352-03-4

Usage

Uses

Used in Pharmaceutical Production:
3-(4-FLUORO-PHENYL)-ACRYLIC ACID ETHYL ESTER is utilized as a key intermediate in the synthesis of pharmaceuticals. Its unique structure allows it to be a building block for the development of new drugs, particularly those targeting specific biological pathways or receptors.
Used in Organic Synthesis:
In the field of organic synthesis, 3-(4-FLUORO-PHENYL)-ACRYLIC ACID ETHYL ESTER serves as a versatile reagent and precursor for the creation of a variety of organic compounds. Its 4-fluoro-phenyl group can be further modified or used to form new chemical entities with specific properties.
Used in Polymer and Resin Manufacturing:
3-(4-FLUORO-PHENYL)-ACRYLIC ACID ETHYL ESTER is also employed in the production of polymers and resins, where its chemical structure can contribute to the desired physical and chemical characteristics of the final product, such as improved stability, reactivity, or specific interactions with other materials.
Used in Organic Electronics and Optoelectronics:
3-(4-FLUORO-PHENYL)-ACRYLIC ACID ETHYL ESTER's potential applications extend to the field of organic electronics and optoelectronics, where its electronic properties, influenced by the 4-fluoro-phenyl group, may be harnessed to develop new materials for electronic devices, sensors, or light-emitting applications.

InChI:InChI=1/C11H11FO2/c1-2-14-11(13)8-5-9-3-6-10(12)7-4-9/h3-8H,2H2,1H3/b8-5+

Upstream product

• 459-57-4 4-fluorobenzaldehyde 
• 105-36-2 ethyl bromoacetate 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 64-17-5 ethanol 
• 74929-23-0 3-(4-fluorophenyl)-2-propynal 
• 459-32-5 (E)-4-fluorocinnamic acid 
• 456-22-4 4-Fluorobenzoic acid 
• 352-13-6 4-flourophenylmagnesium bromide 
• 623-47-2 propynoic acid ethyl ester 
• 141-82-2 malonic acid 
• 462-06-6 fluorobenzene 
• 140-88-5 ethyl acrylate 
• 2033-24-1 cycl-isopropylidene malonate 
• 459-32-5 4-fluorocinnamic acid 

Downstream Products

• 42122-47-4 2,3-dibromo-3-(4-fluoro-phenyl)-propionic acid ethyl ester 
• 852661-24-6 C₂₈H₃₈FN₃O₃ 
• 852660-80-1 C₂₈H₄₀FN₃O₂ 
• 852660-63-0 C₂₇H₃₅FN₂O₄ 
• 852660-35-6 (1R,2S)-[2-({tert-butoxycarbonyl-[3-(4-fluoro-phenyl)-propyl]amino}-methyl)-cyclohexyl]-carbamic acid benzyl ester 
• 852661-45-1 benzyl (1R,2S,4R)-4-amino-2-(((3-(4-fluorophenyl)propyl)(propyl)amino)methyl)-cyclohexylcarbamate 
• 852661-32-6 N-({(1S,2R)-2-[[3-(4-fluorophenyl)propyl]amino]cyclohexyl}methyl)-N'-[3-(1-methyl-1H-tetrazol-5-yl)phenyl]urea 
• 852661-30-4 N-{(1R,3S,4R)-3-{[[3-(4-fluorophenyl)propyl](methyl)amino]methyl}-4-[({[4-methyl-1,3-thiazol-2-yl]amino}carbonyl)amino]cyclohexyl}-N-methylacetamide 
• 852661-31-5 N-{(1S,3S,4R)-3-{[[3-(4-fluorophenyl)propyl](methyl)amino]methyl}-4-[({[4-methyl-1,3-thiazol-2-yl]amino}carbonyl)amino]cyclohexyl}-N-methylacetamide 
• 852660-78-7 C₂₉H₃₉FN₂O₄ 
• 852661-42-8 benzyl {(7S,8R)-7-[((3-((4-fluorophenyl)propyl)(propyl)amino)methyl)]-1,4-dioxa-spiro[4.5]dec-8-yl}-carbamate 
• 852661-39-3 N-({(1S,2R)-2-[[3-(4-fluorophenyl)propyl](methyl)amino]cyclohexyl}methyl)-N'-[3-(1-methyl-1H-tetrazol-5-yl)phenyl]urea 
• 852660-81-2 C₃₀H₄₂FN₃O₃ 
• 852660-60-7 N-((1R,3R,4S)-3-({[(3-acetylphenyl)amino]carbonyl}amino)-4{[3-(4-fluorophenyl)propyl(methyl)amino]methyl}cyclohexyl)-N-methylacetamide 

