70833-52-2

Usage

Classification

Nitro alcohol

Usage

Precursor for the synthesis of other organic compounds, used in various industrial applications

Physical properties

Colorless to pale yellow liquid, slightly sweet odor, insoluble in water, soluble in organic solvents

Safety concerns

Potential toxic and irritant effects, proper safety guidelines and regulations should be followed to minimize risk of exposure and harm.

InChI:InChI=1/C13H27NO3/c1-2-3-4-5-6-7-8-9-10-11-13(15)12-14(16)17/h13,15H,2-12H2,1H3

Upstream product

• 75-52-5 nitromethane 
• 112-54-9 Dodecanal 

Relevant academic research and scientific papers

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).

Henry reaction in aqueous media at neutral pH

An efficient method for the synthesis of β-nitro alcohols from nitro alkanes and aldehydes in aqueous phosphate buffer under neutral pH conditions at room temperature is reported. In the case of higher nitro alkanes, the reaction showed very good diastereoselectivity to give syn β-nitro alcohols in preference to their anti products. Copyright

Dual hydrogen-bond/enamine catalysis enables a direct enantioselective three-component domino reaction

It takes two to tango: A dual catalyst system, composed of a highly enantioselective enamine catalyst and a multiple-hydrogen-bond catalyst, enabled the chemoselective union of two aldehydes and a nitromethane unit with near-perfect enantioselectivities, excellent diastereoselectivities, and high yields under neutral conditions (see scheme). Copyright

Activation of Peroxisome Proliferator-Activated Receptor γ (PPARγ) by nitroalkene fatty acids: Importance of nitration position and degree of unsaturation

Nitroalkene fatty acids are potent endogenous ligand activators of PPARγ-dependent transcription. Previous studies with the naturally occurring regioisomers of nitrolinoleic acid revealed that the isomers are not equivalent with respect to PPARγ activation. To gain further insight into the structure-activity relationships between nitroalkenes and PPARγ, we examined additional naturally occurring nitroalkenes derived from oleic acid, 9-nitrooleic acid (E-9-NO2-18:1 [1]) and 10-nitrooleic acid (E-10-NO2-18:1 [2]), and several synthetic nitrated enoic fatty acids of variable carbon chain length, double bonds, and nitration site. At submicromolar concentrations, E-12-NO2 derivatives were considerably more potent than isomers nitrated at carbons 5, 6, 9, 10, and 13, and chain length (16 versus 18) or number of double bonds (1 versus 2) was of little consequence for PPARγ activation. Interestingly, at higher concentrations (>2 μM) the nitrated enoic fatty acids (E-9-NO2-18:1 [1], E-9-NO2-16:1 [3], E-10-NO2-18:1 [2], and E-12-NO 2-18:1 [7]) deviated significantly from the saturable pattern of PPARγ activation observed for nitrated 1,4-dienoic fatty acids (E-9-NO2-18:2, E-10-NO2-18:2, E-12-NO2-18:2, and E-13-NO2-18:2).