28123-72-0

Usage

Uses

Used in Pharmaceutical and Agrochemical Production:
2-(4-Nitrophenyl)furan is used as a reagent in the production of pharmaceuticals and agrochemicals. Its strong nitro group and unique structural properties make it a valuable component in the synthesis of various organic compounds, contributing to the development of new drugs and agricultural chemicals.
Used in Dye and Pigment Manufacturing:
In the dye and pigment industry, 2-(4-Nitrophenyl)furan is utilized for the manufacturing of dyes, pigments, and other specialty chemicals. Its yellow crystalline form and chemical properties contribute to the creation of a wide range of colorants and pigments used in various applications.
Used in Organic Electronics and Materials Science:
2-(4-Nitrophenyl)furan has potential applications in the field of organic electronics and materials science. Its unique structural properties make it a promising candidate for the development of new materials with specific electronic properties, such as in the creation of organic semiconductors and other advanced materials.

Upstream product

• 28123-73-1 5-(4-nitrophenyl)-furan-2-carboxylic acid 
• 586-78-7 para-nitrophenyl bromide 
• 118486-94-5 2-(tributylstannyl)furan 
• 110-00-9 furan 
• 100-01-6 4-nitro-aniline 
• 456-27-9 4-nitrobenzenediazonium tetrafluoroborate 
• 51451-34-4 4-nitrophenyl sulfurofluoridate 
• 1005326-81-7 (E)-4-hydroxy-1-(4-nitrophenyl)but-2-en-1-one 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 13331-23-2 fur-2-ylboronic acid 
• 17763-80-3 para-nitrophenyl triflate 
• 636-98-6 p-nitrobenzene iodide 
• 166328-14-9 potassium (furan-2-yl)trifluoroboranuide 
• 7147-77-5 5-(4-nitrophenyl)-2-furaldehyde 

Downstream Products

• 59147-02-3 4-(furan-2-yl)aniline 
• 898552-69-7 4-{3-[5-(4-nitro-phenyl)-furan-2-yl]-5-thioxo-thiazolo[4,5-c]isothiazol-6-yl}-butyric acid ethyl ester 
• 868755-79-7 2-(4-(furan-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 56297-30-4 2,5-(4′-nitrophenyl)furan 
• 126739-60-4 2-(4′-methoxyphenyl)-5-(4′-nitrophenyl)furan 
• 69836-64-2 N-(4-furan-2-ylphenyl)acetamide 
• 89260-62-8 4-(5-Dimethylaminomethyl-furan-2-yl)-phenylamine 
• 194220-99-0 1-(4-Nitro-phenyl)-7-oxa-bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid dimethyl ester 

Relevant academic research and scientific papers

4-(Furan-2-yl)phenyl-containing polydithienylpyrroles as promising electrodes for high contrast and coloration efficiency electrochromic devices

A 4-(furan-2-yl)phenyl-containing conjugated dithienylpyrrole (FPT) was prepared using a Paal-Knorr reaction and its homologous homopolymer (PFPT) and copolymers (P(FPT-co-DTC) and P(FPT-co-DTP)) were electrosynthesized. Spectroelectrochemical investigations displayed that PFPT film was saffron yellow (0 V) in a reduced state, yellowish-gray (1.0 V), light purple (1.2 V), and bluish-purple (1.4 V) in an oxidized state. P(FPT-co-DTC) film was green, grayish-green, grayish-blue, and bluish-purple from reduced to oxidized states. Electrochromic switching studies revealed the transmittance change (ΔT) of PFPT, P(FPT-co-DTC), and P(FPT-co-DTP) films were 22.7%, 44.8%, and 50.7% at 1320 nm, 906 nm, and 1212 nm, respectively, and the coloration efficiency (η) of PFPT, P(FPT-co-DTC), and P(FPT-co-DTP) films were estimated to be 181.8 cm2 C?1, 229.0 cm2 C?1, and 232.4 cm2 C?1 at 1320 nm, 906 nm, and 1212 nm, respectively. A P(FPT-co-DTP)/PProDOT-Et2 ECD revealed a high ΔT (38.6% at 612 nm) and rapid switching time, whereas a PFPT/PProDOT-Et2 ECD attained a high ΔT (33.3% at 590 nm), a high η (533.5 cm2 C?1 at 590 nm) and long-term reversible redox behaviors.

Pyrazole-Mediated C-H Functionalization of Arene and Heteroarenes for Aryl-(Hetero)aryl Cross-Coupling Reactions

Herein we introduce a transition-metal-free protocol that involves a commercially available, inexpensive pyrazole molecule to conduct C-C cross-coupling reactions at room temperature via a radical pathway. Using this method, an aryldiazonium salt has been coupled to a wide range of arenes and heteroarenes including benzene, mesitylene, thiophene, furan, benzoxazole to result the corresponding biaryl products. The full reaction mechanism is elucidated along with the crystallographic probation of an active initiator species. A potassium-stabilized deprotonated pyrazole steers single-electron transfer to the substrate and behaves as an initiator for the reaction.

