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Usage

Uses

Used in Organic Chemistry:
4-Fluoro-2-(phenylethynyl)benzaldehyde serves as a key building block in the synthesis of various compounds. Its unique structure allows for the creation of a wide range of pharmaceuticals, agrochemicals, and materials, contributing to the advancement of these fields.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-fluoro-2-(phenylethynyl)benzaldehyde is utilized as a precursor for the development of new drugs. Its specific chemical properties enable the design and synthesis of molecules with potential therapeutic effects, addressing unmet medical needs.
Used in Agrochemical Industry:
4-Fluoro-2-(phenylethynyl)benzaldehyde also finds application in the agrochemical sector, where it is employed in the synthesis of novel agrochemicals. Its unique structure aids in the development of compounds with improved pesticidal or herbicidal properties, enhancing crop protection and yield.
Used in Materials Science:
In the field of materials science, 4-fluoro-2-(phenylethynyl)benzaldehyde is used for the development of new materials with specific properties. Its incorporation into material compositions can lead to the creation of materials with tailored characteristics for various applications, such as in electronics or advanced manufacturing.
Used in Research and Development:
4-Fluoro-2-(phenylethynyl)benzaldehyde is extensively used in research and development due to its unique chemical properties and potential applications. It serves as a valuable tool for scientists and researchers to explore new chemical reactions, synthesis pathways, and the development of innovative products across various industries.

Upstream product

• 59142-68-6 2-bromo-4-fluorobenzaldehyde 
• 536-74-3 phenylacetylene 
• 1044572-84-0 4-((4-fluoro-2-(phenylethynyl)phenyl)sulfinyl)-N,N-dimethylaniline 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 1198019-11-2 2-(6-fluoro-2-(4-methoxyphenyl)-3-phenyl-1,2-dihydroisoquinolin-1-yl)pent-1-en-3-one 
• 1198019-04-3 3-(6-fluoro-2-(4-methoxyphenyl)-3-phenyl-1,2-dihydroisoquinolin-1-yl)but-3-en-2-one 
• 1239485-85-8 3-fluoro-6-phenyl-10,11-dihydroindazolo[3,2-a]isoquinolin-12(9H)-one 
• 1207290-03-6 2-benzyl-6-fluoro-1-(2-methyl-1H-indol-3-yl)-3-phenyl-1,2-dihydroisoquinoline 
• 1227172-61-3 C₁₆H₉Br₂F 
• 1242337-04-7 C₂₇H₁₈FN₃ 
• 1242149-47-8 C₂₆H₂₄F₄NO₃P 
• 1242149-44-5 C₂₇H₂₇FNO₄P 
• 1242149-39-8 C₂₆H₂₇FNO₃P 
• 1242149-51-4 C₂₅H₂₄ClFNO₃P 
• 1242149-42-3 C₂₆H₂₇FNO₄P 
• 1242149-41-2 C₂₇H₂₉FNO₃P 
• 1242149-49-0 C₂₅H₂₄FN₂O₅P 
• 1242149-43-4 C₂₅H₂₅FNO₄P 

Relevant academic research and scientific papers

Catalytic Asymmetric Tandem Reaction of o-Alkynylbenzaldehydes, Amines, and Diazo Compounds

An efficient asymmetric tandem reaction of o-alkynylbenzaldehydes, amines, and diazo compounds catalyzed by chiral silver imidodiphosphate has been established. Chiral 1,2-dihydroisoquinoline analogues have a tertiary stereocenter at the C1 position, and substituents at the C3 position are available with up to 97% yields and 98% ee. These products can be elaborated into the corresponding β-aminophosphonates or PARP1-inhibitor analogues.

Tunable Synthesis of Indeno[1,2- c]furans and 3-Benzoylindenones via FeCl3-Catalyzed Carbene/Alkyne Metathesis Reaction of o-Alkynylbenzoyl Diazoacetates

An efficient synthesis of indeno[1,2-c]furan and 3-benzoylindenone derivatives through a FeCl3-catalyzed carbene/alkyne metathesis reaction of o-alkynylbenzoyl diazoacetates is presented. Mechanistically, the key intermediate, vinyl iron carbene, is formed by 5-exo-dig carbocyclization and terminated with a formal [3 + 2] cycloaddition or carbonylation. To the best of our knowledge, this is the first example in which FeCl3 is used as a catalyst for a carbene/alkyne metathesis reaction. Finally, derivatization reactions were carried out to showcase the value of the products.

Palladium-catalyzed cascade decarboxylative amination/6- endo-dig benzannulation of o-alkynylarylketones with n-hydroxyamides to access diverse 1-naphthylamine derivatives

An efficient and practical one-pot strategy to produce highly substituted 1-naphthylamines via sequential palladium-catalyzed decarboxylative amination/intramolecular 6-endo-dig benzannulation reactions has been described. In this reaction, a broad range of electron-rich, electron-neutral, and electron-deficient o-alkynylarylketones react well with N-hydroxyl aryl/alkylamides to give a diversity of 1-naphthylamines in good to excellent yields under mild reaction conditions. The gram-scale synthesis, with benefits such as undiminished product yield and easy transformation, illustrated the practicality of this method.

