3179-08-6

Usage

Uses

Used in Organic Synthesis:
4-HYDROXY-B-NITROSTYRENE is used as a building block in the synthesis of various organic molecules, leveraging its strong electron-withdrawing and -donating properties to facilitate a range of chemical reactions.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 4-HYDROXY-B-NITROSTYRENE is utilized for its potential applications in the development of new pharmaceutical compounds, given its reactivity as a Michael acceptor and its possible biological activity.
Used in Pharmaceutical Industry:
4-HYDROXY-B-NITROSTYRENE is of interest to researchers in the pharmaceutical industry due to its potential as a precursor in the synthesis of bioactive molecules and its possible direct involvement in drug discovery efforts.
Used in Research and Development:
4-HYDROXY-B-NITROSTYRENE is employed in research and development settings to explore its potential as a Michael acceptor in organic reactions, which could lead to the creation of new chemical entities with therapeutic potential.

InChI:InChI=1/C8H7NO3/c10-8-3-1-7(2-4-8)5-6-9(11)12/h1-6,10H/b6-5+

Upstream product

• 18984-24-2 4-acetoxy-β-nitro-styrene 
• 75-52-5 nitromethane 
• 123-08-0 4-hydroxy-benzaldehyde 
• 7400-08-0 para-coumaric acid 
• 123-11-5 4-methoxy-benzaldehyde 
• 555-16-8 4-nitrobenzaldehdye 
• 5736-88-9 p-butoxybenzaldehyde 
• 104-87-0 4-methyl-benzaldehyde 
• 878-00-2 4-formylphenyl acetate 

Downstream Products

• 107496-10-6 Phosphoric acid diethyl ester 4-((E)-2-nitro-vinyl)-phenyl ester 
• 107496-07-1 Toluene-4-sulfonic acid 4-((E)-2-nitro-vinyl)-phenyl ester 
• 50368-65-5 5-(4-hydroxy-phenyl)-3-methyl-2-thioxo-[1,3,4]thiadiazinan-6-one O-ethoxycarbonyl-oxime 
• 1228935-44-1 ethyl 5-(hydroxyimino)-4-(4-hydroxyphenyl)-2-(trifluoromethyl)-2,5-dihydrofuran-3-carboxylate 
• 1228935-52-1 ethyl 2-hydroxy-4-(4-hydroxyphenyl)-5-imino-2-(trifluoromethyl)-2,5-dihydrofuran-3-carboxylate 
• 1294505-75-1 C₁₁H₁₃NO₄ 
• 1607020-70-1 4-(1-benzyl-1H-1,2,3-triazol-5-yl)phenol 
• 6265-55-0 2-(4-hydroxyphenyl)benzothiazole 
• 89221-21-6 4-(4-hydroxyphenyl)-1,2,3-triazole 
• 18984-24-2 4-acetoxy-β-nitro-styrene 

Relevant academic research and scientific papers

Efficient bifunctional nanocatalysts by simple postgrafting of spatially isolated catalytic groups on mesoporous materials

(Chemical Equation Presented) Hard graft pays off for Henry: An efficient acid-base bifunctional mesoporous catalyst was prepared by one-step post-synthesis grafting of aminoorganoalkoxysilane groups on mesoporous silica (see picture). The catalyst led to

Synthesis of functionalized carbon microspheres and their catalyst activity in C—O and C—N bond formation reactions

Disclosed herein is a simple process for functionalization/grafting of carbon microspheres obtained from bagasse with various active functional groups onto it and use of the same as catalyst for various organic reactions, having very high selectivity and conversion rate.

Access to C5-Alkylated Indolines/Indoles via Michael-Type Friedel-Crafts Alkylation Using Aryl-Nitroolefins

A straightforward synthetic route toward C5-alkylated indolines/indoles has been developed. The strategy is composed of Zn(OTf)2-catalyzed Friedel-Crafts alkylation of N-benzylindolines with nitroolefins, and a series of diverse indolines was first obtained in up to 99% yield. This reaction provides a direct and practical route to a variety of the C5-alkylated indolines which were also utilized for accessing corresponding indoles. Indoline derivatives with free NH groups could be obtained through an N-deprotection reaction. Moreover, the primary alkyl nitro groups in both indolines and indoles are amenable to further synthetic elaborations, thereby broadening the diversity of the products.

