3156-43-2

Usage

Uses

Used in Chemical Synthesis Industry:
TRANS-2-HYDROXY-BETA-NITROSTYRENE 97 is used as a reactant for Michael-acetalization reactions, enabling the formation of acetal compounds that are valuable in the synthesis of complex organic molecules and pharmaceuticals.
Used in Organic Chemistry Research:
In the field of organic chemistry, TRANS-2-HYDROXY-BETA-NITROSTYRENE 97 is used as a reactant for organocatalytic stereoselective Baylis-Hillman-type reactions with Hagemann's esters. This application is crucial for the development of enantioselective synthetic methods and the creation of chiral molecules with potential applications in pharmaceuticals and agrochemicals.
Used in Green Chemistry:
TRANS-2-HYDROXY-BETA-NITROSTYRENE 97 is utilized in catalyst-free aqueous-mediated conjugate addition reactions, which is an environmentally friendly approach to chemical synthesis. This method reduces the need for hazardous catalysts and solvents, making it a preferred choice for green chemistry practices.

InChI:InChI=1/C8H7NO3/c10-8-4-2-1-3-7(8)5-6-9(11)12/h1-6,10H

Upstream product

• 75-52-5 nitromethane 
• 90-02-8 salicylaldehyde 
• 89-95-2 2-methyl-benzyl alcohol 
• 1629184-90-2 (E)-2-[1-(2-hydroxybenzylideneamino)-2-nitroethyl]phenol 
• 67-56-1 methanol 

Downstream Products

• 2963-66-8 2-(2'-Hydroxyphenyl)benzimidazole 

Relevant academic research and scientific papers

Catalytic activity of copper(II) benzenetricarboxylate (HKUST-1) in reactions of aromatic aldehydes condensation with nitromethane: Kinetic and diffusion study

Catalytic activity of copper(II) 1,3,5-benzenetricarboxylate, HKUST-1, in reactions of condensation of aromatic aldehydes with nitromethane was studied. It was shown that HKUST-1 catalyzed condensation of salicylaldehyde with nitromethane leading to formation of trans-nitrovinylphenol, while 9-anthracenecarbaldehyde did not react in the same conditions. Catalytic activity of HKUST-1 was consistent with its sorption capacity in respect to the reagents. The difference in catalytic activity of HKUST-1 in reactions with salicylaldehyde and 9-anthracenecarbaldehyde can be caused by sieving effect (molecules discrimination by size). Kinetics of salicylaldehyde condensation with nitromethane, catalyzed by HKUST-1, as well as kinetics of salicylaldehyde sorption by HKUST-1 were studied. Accessibility of pores of HKUST-1 to salicylaldehyde and condensation product (trans-nitrovinylphenol) was evaluated by molecular mechanics. Catalytic activity (reaction rate and salicylaldehyde diffusion rate) of HKUST-1 is compared with FeIII analog, role of diffusion rate is shown.

Synthesis, characterization and crystal structure of trans-2-(2- Hydroxyphenyl)-1-nitroethylene

The nitroalkene compound, namely trans-2-(2-hydroxyphenyl)-1-nitroethylene (I), has been successfully synthesized from the condensation of 2-hydroxybenzaladehyde with nitromethane. It was characterized by elemental analysis, 1H NMR spectrum and single-cry

Synthesis, crystal structure, and physicochemical properties of the new metal-organic framework - The iron(III) complex with benzene- 1,3,5-tricarboxylate

A new iron(III) coordination compound with the benzene- 1,3,5-tricarboxylate anion of the composition [FeIII2(OH)0.3(H2O)1.7(btc)4/3]Cl1.7· 2.8DMF·1.9H2O (1) was synthesized. Its crystal structure was determined, and the M ? ssbauer spectra were analyzed. The adsorption of salicylaldehyde and nitromethane by compound 1 was studied. The adsorption kinetics of salicylaldehyde is described by the pseudo-second order equation. The diffusion of this aldehyde in particles of compound 1 is, most probably, the rate-limiting step in the Henry reaction.

Green sustainable approach for carbon–carbon bond-forming reactions using FeNPs/DETA@rGO nano-catalyst

We have fabricated eccentric highly persuasive bifunctional FeNPs/DETA@rGO (where DETA = diethylenetriamine) nano-catalyst with a dual activation mechanism by presenting aliphatic amine on the basal and/or edges sites offering a base characteristic and Fe

Regio- and Stereoselective Cascade of β,γ-Unsaturated Ketones by Dipeptided Phosphonium Salt Catalysis: Stereospecific Construction of Dihydrofuro-Fused [2,3-b] Skeletons

Chiral (dihydro)furo-fused heterocycles are significant structural motifs in numerous natural products, functional materials and pharmaceuticals. Therefore, developing efficient methods for preparing compounds with these privileged scaffolds is an important endeavor in synthetic chemistry. Herein, we develop an effective, modular method by a dipeptide-phosphonium salt-catalyzed regio- and stereoselective cascade reaction of readily available linear β,γ-unsaturated ketones with aromatic alkenes, affording a wide variety of structurally fused heterocyclic molecules in high yields with excellent stereoselectivities. Moreover, mechanistic investigations revealed that the bifunctional phosphonium salt controlled the regio- and stereoselectivities of this cascade reaction, particularly proceeding through the initial ketone α-addition followed by O-participated substitution; and the multiple hydrogen-bonding interactions between Br?nsted acid moieties of catalyst and nitro group of aromatic alkene were crucial in asymmetric induction. Given the generality, versatility, and high efficiency of this method, we anticipate that it will have broad synthetic utilities.