Identification of Piperidine-3-carboxamide Derivatives Inducing Senescence-like Phenotype with Antimelanoma Activities

This study evaluated the potential use of senescence-inducing small molecules in the treatment of melanoma. We screened commercially available small-molecule libraries with high-throughput screening and high-content screening image-based technology. Our findings showed an initial hit with the embedded N-arylpiperidine-3-carboxamide scaffold-induced senescence-like phenotypic changes in human melanoma A375 cells without serious cytotoxicity against normal cells. A focused library containing diversely modified analogues were constructed and examined to evaluate the structure-activity relationship of N-arylpiperidine-3-carboxamide derivatives starting from hit 1. This work identified a novel compound with remarkable antiproliferative activity in vitro and demonstrated the key structural moieties within.

σ-Bond initiated generation of aryl radicals from aryl diazonium salts

σ-Bond nucleophiles and molecular oxygen transform aryl diazonium salts into aryl radicals. Experimental and computational studies show that Hantzsch esters transfer hydride to aryl diazonium species, and that oxygen initiates radical fragmentation of the diazene intermediate to produce aryl radicals. The operational simplicity of this addition-fragmentation process for the generation of aryl radicals, by a polar-radical crossover mechanism, has been illustrated in a variety of bond-forming reactions.

UiO-66 microcrystals catalyzed direct arylation of enol acetates and heteroarenes with aryl diazonium salts in water

UiO-66 is a classic Metal–organic framework (MOF) that constructed by zirconium cations and terephthalate with high chemical and thermal stability. Using pristine UiO-66 nanocrystals as the catalysts, the carbon–carbon bond formation based on denitrogenat

Black phosphorus as a metal-free, visible-light-active heterogeneous photoredox catalyst for the direct C-H arylation of heteroarenes

Black phosphorus (BP) is for the first time employed as a metal-free, heterogeneous photoredox catalyst for the direct C-H arylation of heteroarenes with aryl diazonium salts. The arylated heteroarenes are obtained in moderate to good yields under visible-light illumination, and the protocol is shown to be applicable for the scale-up synthesis.

Carbazole based Electron Donor Acceptor (EDA) catalysis for the synthesis of biaryl and aryl-heteroaryl compounds

A highly regioselective, carbazole based Electron Donor Acceptor (EDA) catalyzed synthesis of biaryl and aryl-heteroaryl compounds is described. Various indole and carbazole derivatives were screened for the Homolytic Aromatic Substitution (HAS) reaction. Tetrahydrocarbazole (THC) was very efficient for the HAS transformation and proceeded via a complex formation between diazonium salt and electron rich tetrahydrocarbazole. The UV-Vis spectroscopy technique has been used to confirm the complex formation. The in situ generated EDA complex even in a catalytic amount is found to be efficient for the Single Electron Transfer (SET) process without any photoactivation. Biaryl compounds, 2-phenylfuran, 2-phenylthiophene, and 2-phenylpyrrole and bioactive compounds such as dantrolene and canagliflozin have been synthesized in moderate to excellent yields.

Phenalenyl Based Aluminum Compound for Catalytic C-H Arylation of Arene and Heteroarenes at Room Temperature

Main group metal based catalysis has been considered to be a cost-effective alternative way to the transition metal based catalysis, due to the high abundance of main group metals in the Earth's crust. Among the main group metals, aluminum is the most abundant (7-8%) in the Earth's crust, making the development of aluminum based catalysts very attractive. So far, aluminum based compounds have been popularly used as Lewis acids in a variety of organic reactions, but chemical transformation demanding a redox based process has never utilized an Al(III) complex as a catalyst. Herein, we tuned the redox noninnocence behavior of a phenalenyl ligand by coupling with Al(III) ion, which subsequently can store the electron upon reduction with K to carry out direct C-H arylation of heteroarenes/mesitylene at ambient temperature. A mechanistic investigation revealed that a three-electron reduced phenalenyl based triradical aluminum(III) complex plays the key role in such catalysis. The electronic structure of the catalytically active triradical species has been probed using EPR spectroscopy, magnetic susceptibility measurements, and electronic structure calculations using a DFT method.

Perylenequinonoid-catalyzed photoredox activation for the direct arylation of (het)arenes with sunlight

Naturally occurring perylenequinonoid pigments (PQPs) have attracted considerable attention owing to their excellent properties of photosensitization. They have been widely investigated as an aspect of photophysics and photobiology. However, their applications in photocatalysis are yet to be explored. We report here that sunlight along with 1 mol% cercosporin, which is one of the perylenequinonoid pigments, catalyzes the direct C-H bond arylation of (het)arenes by a photoredox process with good regioselectivity and broad functional group compatibility. Furthermore, a gram-scale reaction with great conversions of substrates was achieved even by a cercosporin-containing supernatant without organic solvent extraction and purification after liquid fermentation. Thus we set up a bridge between microbial fermentation and organic photocatalysis for chemical reactions in a sustainable, environmentally friendly manner.

Redox reactions of small organic molecules using ball milling and piezoelectric materials

Over the past decade, photoredox catalysis has harnessed light energy to accelerate bond-forming reactions. We postulated that a complementary method for the redox-activation of small organic molecules in response to applied mechanical energy could be dev