1737-16-2

Usage

Uses

Used in Pharmaceutical Industry:
3-(4-Fluorophenyl)-1-propene is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute specific functional groups and structural features that enhance the activity and efficacy of the final drug products.
Used in Agrochemical Industry:
In the agrochemical sector, 3-(4-Fluorophenyl)-1-propene is utilized as a precursor in the development of compounds that possess pesticidal properties, thereby contributing to crop protection and yield enhancement.
Used in Fine Chemicals Production:
3-(4-Fluorophenyl)-1-propene is employed as a building block in the production of fine chemicals, which are high-purity chemicals used in various applications such as fragrances, dyes, and other specialty chemicals.
Used in Polymer and Plastics Industry:
3-(4-FLUOROPHENYL)-1-PROPENE is also used in the synthesis of polymers and plastics, where its fluorinated structure can impart specific properties like resistance to heat and chemicals, which are desirable in various industrial and consumer products.
Given the hazardous nature of 3-(4-Fluorophenyl)-1-propene, it is imperative that its applications are conducted under controlled conditions and with appropriate safety measures to minimize exposure and potential health risks.

InChI:InChI=1/C9H9F/c1-2-3-8-4-6-9(10)7-5-8/h2,4-7H,1,3H2

Upstream product

• 106-95-6 allyl bromide 
• 352-13-6 4-flourophenylmagnesium bromide 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 84648-37-3 C₁₇H₁₄ClFO₄ 
• 591-87-7 Allyl acetate 
• 1765-93-1 4-fluoroboronic acid 
• 107-18-6 allyl alcohol 
• 459-45-0 4-fluorobenzenediazonium tetrafluoroborate 
• 107-05-1 3-chloroprop-1-ene 
• 462-06-6 fluorobenzene 
• 24850-33-7 allyltributylstanane 
• 1746-13-0 allyl phenyl ether 
• 1126-00-7 1-phenylpyrazole 

Downstream Products

• 100921-53-7 4-fluoro-β-methylstyrene 
• 1036384-73-2 5-(4-fluorobenzyl)-3-phenethyl-4,5-dihydro-isoxazole 
• 1073426-77-3 C₁₂H₁₂FNO₄ 
• 1073426-53-5 (E)-methyl 5-(4-fluorophenyl)-2-nitropent-4-enoate 
• 1239921-48-2 9-BBN-6 
• 1250907-71-1 methyl (E)-4-(4-fluorophenyl)-3-butenoate 
• 1357589-74-2 (E)-ethyl 4-((ethoxycarbonothioyl)thio)-5-(4-fluorophenyl)pent-2-enoate 
• 1357591-15-1 (2E,4E)-ethyl 5-(4'-fluorophenyl)penta-2,4-dienoate 
• 1357589-72-0 C₁₇H₂₃FO₄S₃ 
• 1574305-22-8 C₁₆H₁₃FO₂ 
• 504433-86-7 2-[(1E)-2-(4-fluorophenyl)ethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1616285-47-2 (E)-2-(3-(4-fluorophenyl)allyl)cyclohexanone 
• 1627500-42-8 C₂₁H₁₈FNO 

Relevant academic research and scientific papers

Manganese catalyzed dehydrogenative silylation of alkenes: Direct access to allylsilanes

Dehydrogenative silylation of alkenes with silanes to produce allylsilanes is achieved through manganese catalysis with a wide scope of substrate tolerance. This transformation involves silane radicals initiated by manganese complex without additional oxidant additives. It offers a general, convenient and practical protocol with excellent functional group compatibility and gram-scale capacity for the modular synthesis of allylsilanes.

Palladium-Catalyzed Oxidative Allylation of Sulfoxonium Ylides: Regioselective Synthesis of Conjugated Dienones

The first examples of palladium-catalyzed allylic C-H oxidative allylation of sulfoxonium ylides to afford the corresponding conjugated dienones with moderate to good yields have been established. The features of this novel conversion include mild reaction conditions, wide substrate scope, and excellent regioselectivity.

Controllable, Sequential, and Stereoselective C-H Allylic Alkylation of Alkenes

The direct conversion of C-H bonds into new C-C bonds represents a powerful approach to generate complex molecules from simple starting materials. However, a general and controllable method for the sequential conversion of a methyl group into a fully substituted carbon center remains a challenge. We report a new method for the selective and sequential replacement of three C-H bonds at the allylic position of propylene and other simple terminal alkenes with different carbon groups derived from Grignard reagents. A copper catalyst and electron-rich biaryl phosphine ligand facilitate the formation of allylic alkylation products in high branch selectivity. We also present conditions for the generation of enantioenriched allylic alkylation products in the presence of catalytic copper and a chiral phosphine ligand. With this approach, diverse and complex products with substituted carbon centers can be generated from simple and abundant feedstock chemicals.

