210536-47-3

Usage

Uses

Used in Chemical Synthesis Industry:
Benzenamine, 2-ethenyl-4-methoxy(9CI) is used as an intermediate in the synthesis of various organic compounds for the chemical industry. Its unique structure allows it to be a versatile building block in the creation of a wide range of products.
Used in Dye and Pigment Production:
Benzenamine, 2-ethenyl-4-methoxy(9CI) is used as a key component in the production of dyes and pigments. Its chemical properties enable it to impart color and stability to these products, making it an essential ingredient in this application.
Used in Pharmaceutical Industry:
Benzenamine, 2-ethenyl-4-methoxy(9CI) is used as a precursor in the synthesis of pharmaceuticals. Its presence in the manufacturing process contributes to the development of various medications, highlighting its importance in the healthcare sector.

Upstream product

• 104-94-9 4-methoxy-aniline 
• 74-86-2 acetylene 
• 639006-06-7 2-ethenyl-4-methoxyphenyl carbamic acid ethyl ester 
• 32338-02-6 2-bromo-4-methoxyaniline 
• 206432-09-9 2-bromo-4-methoxyphenyl carbamic acid ethyl ester 
• 126759-31-7 2-vinyl-4-methoxynitrobenzene 
• 1882-69-5 5-methoxy-2-nitro-benzoic acid 
• 879-55-0 (5-methoxy-2'-nitrophenyl)methanol 
• 20357-24-8 5-methoxy-2-nitro-benzaldehyde 

Downstream Products

• 1420809-03-5 C₂₀H₂₉NO₂ 
• 139717-71-8 5-methoxy-N-(4-toluenesulfonyl)-1H-indole 
• 522613-62-3 (4-methoxy-2-vinylphenyl)carbamic acid tert-butyl ester 
• 116707-99-4 1,3-dimethyl-5-methoxyindolin-2-one 

Relevant academic research and scientific papers

Iron-Catalyzed Reductive Cyclization by Hydromagnesiation: A Modular Strategy Towards N-Heterocycles

A reductive cyclization to prepare a variety of N-heterocycles, through the use of ortho-vinylanilides, is reported. The reaction is catalyzed by an inexpensive and bench-stable iron complex and generally occurs at ambient temperature. The transformation likely proceeds through hydromagnesiation of the vinyl group, and trapping of the in situ generated benzylic anion by an intramolecular electrophile to form the heterocycle. This iron-catalyzed strategy was shown to be broadly applicable and was utilized in the synthesis of substituted indoles, oxindoles and tetrahydrobenzoazepinoindolone derivatives. Mechanistic studies indicated that the reversibility of the hydride transfer step depends on the reactivity of the tethered electrophile. The synthetic utility of our approach was further demonstrated by the formal synthesis of a reported bioactive compound and a family of natural products.

Electrochemical-mediated fixation of CO2: three-component synthesis of carbamate compounds from CO2, amines andN-alkenylsulfonamides

An electrocatalyzed three-component cascade reaction of CO2, amines, andN-alkenylsulfonamides is developed, providing an environmentally friendly and efficient method of synthesizing a series of new carbamate compounds. This reaction meets the needs of green chemistry and promotes the participation of carbon dioxide in the three-component reaction by electro-oxidation. Pharmacological activity studies further prove that carbamate compounds have better activity than diamination by-products.

Hydroxyl Assisted Rhodium Catalyst Supported on Goethite Nanoflower for Chemoselective Catalytic Transfer Hydrogenation of Fully Converted Nitrostyrenes

Control of chemoselectivity is a special challenge for the reduction of nitroarenes bearing one or more unsaturated groups. Here, we report a flower-like Rh/α-FeOOH catalyst for the chemoselective hydrogenation of nitrostyrene to vinylaniline over full conversion, which benefits the new functionalized aminostyrene because the multisubstituted aminostyrenes are usually commercially unavailable. This catalyst does not only show desirable selectivity for the vinylanilines, but also exhibits the inertness to various other reducible groups over wide reaction duration. The catalytic selectivity for the reduction of the nitro group towards vinyl group was investigated by the control experiments and FT-IR analysis. We have found that the abundant hydroxyl groups in the α-FeOOH may contribute to the improvement of catalytic activity and selectivity. Furthermore, the catalyst exhibits excellent stability and keeps its catalytic performance even after 6 cycles. (Figure presented.).

Pd-tBuONO Cocatalyzed Aerobic Indole Synthesis

A Pd-tBuONO co-catalyzed scalable and practical synthesis of indoles with molecular oxygen as terminal oxidant is developed. Either terminal or internal 2-vinylanilines could be smoothly converted to desired indoles under one general condition. This method has been evaluated in the large scale synthesis of indomethacin and a potential anti-breast cancer drug candidate 1. (Figure presented.).

Direct Synthesis of Structurally Divergent Indole Alkaloids from Simple Chemicals

A direct and structurally divergent synthesis of indole alkaloids from very simple 2-vinylanilines, alkynes and TBN via a novel substrate fragmentation/cycloaddition strategy has been developed, which provides an efficient noble-metal-free approach to access a library of highly valuable indole derivatives of tryptamines and tryptamine-related oximes, lactams, and lactones, as well as β-carbolines, spiroindolines, and hexa-hydropyrrolo[2,3-b]indoles.

Direct Tryptophols Synthesis from 2-Vinylanilines and Alkynes via C - C Triple Bond Cleavage and Dioxygen Activation

An unexpected metal-free C - C triple bond cleavage, dioxygen activation, and reassembly into tryptophol derivatives has been developed. This chemistry provides a novel, simple, and efficient approach to highly valuable tryptophol derivatives from simple substrates under mild conditions. The mechanistic studies may promote the discovery of new methodologies through C-C bond cleavage and dioxygen activation.

Highly Diastereo- and Enantioselective CuH-Catalyzed Synthesis of 2,3-Disubstituted Indolines

A diastereo- and enantioselective CuHcatalyzed method for the preparation of highly functionalized indolines is reported. The mild reaction conditions and high degree of functional group compatibility as demonstrated with substrates bearing heterocycles,

Intramolecular cyclization reactions of unsaturated amino Fischer chromium carbenes forming indoles and quinolines

A thermally induced intramolecular annulation reaction of N-(2-alkenylphenyl)amino substituted Fischer chromium carbenes has been extensively examined. The carbene complexes were prepared in moderate to good yields by reaction of 2-aminostyrenes with intermediately formed acyloxy substituted carbenes. Upon heating, the thermally labile carbenes decomposed producing indoles and quinolines as the major products. The product distribution was found to be highly dependent on the substitution pattern and electronic properties of the starting material, and on the solvent used.

Ortho-Vinylation reaction of anilines

N-Alkylanilines and anilines are vinylated at the ortho-position with ethyne in the presence of SnCl4-Bu3N.