5153-68-4

Usage

Uses

Used in Pharmaceutical Industry:
TRANS-4-METHYL-BETA-NITROSTYRENE is used as an organic intermediate for the synthesis of various pharmaceutical compounds. Its unique structure makes it a valuable component in the development of new drugs and medications.
Used in Chemical Synthesis:
TRANS-4-METHYL-BETA-NITROSTYRENE is used as a reagent in the synthesis of N-benzylpyrrolomorphinans, a class of compounds with potential applications in various fields. Its asymmetric Michael addition with benzaldehyde in the presence of silylated pyrrolidine catalyst has been reported, showcasing its versatility in chemical reactions.
Additionally, the hydrogenation of TRANS-4-METHYL-BETA-NITROSTYRENE in the presence of Pd(II) complexes of (Z)-2-((quinolin-3-ylimino)methyl)phenol as catalyst has been studied, further demonstrating its utility in chemical synthesis processes.

InChI:InChI=1/C9H9NO2/c1-8-2-4-9(5-3-8)6-7-10(11)12/h2-7H,1H3/b7-6+

Upstream product

• 75-52-5 nitromethane 
• 104-87-0 4-methyl-benzaldehyde 
• 135711-34-1 Butyl-(2-nitro-1-p-tolyl-ethyl)-amine 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 30669-07-9 4-methoxy-N-[(4-methylphenyl)methylidene]aniline 
• 1355229-73-0 5-(4-methylphenyl)-2-[1-(4-methylphenyl)-2-nitroethoxy]-1,2-oxazolidine-3,3-dicarbonitrile 
• 28691-43-2 1-(4-methylphenyl)-2-nitroethanol 
• 930-88-1 N-methylmaleimide 
• 625-75-2 nitroacetic acid 
• 1866-39-3 trans-p-methylcinnamic acid 
• 3156-37-4 (E)-1-bromo-4-(2-nitrovinyl)benzene 
• 99696-01-2 p-trifluoromethyl-trans-β-nitrostyrene 
• 589-18-4 4-Methylbenzyl alcohol 
• 79-24-3 Nitroethane 

Downstream Products

• 1304774-66-0 C₁₆H₂₁NO₃ 
• 1283189-25-2 2-acetyl-N-(2,4-dichlorophenyl)-4-nitro-3-p-tolylbutanamide 
• 99391-22-7 l-2-<1-(4-methylphenyl)-2-nitroethyl>-cyclohexanone 
• 99391-22-7 u-2-<1-(4-methylphenyl)-2-nitroethyl>-cyclohexanone 
• 1398093-96-3 C₂₆H₂₅ClN₂O₄ 
• 1436787-01-7 (1R,2S,3R,4R,4aS,8aS)-8a-hydroxy-3-nitro-2-phenyl-4-(p-tolyl)decahydronaphthalene-1-carbaldehyde 
• 1288984-88-2 (1R,2S,3S,4R,4aS,8aS)-8a-hydroxy-3-nitro-2-phenyl-4-(p-tolyl)decahydronaphthalene-1-carbaldehyde 
• 1436786-97-8 (2R,3R,4S,4aR)-3-nitro-2-phenyl-4-(p-tolyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-1-carbaldehyde 
• 1436787-05-1 (2R,3S,4S,4aR)-3-nitro-2-phenyl-4-(p-tolyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-1-carbaldehyde 
• 1436787-40-4 (1R,2S,3S,4R,4aS,8aS)-8a-hydroxy-3-nitro-2-(4-nitrophenyl)-4-(p-tolyl)decahydronaphthalene-1-carbaldehyde 
• 1436787-48-2 (1R,2S,3R,4R,4aS,8aS)-8a-hydroxy-3-nitro-2-(4-nitrophenyl)-4-(p-tolyl)decahydronaphthalene-1-carbaldehyde 
• 1436787-44-8 (2R,3R,4S,4aR)-3-nitro-2-(4-nitrophenyl)-4-(p-tolyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-1-carbaldehyde 
• 1436787-52-8 (2R,3S,4S,4aR)-3-nitro-2-(4-nitrophenyl)-4-(p-tolyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-1-carbaldehyde 
• 1431709-11-3 (2E,3E)-4-(phenylsulfonyl)-1-p-tolylbut-3-en-2-one oxime 

Relevant academic research and scientific papers

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

Active Base Hybrid Organosilica Materials based on Pyrrolidine Builder Units for Fine Chemicals Production

The catalytic activity of “pyrrolidine type” fragments included or anchored in the mesoporous silica supports or polymeric frameworks have been fully reported for enantioselective transformation. Nevertheless, low attention was focused on their catalytic abilities to perform base-catalyzed reaction. Accordingly, hybrid materials including pyrrolidine fragments in the mesoporous silica supports were prepared following different synthesis methods, such as micellar and fluoride sol-gel routes in absence of structural directing agents. Their great catalytic performance was explored for various base-catalyzed reactions to the formation of C?C bond through Knoevenagel, Claisen-Schmidt and Henry condensations under microwave irradiation. The benefits of microwave irradiation combined with suitable catalytic properties of pyrrolidine hybrid materials with strong base sites and high accessibility to active centers, allowed carrying out successfully base-catalyzed condensation reactions for the production of fine chemicals. Moreover, the hybrid catalyst exhibited high selectivity and good stability over different catalytic cycles contributing to environmental sustainability.

