4333-75-9

Usage

Classification

Derivative of styrene, belongs to the family of phenyl ethenes

Physical state

Colorless liquid at room temperature

Odor

Sweet, floral

Usage

Commonly used in the manufacture of perfumes and fragrances, production of polymers, and as a flavoring agent in the food industry

Safety precautions

May cause skin and eye irritation upon contact, handle with caution

InChI:InChI=1/C15H14O/c1-12(13-6-4-3-5-7-13)14-8-10-15(16-2)11-9-14/h3-11H,1H2,2H3

Upstream product

• 71-23-8 propan-1-ol 
• 611-94-9 4-Methoxybenzophenone 
• 917-64-6 methyl magnesium iodide 
• 60-29-7 diethyl ether 
• 94001-65-7 1-(4-methoxyphenyl)-1-phenylethan-1-ol 
• 100-42-5 styrene 
• 1600-27-7 mercury(II) diacetate 
• 100-66-3 methoxybenzene 
• 17256-00-7 1-(4-hydroxyphenyl)-1-phenylethylene 
• 77-78-1 dimethyl sulfate 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 71897-86-4 (E/Z)-1,3-(4-methoxyphenyl)-1,3-diphenylbut-2-ene 
• 71-43-2 benzene 
• 76-03-9 trichloroacetic acid 

Downstream Products

• 17684-11-6 3-(4-anisyl)cinnamic acid 
• 24845-40-7 2-(4-methoxyphenyl)acetophenone 
• 16343-36-5 2-(4-methoxy-phenyl)-2-phenylacetaldehyde 
• 2605-18-7 1-methoxy-4-(1-phenylethyl)benzene 
• 71897-86-4 (E/Z)-1,3-(4-methoxyphenyl)-1,3-diphenylbut-2-ene 
• 211930-12-0 2-hydroxy-2-(4-methoxyphenyl)-2-phenylacetaldehyde 
• 58617-69-9 1-(2,2-difluoro-2-phenylethyl)-4-methoxybenzene 
• 54766-43-7 2-p-Methoxy-phenyl-2-phenyl-vinyliodid 
• 135754-59-5 methyl 2-(4-methoxyphenyl)-2-phenylethyl ether 
• 135754-65-3 C₃₁H₃₂O₃ 
• 5556-73-0 2-bromo-1-(4-methoxyphenyl)-1-phenylethene 

Relevant academic research and scientific papers

The Concept of Photozymes: Short Peptides with Photoredox Catalytic Activity for Nucleophilic Additions to α-Phenyl Styrenes

Conventional photoredox catalytic additions of alcohols to olefins require additives, like thiophenol, to promote back electron transfer. The concept of “photozymes” assumes that forward and backward electron transfer steps in a photoredox catalytic cycle

TMSOTf-mediated synthesis of skipped dienes through the addition of olefins to imines and semicyclicN,O-acetals

A novel approach to skipped dienes has been developed through the TMSOTf-mediated one-pot addition-substitution of olefins2a,2fand2gwith imines1a-1g, and a series of aryl substituted skipped dienes3aa-3gfwere accordingly obtained in 62%-94% yields. Moreov

Photoredox-Catalyzed α-Aminomethyl Carboxylation of Styrenes with Sodium Glycinates: Synthesis of γ-Amino Acids and γ-Lactams

A visible-light photoredox-catalyzed reductive α-aminomethyl carboxylation of styrenes with sodium glycinates and CO2 has been developed to synthesize a series of α,α-disubstituted γ-amino acids and γ-lactams with high efficiency and regioselectivity. Notably, CO2 released from the decarboxylation step can be reused for the subsequent carboxylation. Distinct from the previous reactions with the same type of substrates leading to simple decarboxylation and olefin hydroalkylation, this process involves additional CO2 sequestration, thus leading to olefin α-aminomethyl carboxylation. These findings not only provide new access to α,α-disubstituted γ-amino acids and γ-lactams but also serve as a proof of concept for CO2 reutilization in decarboxylation reactions.

Nickel-Catalyzed Regiodivergent Reductive Hydroarylation of Styrenes

We report a ligand-controlled nickel-catalyzed reductive hydroarylation of styrenes with predictable and controllable regioselectivity. With a diamine ligand, the reaction produces selective linear hydroarylation products. Alternatively, with a chiral PyrOx ligand, branch-selective enantioenriched 1,1-diarylalkane products are obtained. Preliminary mechanistic results are consistent with a reductive Heck process.

