399-25-7

Usage

Uses

Used in Organic Synthesis:
1-Fluoro-2-(2-nitrovinyl)benzene is used as a key intermediate in the synthesis of various organic compounds. Its unique structure allows for a wide range of chemical reactions, making it a valuable building block in the development of new molecules.
Used in Pharmaceutical Industry:
1-Fluoro-2-(2-nitrovinyl)benzene is used as a starting material for the synthesis of pharmaceutical compounds. Its presence in the molecular structure can impart specific properties to the final drug, such as improved pharmacokinetics, enhanced potency, or reduced side effects.
Used in Agrochemical Industry:
1-Fluoro-2-(2-nitrovinyl)benzene is used as a precursor in the production of agrochemicals, such as pesticides and herbicides. Its incorporation into these compounds can lead to improved efficacy, selectivity, or environmental compatibility.
Safety and Environmental Considerations:
Due to its flammable nature and potential harmful effects if ingested or inhaled, 1-Fluoro-2-(2-nitrovinyl)benzene should be handled with caution. Proper safety measures, including the use of personal protective equipment and adherence to handling and disposal regulations, are essential to minimize risks to human health and the environment. Additionally, its potential environmental impacts should be assessed and managed to ensure sustainable use in various applications.

Upstream product

• 75-52-5 nitromethane 
• 446-52-6 2-Fluorobenzaldehyde 
• 89-99-6 2-fluorobenzylamine 

Downstream Products

• 52721-69-4 [2-(2-fluorophenyl)ethyl]amine 
• 77484-24-3 chloro-3 fluoro-4 indolinone-2 
• 77484-34-5 acide N-acetyl chloro-2 (o.fluorophenyl)-2 acetohydroxamique 
• 77484-44-7 chlorure de l'acide N-acetoxy chloro-2 (o.fluorophenyl)-2 acetohydroximique 
• 1537-27-5 2,2-Bis-<2-nitro-1-(2-fluor-phenyl)-ethyl>-indandion-(1,3) 
• 401-42-3 2-fluoro-5,β-dinitro-styrene 
• 917473-36-0 C₂₄H₃₂FN₃O₅ 
• 1132767-79-3 C₂₀H₁₉FN₂O₄ 
• 1173094-27-3 ethyl 3-(2-fluorophenyl)-4-nitro-1H-pyrrole-2-carboxylate 
• 1173094-30-8 ethyl 4-(2-fluorophenyl)-5-tosyl-1H-pyrrole-3-carboxylate 
• 1201676-71-2 C₁₅H₁₇F₂NO₆ 
• 1228935-47-4 ethyl 4-(2-fluorophenyl)-5-(hydroxyimino)-2-(trifluoromethyl)-2,5-dihydrofuran-3-carboxylate 
• 1228599-99-2 (1R,5R,6S,7R)-6-(2-fluorophenyl)-1-hydroxy-7-nitrobicyclo[3.2.1]octan-8-one 

Relevant academic research and scientific papers

Application of Fluorine- And Nitrogen-Walk Approaches: Defining the Structural and Functional Diversity of 2-Phenylindole Class of Cannabinoid 1 Receptor Positive Allosteric Modulators

Cannabinoid 1 receptor (CB1R) allosteric ligands hold a far-reaching therapeutic promise. We report the application of fluoro- and nitrogen-walk approaches to enhance the drug-like properties of GAT211, a prototype CB1R allosteric agonist-positive allosteric modulator (ago-PAM). Several analogs exhibited improved functional potency (cAMP, β-arrestin 2), metabolic stability, and aqueous solubility. Two key analogs, GAT591 (6r) and GAT593 (6s), exhibited augmented allosteric-agonist and PAM activities in neuronal cultures, improved metabolic stability, and enhanced orthosteric agonist binding (CP55,940). Both analogs also exhibited good analgesic potency in the CFA inflammatory-pain model with longer duration of action over GAT211 while being devoid of adverse cannabimimetic effects. Another analog, GAT592 (9j), exhibited moderate ago-PAM potency and improved aqueous solubility with therapeutic reduction of intraocular pressure in murine glaucoma models. The SAR findings and the enhanced allosteric activity in this class of allosteric modulators were accounted for in our recently developed computational model for CB1R allosteric activation and positive allosteric modulation.

Design, synthesis and evaluation of thiourea derivatives as antimicrobial and antiviral agents

Background: The development of drug-resistant by bacteria appears rapidly and thus making the effectiveness of antibiotics severely limited. Methods: A series of thiourea derivatives was synthesized, characterized and evaluated for their in vitro antibacterial, antifungal and antiviral activities. Results: Structures of the newly synthesized compounds were confirmed by elemental and spectral analysis. The biological results showed that some of the target compounds displayed comparable antimicrobial and antiviral activities with reference drugs. Structure-activity relationship studies revealed that the ortho-chloro or fluoro substituted phenyl at Ar1 and substituted pyridinyl at Ar2 positions of the thiourea nucleus are essential for their in vitro antimicrobial and anti-HIV activity. In particular, compounds 8 and 10 showed better activity against the tested bacteria, fungi and viral strains than other synthesized PET derivatives reported in the present study. Conclusion: These results provide an encouraging lead that could be used for the development of new potent antiviral and antimicrobial agents.

