39220-93-4

Upstream product

• 5447-97-2 2-bromo-2-nitropropane 
• 555-16-8 4-nitrobenzaldehdye 
• 79-46-9 2-nitropropane 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 100-14-1 4-nitrobenzyl chloride 
• 3958-63-2 lithium 2-nitropropane 

Downstream Products

• 72511-04-7 2-Methyl-2,4'-dinitropropiophenon 
• 1114451-72-7 (R)-2-methyl-2-nitro-1-(4-nitrophenyl)propyl acetate 
• 55605-26-0 2-methyl-2-nitro-1-(4-nitrophenyl)propyl acetate 
• 62557-99-7 Methanesulfonic acid 2-methyl-1-(4-nitro-phenyl)-propenyl ester 
• 79-46-9 2-nitropropane 
• 555-16-8 4-nitrobenzaldehdye 
• 57187-17-4 Methanesulfonic acid 2-methyl-2-nitro-1-(4-nitro-phenyl)-propyl ester 
• 69240-31-9 1-Bromo-2-methyl-2-nitro-1-p-nitrophenylpropan 
• 55605-31-7 1-Chloro-2-methyl-2-nitro-(1-p-nitrophenyl)propan 

Relevant academic research and scientific papers

Nitronate anion recognition and modulation of ambident reactivity by hydrogen-bonding receptors

Nitronate anions were shown to form complexes in DMSO with hydrogen-bonding receptors such as 1,3-dimethylthiourea 1 (Ka = 120M-1) and bicyclic guanidinium2 (Ka = 3200M-1). A ditopic bis-thiourea exhibited increased association with substrates, that contained either two nitronates (Ka = 7000M-1) or a combination of nitronate and carboxylate (Ka = 1200M-1). Complexation of nitronate resulted in a change in the ambident reactivity during alkylation with p-nitrobenzyl bromide. The predominant reaction pathway was shifted from oxygen alkylation to carbon alkylation as receptor binding strength increased. Kinetic analysis indicated an overall inhibition of nitronate reactivity, and this suggests that greater suppression of the oxygen pathway allows carbon alkylation to predominate.

Polymer supported DMAP: An easily recyclable organocatalyst for highly atom-economical Henry reaction under solvent-free conditions

Polymer supported catalysts are regarded as a borderline class of catalysts, which retains the advantages of homogeneous catalysts while securing the ease of recovery by simple filtration and workup of heterogeneous systems. Additionally, such catalysts are less hygroscopic due to the long polymer backbone. Here we have demonstrated that a catalytic amount of polymer supported DMAP (10 mol%) can lead to excellent conversion of an equimolar mixture of aldehyde and nitroalkane exclusively into β-nitroalcohols via the Henry reaction. Unlike most of the commonly used catalysts, polymer supported DMAP can be recovered by simple filtration and reused several times, thereby reducing the operational cost. High synthetic efficiency, total atom economy, near quantitative yields, mild reaction conditions, operational simplicity, easy recovery and reusability of the catalyst, solvent-free reaction conditions and avoidance of traditional reaction workup make the protocol highly significant from Green and Sustainable Chemistry perspectives.

Ethyl acrylate conjugated polystyryl-diphenylphosphine - An extremely efficient catalyst for Henry reaction under solvent-free conditions (SolFC)

Over the last few decades, the fast-growing development of polymer supported reagents has led to the synthesis of a variety of reagents on solid support. Some of the major advantages of using such reagents are that they are less hygroscopic, easy to recover, and can be recycled. Here, we have demonstrated that in situ generated ethyl acrylate conjugated polystyryl-diphenylphosphine (PDPP-EA) derived from the reaction of a mixture of polystyryl-diphenylphosphine and ethyl acrylate in a stoichiometric ratio can efficiently catalyze the synthesis of β-nitroalcohols from the reaction of aldehydes and nitroalkanes under solvent-free conditions (SolFC).

Indium-mediated reaction of 1-bromo-1-nitroalkanes with aldehydes: Access to 2-nitroalkan-1-ols

A novel method for the preparation of 2-nitroalkan-1-ols by an indium-promoted reaction of bromonitromethane with a variety of aldehydes is reported. The reaction was also performed with 2-bromo-2-nitropropanes to afford 2,2-dialkyl-2-nitroalkan-1-ols. The use of chiral sugar-derived aldehydes furnished the corresponding 2-nitroalkan-1-ols with excellent stereoselectivity. The utility of the novel sugar-derived 2,2-dialkyl-2-nitroalkan-1-ols for the preparation of branched iminosugar derivatives was demonstrated by the preparation of a hydroxymethyl branched polyhydroxylated azepane.

Direct asymmetric dynamic kinetic resolution by combined lipase catalysis and nitroaldol (Henry) reaction

The asymmetric synthesis of β-nitroalkanol derivatives was simply achieved by a combined nitroaldol (Henry) reaction with lipase-catalyzed transesterification in high yield and enantiomeric purity (up to 92% and 99% ee) through a direct one-pot procedure.

Tandem Hass-Bender/Henry reaction for the synthesis of dimethylnitro alcohols from benzylic halides

Dimethylnitro alcohols are constructed in a one-pot process from benzylic halides and 2-nitropropane. The use of tetrabutylammonium fluoride (TBAF) as the promoter is essential for this tandem Hass-Bender/Henry reaction to proceed.