Enantioselective Radical-Polar Crossover Reactions of Indanonecarboxamides with Alkenes

Highly efficient asymmetric intermolecular radical-polar crossover reactions were realized by combining a chiral N,N′-dioxide/NiII complex catalyst with Ag2O under mild reaction conditions. Various terminal alkenes and indanonecarboxamides/esters underwent radical addition/cyclization reactions to afford spiro-iminolactones and spirolactones with good to excellent yields (up to 99 %) and enantioselectivities (up to 97 % ee). Furthermore, a range of different radical-mediated oxidation/elimination or epoxide ring-opening products were obtained under mild reaction conditions. The Lewis acid catalysts exhibited excellent performance and precluded the strong background reaction.

Deaminative carbonylative coupling of alkylamines with styrenes under transition-metal-free conditions

A transition-metal-free deaminative carbonylation of alkylamines with styrenes has been developed. The reaction shows good functional group compatibility and various α,β-unsaturated ketones were obtained in moderate to good yields. The alkyl radical generated from Katritzky salts via base-promoted C-N bond cleavage is one of the key intermediates in this reaction. This journal is

New poly-imidazolium-triazole particles by CuAAC cross-linking of calix[4]arene bis-azide/alkyne amphiphiles - a prospective support for Pd in the Mizoroki-Heck reaction

A new imidazolium amphiphilic calix[4]arene with terminal acetylene fragments in the polar region was synthesized according to a two step scheme including regioselective chloromethylation of distal di-O-butyl calix[4]arene and subsequent interaction with 1-(hex-5-yn-1-yl)-1H-imidazole. The aggregation properties (CAC, the size and zeta potential of aggregates) of alkynyl calix[4]arene as well as of previously synthesized azidopropyl calix[4]arene and their 1?:?1 mixture were disclosed. Macrocycles with azide and alkyne fragments in the polar region were covalently cross-linked under CuAAC conditions in water. Successful cross-linking of molecules has been proven by IR spectroscopy and MALDI-TOF spectrometry. The obtained polymeric particles were studied both in solution and the solid state and the presence of submicron (～200 nm) and micron (～1-5 μm) particles with the prevalence of the latter was found. The average molecular weight of the polymer according to the static light scattering data was found to be 639 ± 44 kDa. The obtained polymeric imidazolium-triazole particles were tested as a support for Pd(OAc)2in the Mizoroki-Heck reaction carried out in both organic and water media. In both solvents (especially in water) the addition of imidazolium-triazole particles to Pd(OAc)2increased the conversion of 4-iodanisole. It was found that the ratio between the products (1,1 and 1,2-substituted ethylenes) changes drastically on going from DMF to water from 1?:?5 to 1?:?40 when using supported Pd(OAc)2

Regiodivergent DH or HD Addition to Alkenes: Deuterohydrogenation versus Hydrodeuterogenation

The regioselective and regiodivergent addition of H-D to a variety of 1,1-diarylalkenes was realized utilizing selectively deuterated dihydroaromatic compounds, which were generated by cobalt catalysis. The reaction was initiated by catalytic amounts of B

Halogenation of 1,1-diarylethylenes by N-halosuccinimides

An efficient method for the preparation of 2,2-diarylvinyl halides from the corresponding 1,1-diarylethylenes has been developed. N-Halosuccinimides (N-bromosuccinimide or N-chlorosuccinimide) were used as the halogenation reagents. The practicability of this method is highlighted by its simple operation, broad substrate scope and capability for large-scale reaction.

Photocatalytic, Phosphoranyl Radical-Mediated N-O Cleavage of Strained Cycloketone Oximes

A photoinduced, phosphoranyl radical-mediated protocol for the direct N-O cleavage of strained cycloketone oximes via a polar/SET crossover process was developed for the first time. This visible-light-driven direct N-O activation mode for oxime offers beneficial features such as streamlined synthetic process and versatile photochemical reactivities. Consequently, the alkenes and α-trifluoromethyl alkenes with varied electronic and structural features acted as competent radical receptors in this protocol, enabling facile accesses to a range of elongated cyano and/or gem-difluoroalkene-bearing compounds.