Substrate promiscuity of ortho-naphthoquinone catalyst: Catalytic aerobic amine oxidation protocols to deaminative cross-coupling and n-nitrosation

ortho-Naphthoquinone-based organocatalysts have been identified as versatile aerobic oxidation catalysts. Primary amines were readily cross-coupled with primary nitroalkanes via deaminative pathway to give nitroalkene derivatives in good to excellent yields. Secondary and tertiary amines were inert to ortho-naphthoquinone catalysts; however, secondary nitroalkanes were readily converted by ortho-naphthoquinone catalysts to the corresponding nitrite species that in situ oxidized the amines to the corresponding N-nitroso compounds. Without using harsh oxidants in a stoichiometric amount, the present catalytic aerobic oxidation protocol utilizes the substrate promiscuity feature to provide a facile access to amine oxidation products under mild reaction conditions.

Catalyst-free sulfa-Michael addition of pyrimidine-2-thiol to nitroolefins

Catalyst-free sulfa-Michael addition of pyrimidine-2-thiol to nitroolefins is described. A series of 2-((2-nitro-1-arylethyl)thio)pyrimidines were efficiently synthesized. The protocol has advantages of wide range of substituents tolerance, no catalyst, additives and bases, mild condition, and high yield. The method can also extend to gram scale.

Cooperative Multifunctional Catalysts for Nitrone Synthesis: Platinum Nanoclusters in Amine-Functionalized Metal–Organic Frameworks

Nitrones are key intermediates in organic synthesis and the pharmaceutical industry. The heterogeneous synthesis of nitrones with multifunctional catalysts is extremely attractive but rarely explored. Herein, we report ultrasmall platinum nanoclusters (PtNCs) encapsulated in amine-functionalized Zr metal–organic framework (MOF), UiO-66-NH2 (Pt@UiO-66-NH2) as a multifunctional catalyst in the one-pot tandem synthesis of nitrones. By virtue of the cooperative interplay among the selective hydrogenation activity provided by the ultrasmall PtNCs and Lewis acidity/basicity/nanoconfinement endowed by UiO-66-NH2, Pt@UiO-66-NH2 exhibits remarkable activity and selectivity, in comparison to Pt/carbon, Pt@UiO-66, and Pd@UiO-66-NH2. Pt@UiO-66-NH2 also outperforms Pt nanoparticles supported on the external surface of the same MOF (Pt/UiO-66-NH2). To our knowledge, this work demonstrates the first examples of one-pot synthesis of nitrones using recyclable multifunctional heterogeneous catalysts.

Benzo-hexatomic ring derivative used as DPP-4 inhibitor and application of benzo-hexatomic ring derivative

The invention relates to a benzo-hexatomic ring derivative used as a DPP-4 inhibitor and application of the benzo-hexatomic ring derivative, in particular to compounds shown as in formula I, medicine compositions with the compounds shown as in the formula I and application of the compounds in preparing medicines for treating diseases related to DPP-4 or inhibiting the DPP-4.

Iodine catalyzed one-pot synthesis of highly substituted N-methyl pyrroles via [3 + 2] annulation and their in vitro evaluation as antibacterial agents

A new class of highly substituted pyrroles have been synthesized via a simple, fast, and efficient method using environmentally friendly iodine catalyzed [3 + 2] annulation. N-Methyl-N-[(E)-1-(methylsulfanyl)-2-nitro-1-ethenyl]amine (NMSM) 1 and β-nitrostyrenes 3 underwent cycloaddition to afford the desired products 4 in excellent yields under solvent and metal free conditions. All the pyrrole derivatives were evaluated for their in vitro anti-bacterial activity. Among the synthesized pyrrole derivatives, 4b, 4c, 4e, 4g, 4i, 4j, 4l, 4m and 4n displayed good inhibitory properties against a panel of Gram positive and negative infectious pathogens.

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.

Asymmetric Michael addition of α-fluoro-α-nitroalkanes to nitroolefins: Facile preparation of fluorinated amines and tetrahydropyrimidines

An asymmetric Michael addition of α-fluoro-α-nitroalkanes to nitroolefins was developed, and the products were obtained in good chemical yields and with high stereoselectivities. Highly functionalized adducts provided ready access to fluorinated amines and tetrahydropyrimidines in an optically enriched form.

Highly efficient iridium-catalyzed asymmetric hydrogenation of β-acylamino nitroolefins

The first highly efficient Ir-catalyzed enantioselective hydrogenation of β-acylamino nitroolefins is reported. This reaction provides straightforward access to chiral β-amino nitroalkanes in high yields and excellent enantioselectivities (up to >99.9% ee) catalyzed by an Ir-(R,R)-f-spiroPhos complex. This journal is