39082-40-1

Usage

Uses

Used in Pharmaceutical Industry:
1-(4-METHOXYPHENYL)-2-(4-NITROPHENYL)-ACETYLENE is used as an intermediate in the synthesis of various organic compounds and pharmaceuticals. Its unique structure allows it to be a key component in the development of new drugs and medications, contributing to the advancement of pharmaceutical research and innovation.
Used in Organic Synthesis:
In the field of organic chemistry, 1-(4-METHOXYPHENYL)-2-(4-NITROPHENYL)-ACETYLENE serves as a valuable intermediate for the synthesis of a wide range of organic compounds. Its versatility in chemical reactions makes it an essential tool for creating complex molecular structures with potential applications in various industries, including materials science, agrochemicals, and specialty chemicals.

Upstream product

• 636-98-6 p-nitrobenzene iodide 
• 768-60-5 4-methoxyphenylacetylen 
• 4648-33-3 (E)-1-methoxy-4-(4-nitrostyryl)benzene 
• 937-31-5 (4-Nitrophenyl)acetylene 
• 696-62-8 para-iodoanisole 
• 15794-99-7 (α,α'-dibromo-4'-nitro-bibenzyl-4-yl)-methyl ether 
• 123-11-5 4-methoxy-benzaldehyde 
• 75867-38-8 4-nitro-1-(trimethylsilylethynyl)benzene 
• 51738-10-4 2,2-dibromo-1-(4-nitrophenyl)ethene 
• 33397-21-6 tris(4-methoxyphenyl)bismuth 
• 1237789-51-3 C₁₄H₁₄BNO₅ 
• 586-78-7 para-nitrophenyl bromide 
• 69116-22-9 1-(iodoethynyl)-4-nitrobenzene 
• 5720-07-0 4-methoxyphenylboronic acid 

Downstream Products

• 874988-48-4 1-benzyl-4-(4-methoxy-phenyl)-5-(4-nitro-phenyl)-1H-[1,2,3]triazole 
• 1256651-25-8 C₄₁H₃₃NO₈ 
• 1259284-12-2 C₂₄H₂₀N₂O₄ 
• 1259284-13-3 C₂₄H₂₀N₂O₄ 
• 1352608-62-8 [(η4-C4(C6H4-4-NO2)2(C6H4-4-OMe)2)Co(η5-C5H5)] 
• 1352608-44-6 [(η4-C4(C6H4-4-NO2)2(C6H4-4-OMe)2)Co(η5-C5H5)] 
• 1404432-72-9 1-(iodomethyl)-2-(4-nitrophenyl)-1-methyl-3-(4-methoxyphenyl)-1H-indene 
• 1404432-73-0 1-(iodomethyl)-2-(4-methoxyphenyl)-1-methyl-3-(4-nitrophenyl)-1H-indene 
• 1434153-00-0 2-(4-methoxyphenyl)-1-(4-nitrophenyl)-4-phenoxy-3Hpyrrolo[3,2,1-de]acridin-3-one 
• 1434153-01-1 2-(4-methoxyphenyl)-1-(4-nitrophenyl)-4-phenoxy-3Hpyrrolo[3,2,1-de]acridin-3-one 
• 1434153-06-6 4-benzyl-1-(4-nitrophenyl)-2-(4-methoxyphenyl)-3Hpyrrolo[3,2,1-de]acridin-3-one 
• 1434153-07-7 4-benzyl-1-(4-methoxyphenyl)-2-(4-nitrophenyl)-3H-pyrrolo[3,2,1-de]acridin-3-one 
• 1434153-10-2 8-methoxy-2-(4-methoxyphenyl)-1-(4-nitrophenyl)-4-phenoxy-3H-pyrrolo[3,2,1-de]acridin-3-one 
• 1434153-11-3 C₃₅H₂₄N₂O₆ 

Relevant academic research and scientific papers

A New Organic Material Exhibiting Highly Efficient Phase-matched Second Harmonic Generation: 4-Methoxy-4'-nitrotolan

The high second harmonic efficiency with phase-matchable characteristics of a new nonlinear optical material, 4-methoxy-4'-nitrotolan, is reported.

Co3O4 nanoparticles embedded in triple-shelled graphitic carbon nitride (Co3O4/TSCN): a new sustainable and high-performance hierarchical catalyst for the Pd/Cu-free Sonogashira–Hagihara cross-coupling reaction

Inspired by the synthesis of triple-shelled periodic mesoporous organosilica hollow spheres, a straightforward and controllable approach for the preparation of Co3O4 NPs embedded in triple-shelled graphitic carbon nitride has been es

Atom-Economical Thiocyanation-Amination of Alkynes with N-Thiocyanato-Dibenzenesulfonimide

A highly regioselective protocol for intermolecular thiocyanation-amination of alkynes by N-thiocyano-dibenzenesulfonimide (NTSI) as the SCN and nitrogen sources has been developed. A C-S bond and C-N bond are simultaneously constructed in only one step. The reaction under simple mild conditions features a broad substrate scope, atom economy, high yields (up to 94%), and excellent functional group tolerance.