Organocatalytic Asymmetric Synthesis of Aza-Spirooxindoles via Michael/Friedel-Crafts Cascade Reaction of 1,3-Nitroenynes and 3-Pyrrolyloxindoles

An asymmetric [3+3] cyclization of nitroenynes and 3-pyrrolyloxindoles has been realized with a chiral bifunctional squaramide catalyst. This Michael/Friedel-Crafts cascade strategy provides a facile and efficient access to enantioenriched polycyclic aza-spirooxindoles with 32-95% isolated yields and excellent stereocontrol under mild reaction conditions.

Four-Step Domino Reaction Enables Fully Controlled Non-Statistical Synthesis of Hexaarylbenzene with Six Different Aryl Groups**

Hexaarylbenzene (HAB) derivatives are versatile aromatic systems playing a significant role as chromophores, liquid crystalline materials, molecular receptors, molecular-scale devices, organic light-emitting diodes and candidates for organic electronics. Statistical synthesis of simple symmetrical HABs is known via cyclotrimerization or Diels–Alder reactions. By contrast, the synthesis of more complex, asymmetrical systems, and without involvement of statistical steps, remains an unsolved problem. Here we present a generally applicable synthetic strategy to access asymmetrical HAB via an atom-economical and high-yielding metal-free four-step domino reaction using nitrostyrenes and α,α-dicyanoolefins as easily available starting materials. Resulting domino product—functionalized triarylbenzene (TAB)—can be used as a key starting compound to furnish asymmetrically substituted hexaarylbenzenes in high overall yield and without involvement of statistical steps. This straightforward domino process represents a distinct approach to create diverse and still unexplored HAB scaffolds, containing six different aromatic rings around central benzene core.

Catalytic Asymmetric Construction of Tertiary Carbon Centers Featuring an α-Difluoromethyl Group with CF2H-CH2-NH2as the "building Block"

We report here for the first time a novel difluoromethylated ketimine building block condensed by thioisatin and difluoroethylamine, offering efficient access to a broad range of enantioenriched products bearing difluoroethylamine units (27 examples, ≤98% yield, >99% ee) in the presence of quinine-derived squaramide. Further transformation of the intermediate would generate a variety of versatile functional blocks like α-difluoromethyl amines, β-amino acid, and β-diamine with retention of the enantiomeric excess at the difluoromethyl-bound carbon.

Skeletally Tunable Seven-Membered-Ring Fused Pyrroles

We describe a copper-mediated method that enables the synthesis of seven-membered-ring fused pyrroles (7-mrFPs). The protocol proceeds via an in situ spiro-intermediate ring expansion and tolerates a library of 7-mrFP derivatives with a broad range of functional groups in a simple step with tangible parameters and substrate adaptations. These rare 7-mrFPs are now accessible on a millimolar scale, and selected examples exhibit high antioxidant activity.

Co-Polymeric Nanosponges from Cellulose Biomass as Heterogeneous Catalysts for amine-catalyzed Organic Reactions

Heterogeneous catalysts prepared from biomass waste sources are attracting increasing interest. The reasons rely on the possibility of combining the virtuous approach of circular economy with the consolidated advantages of heterogeneous catalysis, namely the recycling of the system and the possibility to drive selectivity towards desired products. Herein we report a highly porous cellulose-based nanosponge (CNS) and its use as a recoverable catalyst for Henry and Knoevenagel reactions, two classical amino-catalyzed transformations. The material is obtained by cross-linking between TEMPO-oxidized cellulose nanofibers (TOCNF) and branched polyethyleneimine 25 kDa (bPEI) in the presence of citric acid. CNS have been developed as sorbent materials for water remediation but their use as heterogeneous catalysts was never investigated. The fully characterized micro- and nano-porous system guarantees a complete penetration of CNS, allowing reagents to diffuse within. Indeed, by modulating reaction conditions (catalyst loading, temperature, solvent, microwave versus conventional heating, relative ratio of reagents) it was possible to drive selectivity towards the desired products, while maintaining high efficiency in terms of conversion. The catalyst could be re-used several times without losing in catalytic efficiency. In most cases the products’ distribution is quite different from homogeneous conditions, this much more emphasizing the importance of this heterogeneous solution.

Porous Boron Nitride as a Weak Solid Base Catalyst

Porous boron nitride was synthesized by pyrolysis from boric acid and urea mixed in varying molar ratios. The boron nitride prepared had high surface areas ranging from 376 to 647 m2 g?1 with both microporous and mesoporous structures. The sample prepared with a urea-to-boric acid molar ratio of 5 exhibited the highest pore volume with the highest surface area of mesopores. Boron-K edge X-ray absorption fine structure spectroscopy revealed that the surface structure consisted of BN3 sites along with BN2O, BNO2, and BO3 sites. Fourier transform infrared (FTIR) spectroscopy indicated the formation of amino and hydroxyl groups on the surface. Analysis using color indicator reagents and deuterated chloroform-adsorbed FTIR results indicated that the porous boron nitride had very weak base sites of strength +7.2>H?≥+6.3. Porous boron nitride exhibited a high activity for the nitroaldol reaction with a high selectivity for nitroalkene (>97 %). A good correlation was observed between the catalytic activity of the boron nitride catalysts and their porous structures.

Heteroannulation of Alkenes with Enynyl Benziodoxolones and Silver Nitrite Involving CC bond Oxidative Cleavage: Entry to 3-Aryl-?2-isoxazolines

A copper-catalyzed [2 + 2 + 1] heteroannulation of alkenes with enynyl benziodoxolones and AgNO2 involving oxidative cleavage of the CC bond promoted by cooperative Zn(OTf)2, KOAc, and 4 ? MS for producing 3-aryl δ2-isoxazolines is reported. Mechanistic s