104201-66-3

Usage

Uses

Used in Pharmaceutical Industry:
(2E)-3-[3-(Trifluoromethyl)phenyl]-2-propenoic acid methyl ester is used as an intermediate in the synthesis of various pharmaceuticals. Its trifluoromethyl group contributes to the development of new drugs with improved pharmacological properties.
Used in Agricultural Industry:
In the agricultural sector, (2E)-3-[3-(Trifluoromethyl)phenyl]-2-propenoic acid methyl ester serves as an intermediate in the production of agrochemicals, potentially enhancing the effectiveness of crop protection agents.
Used in Flavors and Fragrances Production:
This chemical also has potential applications in the creation of flavors and fragrances, where its fruity odor can be utilized to develop new scents and tastes for various consumer products.
Safety Precautions:
It is crucial to handle (2E)-3-[3-(Trifluoromethyl)phenyl]-2-propenoic acid methyl ester with care, as it may pose risks if ingested, inhaled, or comes into contact with skin and eyes. Proper safety measures should be taken to minimize exposure and ensure the well-being of individuals working with (2E)-3-[3-(Trifluoromethyl)phenyl]-2-propenoic acid methyl ester.

Upstream product

• 779-89-5 3-(trifluoromethyl)cinnamic acid 
• 77-78-1 dimethyl sulfate 
• 401-78-5 3-bromo-1-trifluoromethylbenzene 
• 292638-85-8 acrylic acid methyl ester 
• 67-56-1 methanol 
• 401-81-0 m-trifluoromethylphenyl iodide 
• 454-87-5 3-(trifluoromethyl)benzenediazonium tetrafluoroborate 
• 1384879-94-0 (E)-methyl 3-oxo-3-[2-(3-trifluoromethylstyryl)phenyl]propanoate 
• 351-36-0 N-acetyl-3-trifluoromethylbenzenamine 
• 779-89-5 3-(trifluoromethyl)cinnamic acid 
• 98-16-8 3-trifluoromethylaniline 
• 454-89-7 3-Trifluoromethylbenzaldehyde 
• 16695-14-0 Malonic acid monomethyl ester 
• 98-08-8 α,α,α-trifluorotoluene 

Downstream Products

• 104201-78-7 4-Oxo-2-(3-trifluoromethyl-phenyl)-cyclopentane-1,1-dicarboxylic acid 
• 294856-02-3 methyl 3-(3-(trifluoromethyl)phenyl)propanoate 
• 351536-26-0 tert-butyl-dimethyl-[1-trichloromethyl-3-(3-trifluoromethyl-phenyl)-allyloxy]-silane 
• 351536-42-0 (E)-1,1,1-Trichloro-4-(3-trifluoromethyl-phenyl)-but-3-en-2-ol 
• 262268-58-6 (E)-3-(3-(trifluoromethyl)phenyl)acrylaldehyde 

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

Mizoroki-Heck Reaction of Unstrained Aryl Ketones via Ligand-Promoted C-C Bond Olefination

Mizoroki-Heck reaction of unstrained aryl ketone with acrylate/styrene is accomplished via palladium-catalyzed ligand-promoted C-C bond cleavage. Various (hetero)aryl ketones are compatible in the reaction, affording the alkene product in good to excellent yields. Further applications in the late-stage olefination of some drugs, natural products, and fragrance-derived aryl ketones demonstrate the synthetic utility of this protocol. By employing ketone as both the directing group and the leaving group, 1,2-bifunctionalization is achieved via sequential ortho-C-H alkylation/ipso-Heck olefination.

Reduction of Electron-Deficient Alkenes Enabled by a Photoinduced Hydrogen Atom Transfer

Direct hydrogen atom transfer from a photoredox-generated Hantzsch ester radical cation to electron-deficient alkenes has enabled the development of an efficient formal hydrogenation under mild, operationally simple conditions. The HAT-driven mechanism is supported by experimental and computational studies. The reaction is applied to a variety of cinnamate derivatives and related structures, irrespective of the presence of electron-donating or electron-withdrawing substituents in the aromatic ring and with good functional group compatibility. (Figure presented.).

A Photocatalytic Regioselective Direct Hydroaminoalkylation of Aryl-Substituted Alkenes with Amines

A photocatalytic method for the α-selective hydroaminoalkylation of cinnamate esters has been developed. The reaction involves the regioselective addition of α-aminoalkyl radicals generated from aniline derivatives or aliphatic amines to the α-position of unsaturated esters. The scope of aromatic alkenes was extended to styrenes undergoing hydroaminoalkylation with anti-Markovnikov selectivity, which confirms the importance of the aromatic group at the β-position. Simple scale-up is demonstrated under continuous flow conditions, highlighting the practicality of the method.