Catalytic asymmetric three-component reaction of 2-alkynylbenzaldehydes, amines, and dimethylphosphonate

An efficient enantioselective synthesis of cyclic α-aminophosphonates via multicomponent reactions of 2-alkynylbenzaldehydes, amines, and dimethylphosphonate has been developed with the use of a chiral silver spirocyclic phosphate as the catalyst. This protocol provides straightforward access to a series of chiral C1-phosphonylated 1,2-dihydroisoquinoline derivatives with high yields (up to 99%) and high enantioselectivities (up to 94% ee) for a broad substrate scope. The products could be further transformed into densely functionalized compounds and corresponding α-aminophosphonic acids.

Carbonyl-Directed Addition of N-Alkylhydroxylamines to Unactivated Alkynes: Regio- and Stereoselective Synthesis of Ketonitrones

A variety of ketonitrones were synthesized in moderate to excellent yields with high chemo-, regio-, and stereoselectivity by using carbonyl-directed addition of N-alkylhydroxylamines to unactivated alkynes under mild conditions. The product diverisity could be controlled by the use of different bases, and EtN(n-Pr)2 could promote the formation of ketonitrones while using EtONa as base led to indanone-derived nitrones. Control experiments indicated that the carbonyl group of the substrate acted as an H-bond acceptor except for an electron-withdrawing group, and conjugated enone skeleton accounted for the high selectivity.

Synthesis of Functionalized Cyclobutane-Fused Naphthalene Derivatives via Cascade Reactions of Allenynes with tert-Butyl Nitrite

A novel synthesis of cyclobutanol-fused 2-nitronaphthalen-1-ols and nitrocyclobutane-fused naphthalene-1,2-diones through cascade reactions of benzene-linked allenynes with tert-butyl nitrite is presented. The formation of the title compounds involves a tandem process including allenyne [2+2] cycloaddition, radical addition onto the in situ formed cyclobutenyl moiety followed by radical coupling/oxidation. Interestingly, different kinds of functionalized naphthalene derivatives could be obtained selectively from the same substrates, and the selectivity was easily controlled by finely tuning the reaction conditions. (Figure presented.).

Completely Stereoselective Synthesis of Sulfonated 1,3-Dihydroisobenzofurans via Radical Multicomponent Reactions

Two types of new oxidant-free radical multicomponent reactions of β-alkynyl ketones, aryldiazonium salts, and DABCO·(SO2)2 (DABSO) were established, leading to the tunable generation of two class of sulfonated 1,3-dihydroisobenzofurans with moderate to good yields and complete stereoselectivity under the mild conditions. The radical-induced scission/recombination of the C(sp3)-C(sp3) bond enabled direct 1,8-halosulfonylation of β-alkynyl ketones, giving 1,3-dimethylene-substituted (1Z,3Z)-1,3-dihydroisobenzofurans with substituent diversity by p-nitrobenzyl bromide (PNBB) or p-nitrobenzyl chloride (PNBC) as the halo source. Fine-tuning substituents to strong electron-withdrawing ones, such as nitro, cyano, and trifluoromethyl, linked to aryldiazonium tetrafluoroborates allowed a different annulation/1,5-azosulfonylation process to access sulfonated (Z)-1,3-dihydroisobenzofurans with one quaternary carbon-amino functionality.

Radical-Triggered Tandem Cyclization of 1,6-Enynes with H2O: A Way to Access Strained 1 H-Cyclopropa[ b]naph thalene-2,7-diones

A radical-triggered tandem cyclization of 1,6-enynes has been developed herein. Strained 1H-cyclopropa[b]naphthalene-2,7-diones are successfully obtained in moderate to good yields with excellent stereoselectivity. Mechanistic studies reveal a key role of water in generating a hydroxyl radical that initiates a sequential Michael addition/ring closure pathway. Importantly, the formed hydroxyl is proposed to be a good leaving group during the cyclopropane ring formation.

Cobalt-catalyzed regioselective syntheses of indeno[2,1-: C] pyridines from nitriles and diynes bearing propargyl fragments

A highly efficient CoI2/o-phenanthroline catalyzed cycloaddition reaction of diynes bearing TBS protected propargylic alcohol fragments with nitriles has been developed. This methodology offers regioselective access, with good functional group tolerance, to various indeno[2,1-c]pyridine derivatives in moderate to excellent yields. It was found that o-phenanthroline as a bidentate nitrogen ligand showed high efficacy in this cycloaddition reaction.

A gold-catalyzed cycloisomerization/aerobic oxidation cascade strategy for 2-aryl indenones from 1,5-enynes

A unique gold(i)-catalyzed 5-endo-dig cyclization/aerobic oxidation cascade strategy from 1,5-enyne substrates with molecular oxygen as the oxidant to yield the indenone was described. The reaction mechanism was studied by heavy atom labelling and some related experiments. This method was applied to the formal total synthesis of isoprekinamycin.