Strategies towards potent trypanocidal drugs: Application of Rh-catalyzed [2?+?2?+?2] cycloadditions, sulfonyl phthalide annulation and nitroalkene reactions for the synthesis of substituted quinones and their evaluation against Trypanosoma cruzi

Rhodium-catalyzed [2 + 2 + 2] cycloadditions, sulfonyl phthalide annulations and nitroalkene reactions have been employed for the synthesis of 56 quinone-based compounds. These were evaluated against Trypanosoma cruzi, the parasite that causes Chagas disease. The reactions described here are part of a program that aims to utilize modern, versatile and efficient synthetic methods for the one or two step preparation of trypanocidal compounds. We have identified 9 compounds with potent activity against the parasite; 3 of these were 30-fold more potent than benznidazole (Bz), a drug used for the treatment of Chagas disease. This article provides a comprehensive outline of reactions involving over 120 compounds aimed at the discovery of new quinone-based frameworks with activity against T. cruzi.

Facile synthesis of chiral [2,3]-fused hydrobenzofuran: Via asymmetric Cu(i)-catalyzed dearomative 1,3-dipolar cycloaddition

Intermolecular asymmetric dearomative 1,3-dipolar cycloaddition of 2-nitrobenzofurans with azomethine ylides was enabled by using a chiral Cu(i)/(S,Sp)-iPr-Phosferrox catalyst. As a result, a series of highly stereoselective chiral [2,3]-fused hydrobenzofurans possessing four contiguous stereogenic centers were obtained with good to high yields, diastereoselectivities and enantioselectivities. The reaction has broad substrate scope tolerating various functional groups.

Enantioselective dearomative [3+2] cycloaddition of 2-nitrobenzofurans with aldehyde-derived Morita-Baylis-Hillman carbonates

The phosphine-catalyzed asymmetric dearomative [3+2] cycloaddition of 2-nitrobenzofurans with aldehyde-derived Morita-Baylis-Hillman (MBH) carbonates or allenoate was developed. The reaction with MBH carbonates resulted in a series of cyclopentabenzofurans containing three contiguous stereocenters with good to high yields, diastereoselectivities and enantioselectivities. The use of allenoate also gave the target product with moderate enantioselectivity.

Phosphine-Catalyzed Enantioselective Dearomative [3+2]-Cycloaddition of 3-Nitroindoles and 2-Nitrobenzofurans

Over the past years, the metal-catalyzed dearomative cycloaddition of 3-nitroindoles and 2-nitrobenzofurans have emerged as a powerful protocol to construct chiral fused heterocyclic rings. However, organocatalytic dearomative reaction of these two classe

Synthesis, antiproliferative and pro-apoptotic effects of nitrostyrenes and related compounds in Burkitt’s lymphoma

Background: Cancers of the lymphatic cells (lymphomas) account for approximately 12% of malignant diseases worldwide. The nitrostyrene scaffold is identified as a lead target structure for the development of particularly effective compounds targeting Burkitt’s lymphoma (BL). Objectives: The aims of the curent study were to synthesise a panel of nitrostyrene compounds and to evaluate their activity in Burkitt’s lymphoma (BL). Methods: A panel of structurally varied compounds were designed and synthesised using Henry Knoevenagel condensation reactions. Single crystal X-Ray analysis confirmed the E configuration for six examples of these novel structures. A number of nitrostyrene-related compounds were also investigated including 1,3-bis(aryl)-2-nitropropenes together with heterocyclic scaffolds containing the nitrovinyl pharmacophore such as 3-nitro-2-phenyl-2H-chromenes. The antiproliferative activities of the compounds were evaluated using the BL cell lines EBV- MUTU-1 and EBV+ DG-75 (chemoresistant) to establish preliminary structure-activity relationships. Results: Lead compounds with optimized nitrostyrene scaffolds and 3-nitro-2-phenyl-2Hchromene structures were successfully established with typical IC50 values of 0.45 μM and 0.47 μM in MUTU-1 cells and 1.41 μM and 1.92 μM, respectively, in DG-75 cells. The mechanism of cell death was identified as apoptotic and the lead compound was found to elicit comparable apoptotic effects to Taxol in Burkitt’s lymphoma cell lines MUTU-1 and DG-75. Conclusion: This class of pharmaceutically active compounds with potential for the treatment of Burkitt’s lymphoma suggest a potential role for nitrostyrene based agents in chemotherapy.