60947-52-6

Usage

Uses

Used in Dye and Pigment Production:
DNPB is utilized as a key intermediate in the synthesis of dyes and pigments, contributing to the vibrant coloration and stability of these products in various applications.
Used in Pharmaceutical Manufacturing:
In the pharmaceutical industry, DNPB serves as a crucial component in the production of certain medications, highlighting its importance in the development of healthcare solutions.
Used in Organic Synthesis:
DNPB is employed as a versatile chemical intermediate in organic synthesis, enabling the creation of a wide range of organic compounds for diverse applications.
Used in Chemical Intermediates:
As a chemical intermediate, DNPB plays a significant role in the synthesis of other complex chemical compounds, facilitating advancements in the chemical industry.

Upstream product

• 102-96-5 (2-nitroethenyl)benzene 
• 6125-24-2 2-Phenylnitroethane 
• 75-52-5 nitromethane 
• 134-81-6 benzil 
• 103-63-9 1-phenyl-2-bromoethane 
• 5153-67-3 nitrostyrene 
• 60-29-7 diethyl ether 
• 64-19-7 acetic acid 
• 7647-01-0 hydrogenchloride 

Relevant academic research and scientific papers

Cathodic hydrodimerization of nitroolefins

Nitroalkenes are easily accessible in high variety by condensation of aldehydes with aliphatic nitroalkanes. They belong to the group of activated alkenes that can be hydrodimerized by cathodic reduction. There are many olefins with different electron withdrawing groups used for cathodic hydrodimerization, but not much is known about the behaviour of the nitro group. Synthetic applications of this group could profit from the easy access to nitroolefins in large variety, the C-C bond formation with the introduction of two nitro groups in a 1,4-distance and the conversions of the nitro group by reduction to oximes and amines, the conversion into aldehydes and ketones via the Nef reaction and base catalyzed condensations at the acidic CH bond. Eight 1-aryl-2-nitro-1-propenes have been electrolyzed in an undivided electrolysis cell to afford 2,5-dinitro-3,4-diaryl hexanes in high yield. The 4-methoxy-, 4-trifluoromethyl-, 2-chloro- and 2,6-difluorophenyl group and furthermore the 2-furyl and 2-pyrrolyl group have been applied. The reaction is chemoselective as only the double bond but not the nitro group undergoes reaction, is regioselective as a β,β-coupling with regard to the nitro group and forms preferentially two out of six possible diastereomers as major products.

N -heterocyclic carbene organocatalytic reductive β,β-coupling reactions of nitroalkenes via radical intermediates

An unprecedented N-heterocyclic carbene catalytic reductive β,β-carbon coupling of α,β-nitroalkenes, by using an organic substrate to mimic the one-electron oxidation role of the pyruvate ferredoxin oxidoreductase (PFOR) in living systems, has been develo

Instantaneous SmI2/H2O/amine mediated reduction of nitroalkanes and α,β-unsaturated nitroalkenes

A rapid method for efficient reduction of nitroalkanes and α,β-unsaturated nitroalkenes using SmI2/H2O/amine has been developed.

Additions of organomanganese reagents to conjugated nitroolefins

Additions of organomanganese reagents to aromatic and aliphatic conjugated nitroolefins were examined for the first time. In most cases reaction proceeded rapidly at -30°C. Unlike Mn reagents lacking β-hydrogens (Me, Ph), which lead to oxidative coupling and reductive dimerisation of nitrostyrenes, benzylmanganese chloride gives 1,4-addition in yields exceeding Grignard or Cu-assisted additions. At 0°C alkyl(Bu, Pr)-manganese reagents undergo an addition-migration-elimination process with nitrostyrenes providing a convenient and stereospecific entry into arylated trans-olefins.

Titanium(III) Chloride Mediated Reduction of 1-Nitro-2-phenylethenes

The reaction of 1-nitro-2-phenylethenes (β-nitrostyrenes) with aqueous titanium(III) chloride afforded substituted pyrroles in addition to the expected reduction products, oximes and carbonyl compounds. 2-Substituted 1-nitro-2-phenylethenes yielded divinylamine derivatives instead of pyrroles.The reaction mechanism has been rationalized by taking account of the electron transfer from titanium(III) species to the nitro olefines, followed by protonation, dimerization, cyclization, and/or hydrolysis.

TITANIUM TRICHLORIDE MEDIATED REDUCTION OF NITROSTYRENES

Reactions of substituted nitrostyrenes with aqueous titanium trichloride afforded pyrroles, carbonyl compounds, and oximes.In some instances, divinylamines were produced as well.The reaction mechanism is rationalized taking account of electron transfer to nitroethylenes from Ti(III), followed by protonation, dimerization, cyclization, and hydrolysis.