Zeolite Y-assisted nitration of aromatic and heterocyclic compounds and decarboxylative nitration of α,β-unsaturated acids under non-conventional conditions

Zeolite Y was found to be an efficient catalyst for a facile nitration of aromatic compounds with acetonitrile as the solvent in the presence of small amounts of HNO3 at room temperature. The reactions afforded mono-nitro derivatives of aromatic compounds in about three hours under stirred conditions with high yields and regioselectivity. The reaction times drastically reduced to about 20 min under sonication and to about 20 s under microwave irradiation. Zeolite is recovered after completion of the reaction and recycled for three to four times without any problem. The approach is particularly appropriate for the conversion of unsaturated cinnamic acids into nitrostyrenes.

METHODS AND COMPOSITIONS FOR SELECTIVE AND TARGETED CANCER THERAPY

Provided herein are methods and compositions for selective and targeted cancer therapy, in particular certain benzothiophenes, benzothiazoles, oxalamides, N-acyl ureas and chromones, and their use in selectively treating certain adenocarcinomas. In some embodiments, the selective toxicity of the compounds may be mediated through SCD1 and/or CYP450 such as CYP4F11.

Ethylenediamine-functionalized magnetic Fe3O4@SiO2 nanoparticles: cooperative trifunctional catalysis for selective synthesis of nitroalkenes

A magnetically separable trifunctional nanocatalyst Fe3O4@SiO2-NH2 was synthesized and characterized by TEM, FT-IR, XRD, TGA, and EA. The designed nanocatalyst was found to be highly active for selective synthesis of nitroalkenes with nitromethane and aromatic aldehyde through cooperative trifunctional catalysis of primary amine, secondary amine and Si-OH groups on the surface of the catalyst. Under the optimized conditions, various representative substrates were extended to obtain the corresponding products in moderate or excellent yields. After the reaction, the trifunctional nanocatalyst was easily recovered and recycled by applying an external magnet. In addition, a possible cooperative trifunctional catalysis mechanism was also proposed.

Ultrasonically Assisted Rate Enhancements in Trichloroisocyanuric Acid/DMF/NaNO2 Triggered Nitration of Aromatic Compounds and Decarboxylative Nitration of α,β-Unsaturated Acids

An efficient and safe method for nitration of aromatic compounds and decarboxylative nitration of α,β-unsaturated acids was developed using trichloroisocyanuric acid (TCICA)/dimethylformamide (DMF) in the presence of NaNO2. The reaction times of conventional protocol reduced from 8-10 h to 1.0-1.5 h (60-90 min) under sonication, even though the yields are comparable under both the conditions.

Ultrasonic and microwave-assisted synthesis of β-nitro styrenes and nitro phenols with tertiary butyl nitrite under acid-free conditions

Tertiary butyl nitrite (TBN) is an acid-free and safe nitrating agent that provides preferentially β-nitrostyrenes with cinnamic acids and corresponding nitro derivatives with phenols in good yields under classical conditions. However, ultrasonic and microwave-assisted reactions reduced the reaction times substantially and enhanced the yields from good to excellent. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.

Oxalylchloride/DMF as an efficient reagent for nitration of aromatic compounds and nitro decarboxylation of cinnamic acids in presence of KNO 3 or NaNO2 under conventional and nonconventional conditions

Nitration of aromatic compounds and cinnamic acids with oxalylchloride/DMF afforded the corresponding nitro derivatives in the presence of KNO3 or NaNO2 under conventional and nonconventional (ultrasonic and microwave) conditions. The present methodology offers several benefits such as excellent yields, simple work-up procedure, and short reaction times. The yields obtained under present methodology are comparable with those obtained from (POCl3/DMF/KNO3 or NaNO2) and (SOCl 2/DMF/KNO3 or NaNO2) systems followed by shorter reaction times. The reaction times of sonication and microwave conditions are very shorter than those of the conventional conditions.

Ambiphilic dual activation role of a task-specific ionic liquid: 2-hydroxyethylammonium formate as a recyclable promoter and medium for the green synthesis of β-nitrostyrenes

A cost-effective task-specific ionic liquid, 2-hydroxyethylammonium formate, efficiently promotes the condensation of nitroalkanes with various aldehydes to produce β-nitrostyrenes in high to excellent yields at room temperature. This reaction does not involve any hazardous organic solvent and toxic catalyst. The ionic liquid is recovered and recycled for subsequent reactions. In addition, a novel mechanism has been proposed invoking ambiphilic dual activation influence of the ionic liquid.