Formal α-Allylation of Primary Amines by a Dearomative, Palladium-Catalyzed Umpolung Allylation of N-(Aryloxy)imines

N-(Aryloxy)imines, readily accessible by condensation/tautomerization of (pseudo)benzylic primary amines and 2,6-di-tert-butyl-1,4-benzoquinone, undergo efficient allylation to afford a wide range of homoallylic primary amines following hydrolytic workup. Deprotonation of N-(aryloxy)imines generates a delocalized 2-azaallyl anion-type nucleophile that engages in dearomative C-C bond-forming reactions with allylpalladium(II) electrophiles generated from allylic tert-butyl carbonates. This reactivity umpolung enables the formal α-allylation of (pseudo)benzylic primary amines. Mechanistic studies reveal that the apparent regioselectivity of the desired bond-forming event is a convergent process that is initiated by unselective allylation of N-(aryloxy)imines to give several regioisomeric species, which subsequently rearrange via stepwise [1,3]- or concerted [3,3]-sigmatropic shifts, ultimately converging to provide the desired regioisomer of the amine products.

Pd0.09Ce0.91O2-Δ: A sustainable ionic solid-solution precatalyst for heterogeneous, ligand free Heck coupling reactions

A quick and easy method for the preparation of Pd2+ metal ion substituted in ceria, Pd0.09Ce0.91O2-δ solid solution oxide, is described. The Pd0.09Ce0.91O2-δ solid solution oxide was fully characterized by XRD, ICP-OES, BET, XPS, SEM, EDX, TEM, TGA and Raman spectroscopy. All characterization techniques strongly suggested that Pd2+ was successfully incorporated into the lattice structure of ceria. The effect of the reaction conditions on the catalytic properties of the Pd0.09Ce0.91O2-δ solid solution catalyst initially was studied in detail with the model Heck reaction of iodobenzene and methylacrylate to obtain optimum reaction conditions. The Pd0.09Ce0.91O2-δ solid solution catalyst then afforded substituted alkenes in good to excellent yields under these optimum reaction conditions. Steric and electronic effects were also studied, and were found to influence the catalytic activity. Characterization of the used catalyst suggests that Pd2+ in Pd0.09Ce0.91O2-δ is reduced in situ to Pd0 when employed in the Heck cross-coupling reactions. The catalyst was easily recovered by centrifuge and reused three times without significant loss of catalytic efficiency.

Oxidative coupling of Michael acceptors with aryl nucleophiles produced through rhodium-catalyzed C-C bond activation

Utilizing rhodium catalysis, aryl nucleophiles generated via carbon-carbon single bond activation successfully undergo oxidative coupling with Michael acceptors. The reaction scope encompasses a broad range of nucleophiles generated from quinolinyl ketones as well as a series of electron deficient terminal alkenes, illustrating the broad potential of intersecting carbon-carbon bond activation with synthetically useful coupling methodologies. The demonstrated oxidative coupling produces a range of cinnamyl derivatives, several of which are challenging to prepare via conventional routes.

Ligand-controlled regiodivergent palladium-catalyzed decarboxylative allylation reaction to access α,α-difluoroketones

α,α-Difluoroketones possess unique physicochemical properties that are useful for developing therapeutics and probes for chemical biology. To access the α-allyl-α,α-difluoroketone substructure, complementary palladium-catalyzed decarboxylative allylation reactions were developed to provide linear and branched α-allyl-α,α-difluoroketones. For these orthogonal processes, the fluorination pattern of the substrate enabled the ligands to dictate the regioselectivity of the transformations.

(2-Arylethenyl)-1,3,5-triazin-2-amines as a novel histamine H4 receptor ligands

Within the constantly growing number of histamine H4 (H4R) receptor ligands there is a large group of azine derivatives. A series of novel compounds in the group of 4-methylpiperazine-1,3,5-triazine-2-amines were designed and obtained. Considered structures were modified at the triazine 6-position by introduction of variously substituted arylethenyl moieties. Their affinities to histamine H4 receptors were evaluated in radioligand binding assays with use of Sf9 cells, transiently expressing human H4R. Pharmacological studies results allowed to identify 4-[(E)-2-(3-chlorophenyl)ethenyl]-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-amine (Ki Combining double low line 253 nM) as the most potent compound in the present series.

Heck-Matsuda arylation of olefins through a bicatalytic approach: Improved procedures and rationalization

The scope of the palladium-catalyzed Heck-Matsuda reaction, proceeding through the catalytic activation of anilines into the corresponding diazonium salts, has been considerably extended and is now working with deactivated electrophiles. Two different procedures, using catalytic amounts of both palladium and acid, have been optimized allowing the concept of bicatalysis to cover the complete electronic range of anilines. These environmentally friendly procedures proceed under very mild conditions, at room temperature in methanol, and only generate tert-butyl alcohol, water and nitrogen as by-products. Rationalization of reaction outcomes encountered in this work has been discussed with the support of computational studies.