Relevant academic research and scientific papers

Photoinduced Regioselective Olefination of Arenes at Proximal and Distal Sites

The Fujiwara-Moritani reaction has had a profound contribution in the emergence of contemporary C-H activation protocols. Despite the applicability of the traditional approach in different fields, the associated reactivity and regioselectivity issues had

Identification of (6S)-cyclopropyl-6,7-dihydropyrazolo[1,5-a]pyrazine-5(4H)-carboxamines as new HBV capsid assembly modulators

GYH2-18 is a type II HBV CAM with 6,7-dihydropyrazolo[1,5-a]pyrazine-5(4H)-carboxamine (DPPC) skeleton discovered by Roche INC. A series of GYH2-18 derivatives were designed, synthesized and evaluated for their anti-HBV activity. Two compounds 2f and 3k exhibited excellent anti-HBV activity, low cytotoxicity and accepted oral PK profiles. Chiral separation of 2f and 3k was conducted successfully, and (6S)-cyclopropyl DPPC isomers 2f-1, 2f-3, 3k-1 and 3k-3 were identified to be much more active than the corresponding (6R)-ones. The preliminary structure-activity relationship, particle gel assay and molecular modeling studies were also discussed, which provide useful indications for guiding the further rational design of new (6S)-cyclopropyl DPPC analogues.

A One-Pot Synthesis of α,β-Unsaturated Esters From Esters

A convenient method for reductive Horner–Wadsworth–Emmons (HWE) olefination is described. The E-selective HWE homologation of various esters to α,β-unsaturated esters was readily achieved and gave the desired products in good-to-moderate yields under mild conditions. The one-pot reaction proceeds through an in situ generated aldehyde, formed via the partial reduction of an ester with lithium diisobutyl-t-butoxyaluminum hydride. The formation of cyclized metal acetal and subsequent decompose to the aldehyde for the olefination was found to be a crucial step in this C2-carbon homologation protocol.

Hypervalent iodine(iii) induced oxidative olefination of benzylamines using Wittig reagents

We have developed hypervalent iodine(iii) induced oxidative olefination of primary and secondary benzylamines using 2C-Wittig reagents, which provides easy access to α,β-unsaturated esters. Mild reaction conditions, good to excellent yields with high (E) selectivity, and a broad substrate scope are the key features of this reaction. We have successfully carried out the gram-scale synthesis of α,β-unsaturated esters.

Photoinduced Oxidative Alkoxycarbonylation of Alkenes with Alkyl Formates

A photoinduced oxidative alkoxycarbonylation of alkenes initiated by intermolecular addition of alkoxycarbonyl radicals has been demonstrated. Employing alkyl formates as alkoxycarbonyl radical sources, a range of α,β-unsaturated esters were obtained with good regioselectivity and E selectivity under ambient conditions.

Oxime ligands for Pd catalysis of the Mizoroki–Heck reaction, Suzuki–Miyaura coupling & annulation reactions

Monodentate and bidentate chelating oximes are readily available ligands for the Pd catalysis of the Mizoroki–Heck reaction and the Suzuki coupling. High yields were obtained in the Suzuki coupling in aqueous dioxane with TBABr as additive. The oximes can be easily synthesized from the corresponding ketones or aldehydes and thus provide a very large number of nitrogen-based ligands. They have the advantage of not undergoing oxidative degradation, common for phosphine ligands. Chelating oximes with Pd(OAc)2, activate aryl iodides to give high yields of the substitution products in the Mizoroki–Heck reactions as well as the Suzuki coupling. Acetophenone oxime ligand with Pd(OAc)2, catalyzed the reaction of aryl iodides with 1,2-disubstituted alkenes in moderate to high yields. As a test example, the LaRock indole annulation and synthesis of isocoumarin were achieved with acetophenone oxime ligand and Pd(OAc)2 in high yields.

