylammonium Nitrate, Triflic Anhydride Reaction of tetra-n-butylammonium nitrate and triflic anhydride, CF3SO2OSO2CF3 (Tf2O), in dichloromethane (CH2Cl2) solvent at 0 degrees C, produces anhydrous nitronium nitrate, NO2OSO2CF3 (NO2OTf).Subsequent introduction of various heterocycles and their N-acetylated analogs yield N-nitrated products in 20-76 percent yield with an overall one-pot procedure.

A Convenient Method For N-Nitration Using Ammonium Nitrate/Trifluoroacetic Anhydride

A mixture of ammonium nitrate and trifluoroacetic anhydride is found to be a convenient reagent for N-nitration in the synthesis of nitramines, nitramides, and nitrimides.Yields are comparable to those from conventional, but less convenient or safe, nitrating reagents.