Palladium-catalyzed allylic C-H oxidation under simple operation and mild conditions

We discovered an effective and simple system (Pd/BQ/air/r.t.) for making allylic alcohols through Pd-catalyzed allylic C-H bond functionalization. This approach exhibits advantages due to its simple operation, mild conditions, and environmentally benign features. By modifying reaction conditions, it can be suitable for preparing unsaturated aldehydes, allylic esters, ethers, and amines.

Palladium-catalyzed oxidative allylation of bis[(pinacolato)boryl]methane: Synthesis of homoallylic boronic esters

A palladium-catalyzed oxidative allylation of bis[(pinacolato)boryl]methane to afford the corresponding homoallylic organoboronic esters with moderate to excellent yields is reported. This novel transformation provides an efficient strategy for the construction of homoallylic organoboronic esters in one step with a broad substrate scope. It is proposed that the palladium-catalyzed oxidative allylic C-H bond activation process may be involved in the catalytic cycle.

Anti-Markovnikov rearrangement in sulfur mediated allylic C-H amination of olefins

Cationic rearrangement reactions usually follow Markovnikov's rule to give more substituted carbocations as stable intermediates. During our study on sulfur mediated allylic C-H amination of olefins, very rare cases of anti-Markovnikov rearrangement from secondary carbocations toward primary carbocations or primary triflates were observed.

Trifluoromethylchlorosulfonylation of alkenes: Evidence for an inner-sphere mechanism by a copper phenanthroline photoredox catalyst

Abstract A visible-light-mediated procedure for the unprecedented trifluoromethylchlorosulfonylation of unactivated alkenes is presented. It uses [Cu(dap)2]Cl as catalyst, and contrasts with [Ru(bpy)3]Cl2, [Ir(ppy)2(dtbbpy)]PF6, or eosin Y that exclusively give rise to trifluoromethylchlorination of the same alkenes. It is assumed that [Cu(dap)2]Cl plays a dual role, that is, acting both as an electron transfer reagent as well as coordinating the reactants in the bond forming processes. Double role: The trifluoromethylchlorosulfonylation of unactivated alkenes was developed using [Cu(dap)2]Cl as catalyst (dap=2,9-bis(para-anisyl)-1,10-phenanthroline). [Cu(dap)2]Cl plays a dual role; acting as an electron transfer reagent as well as coordinating the reactants in the bond forming processes.

Palladium-catalyzed aerobic oxidative double allylic C-H oxygenation of alkenes: A novel and straightforward route to α,β-unsaturated esters

A mild tandem oxidative functionalization of allyl aromatic hydrocarbons was accomplished using the catalytic system of Pd(OAc)2/DMA under 1 atm O2. The green twofold C-O bond formation involving double allylic C-H oxygenation unlocks opportunities for markedly different synthetic strategies. Moreover, the reaction affords aryl α,β-unsaturated esters directly from readily available terminal olefins in moderate to good yields with excellent chemo- and stereoselectivities.

Direct conversion of allyl arenes to aryl ethylketones via a TBHP-mediated palladium-catalyzed tandem isomerization-Wacker oxidation of terminal alkenes

A TBHP-mediated palladium-catalyzed tandem isomerization-Wacker oxidation of terminal alkenes was developed. This methodology provides a new efficient and simple route for conversion of a range of allyl arenes directly into aryl ethylketones in good yields with high chemoselectivity.

Ortho-allylation of 1-arylpyrazoles with allyl phenyl ether via iron-catalyzed C-H bond activation under mild conditions

An iron salt and a bipyridine-type ligand catalyze the ortho-allylation of 1-arylpyrazoles and congeners with allyl phenyl ether under mild conditions (0 °C). The ligand, an organozinc base, and the nature of the allylating reagent are crucial for the success of this reaction. Under these conditions, a competitive phenylation reaction is largely retarded, and cross-coupling of the organozinc with the allyl electrophile is minimized. The reaction may proceed via iron-catalyzed ortho C-H activation to form a metallic intermediate, which then reacts with the allyl ether in a γ selective fashion.