Bimetallic nano alloy architecture on a special polymer: Ni or Cu merged with Pd for the promotion of the Mizoroki–Heck reaction and the Suzuki–Miyaura coupling

Abstract: Novel Ni-Pd and Cu-Pd bimetallic nano alloys was designed and heterogenized on the highly robust ABPBI [poly(2,5-benzimidazole)] polymer in high yields using NaBH4 as reducing agent. These were versatile ligand free catalysts for the Mizoroki–Heck reaction and Suzuki–Miyaura coupling. The bimetallic Ni-Pd-ABPBI catalyst for the Mizoroki–Heck reaction of 4-iodo anisole could be recycled 5 times with high yields. Aryl bromides could also be activated for the Mizoroki–Heck reaction using Cu-Pd-ABPBI NP catalysts, with moderate yields. Graphic abstract: Synopsis Novel bimetallic Ni-Pd and Cu-Pd nano alloys, heterogenized on the robust ABPBI [poly(2,5-benzimidazole)] polymer using NaBH4 as reducing agent, is described. These were versatile ligand free, noble metal conservative catalysts, for the Mizoroki–Heck reaction and the Suzuki–Miyaura coupling. Aryl bromides were activated for the Mizoroki–Heck reaction using the Cu-Pd-ABPBI catalyst.[Figure not available: see fulltext.]

Palladium Nanoparticles Anchored on Magnesium Organosilicate: An Effective and Selective Catalyst for the Heck Reaction

A new and effective palladium catalyst supported on a magnesium organosilicate for application in the Heck reaction is presented. A group of compounds comprising 22 examples were synthesized in moderate to high yields (up to 99%) within a short time. The palladium supported on magnesium organosilicate catalyst was characterized as an amorphous solid by SEM, containing around 33% of palladium inside the solid, and even with this low quantity of palladium, the catalyst was very efficient in the Heck reaction. Besides, based on the Scherrer equation, the crystallite size of the synthesized palladium nanoparticles was ultrasmall (around 1.3 nm). This strategy is a simple and efficient route for the formation of C-C bonds via the Heck cross-coupling reaction.

Thermal proteome profiling efficiently identifies ribosome destabilizing oxazolidinones

Identifying the targets of bioactive small molecules is a challenging endeavor for which no general solution currently exists. Classical affinity purification experiments suffer from the need to functionalise a bioactive compound and link it to a solid support, which may interfere with target binding. A modern mass spectrometry-based proteomics technique that has partially circumvented this problem is thermal proteome profiling (TPP), which determines the effect of an unmodified small molecule on the thermal stability of the whole proteome simultaneously. Here, we use TPP to identify the mode-of-action of a newly-discovered autophagy inhibitor based on oxazolidinones often employed as chiral auxiliaries. Surprisingly, a significant portion of all ribosomal proteins were found to be destabilized by the inhibitor, highlighting the utility of this technology for determining a challenging mode-of-action.

Electrochemical Generation of a Nonstabilized Azomethine Ylide: Access to Substituted N-Heterocycles

Azomethine ylides are fascinating 1,3-dipoles for [3 + 2] cycloaddition reactions toward the construction ofN-heterocycles. Herein, an efficient and environmentally benign electrochemical approach for the generation of a nonstabilized azomethine ylide has been established under metal-free and external oxidant-free conditions. The resulting 1,3-dipole undergoes a [3 + 2] cycloaddition reaction with olefins. This electrosynthetic methodology indulges a straightforward and facile approach for the construction of substituted pyrrolidines.