Metal scavenging and catalysis by periodic mesoporous organosilicas with 2,2′-bipyridine metal chelating ligands

A periodic mesoporous organosilica containing 2,2′-bipyridine (BPy-PMO) was assessed as a metal scavenger and heterogeneous catalyst. The functionalized PMO was synthesized based on a modified version of a previously reported procedure and showed a large

Magnetic chitosan-functionalized cobalt-NHC: Synthesis, characterization and catalytic activity toward Suzuki and Sonogashira cross-coupling reactions of aryl chlorides

Aryl chlorides are one of the most stable and available electrophiles, however, their coupling with nucleophiles remains a challenge in organic synthesis. Herein, we prepared a Cobalt-NHC (N-Heterocyclic carbene) complex anchored on magnetic chitosan nanoparticles and assayed its catalytic activity for the reactions of substituted phenylboronic acid and also phenlacetylene with derivatives of aryl chlorides. These reactions are of great importance since they are employed for the synthesis of unsymmetrical diarylethynes and biphenyls, which belong to a prime class of building blocks. The synthesized nanocatalyst was found to be highly efficient in Suzuki and Sonogashira coupling in terms of their activity and recyclability in polyethylene glycol (PEG) as a green reaction media under conditions of temperatures (70 and 100 °C) and Co loading (3 and 6 mol%). To the best of our knowledge, this is the first attempt of using cobalt-NHC complex for catalyzing the abovementioned reactions. Moreover, replacing the earth-abundant Cobalt-based catalyst as an alternative to high cost palladium make this approach promising from sustainable chemistry view.

Phenazine-Based Donor Acceptor Systems as Organic Photocatalysts for "metal-free" C-N/C-C Cross-Coupling

With an aim to achieve a balance between ground-state and excited-state reduction potential of donor acceptor systems for efficient C-N/C-C cross-coupling, a series of donor acceptor systems DA1-DA4 have been synthesized by varying the donor strength and connecting positions. With an increase in donor strength, systematic elevation in the ground-state reduction potential and decrease in the HOMO-LUMO gap was observed. Interestingly, all the derivatives DA1-DA4 could catalyze the C-N bond formation reaction between activated aryl halides and amines at low catalytic loading under metal-free conditions without the need of any external base upon irradiation with white LED. A balance was realized in the case of derivative DA2, which exhibits high efficiency in C-N couplings. Different control experiments support the validity of the energy as well as electron transfer pathways in the visible light-mediated C-N bond formation. This study further reveals the potential of derivative DA1 in "metal-free"Sonogashira coupling involving activated aryl halides which is attributed to its high excited-state reduction potential.

Rate Enhancement in CAN-Promoted Pd(PPh3)2Cl2-Catalyzed Oxidative Cyclization: Synthesis of 2-Ketofuran-4-carboxylate Esters

Stoichiometric ceric ammonium nitrate (CAN) and a catalytic amount of Pd(PPh3)2Cl2 (5 mol %) can rapidly produce multisubstituted 2-ketofuran-4-carboxylate esters from 2-propargylic 1,3-ketoesters via oxidative O-cyclization reaction. Pd(PPh3)2Cl2 was found to be the crucial catalyst as its inclusion greatly enhanced the rate of the reaction and cleanly afforded the products within minutes. Over 30 substrates were successfully converted to the desired compounds in mostly moderate to good yields.

Sequentially Pd/Cu-Catalyzed Alkynylation-Oxidation Synthesis of 1,2-Diketones and Consecutive One-Pot Generation of Quinoxalines

We report a simple and efficient one-pot synthesis of 1,2-diketones by concatenation of two Pd/Cu-catalyzed processes: Pd0/CuI-catalyzed Sonogashira coupling of terminal alkynes with aryl (pseudo)halides furnishes internal alkynes, which are directly transformed by PdII/CuII-catalyzed Wacker-type oxidation with DMSO and oxygen as dual oxidants to furnish 1,2-diketones. With this efficient, catalyst economical process, various aryl iodides and triflates are efficiently transformed in high yields into symmetrically and unsymmetrically substituted 1,2-diketones with various functional groups. This process can be readily extended to a consecutive one-pot synthesis of quinoxalines in a diversity-oriented fashion.

Synthesis of Diarylacetylenes Bearing Electron-Withdrawing Groups via the Smiles Rearrangement

Nitrobenzyl benzothiazol-2-yl sulfones and nitrobenzyl 1-phenyl-1 H -tetrazol-5-yl sulfones react with chlorides of aromatic acids to form β-acyl derivatives. These products undergo the Smiles rearrangement resulting in the formation of the corresponding nitrophenyl arylacetylenes in 50-60% overall yields (approx. 75% per step). Sulfones bearing CF 3 or CN groups instead of a NO 2 substituent form mixtures of the acetylenes in moderate yields and benzyl aryl ketones in yields above 40%.

Pd-Catalyzed decarboxylative alkynylation of alkynyl carboxylic acids with arylsulfonyl hydrazides via a desulfinative process

In the presence of a Pd(ii)/P-ligand catalytic system, decarboxylative alkynylation of alkynyl carboxylic acids and arylsulfonyl hydrazides by desulfinative coupling could provide aryl alkynes in satisfactory yields by either judiciously selecting palladium catalysts or modulating phosphine ligands under mild conditions. The reported coupling reactions are very practical as they do not require the protection of inert gas or oxygen and are tolerant to many functional groups.