20754-22-7

Usage

Uses

Used in Fragrance and Flavor Industry:
METHYL 4-TRIFLUOROMETHYLCINNAMATE is used as a synthetic flavoring agent for its sweet, floral scent, enhancing the aroma profiles in various products.
Used in Perfume and Cosmetic Production:
In the cosmetic industry, METHYL 4-TRIFLUOROMETHYLCINNAMATE serves as a key ingredient in perfumes and other cosmetic products, contributing to their distinct fragrances and sensory experiences.
Used as a Pharmaceutical Intermediate:
METHYL 4-TRIFLUOROMETHYLCINNAMATE is utilized as an intermediate in the synthesis of pharmaceuticals, playing a crucial role in the development of new medications.
Used in Agrochemical Synthesis:
METHYL 4-TRIFLUOROMETHYLCINNAMATE is also used as an intermediate in the production of agrochemicals, contributing to the development of effective pest control solutions.
Used in Antimicrobial and Anti-Fungal Applications:
Due to its antimicrobial and antifungal properties, METHYL 4-TRIFLUOROMETHYLCINNAMATE is employed in various applications to inhibit the growth of harmful microorganisms.
Used in Agricultural Insecticides and Acaricides:
METHYL 4-TRIFLUOROMETHYLCINNAMATE is used as an insecticide and acaricide in agriculture to protect crops from pests and mites, ensuring higher yields and crop quality.
Used in Organic Electronics and Optoelectronics:
With its potential applications in the field of organic electronics and optoelectronic devices, METHYL 4-TRIFLUOROMETHYLCINNAMATE is a component in the development of advanced electronic and photonic technologies.

InChI:InChI=1/C11H9F3O2/c1-16-10(15)7-4-8-2-5-9(6-3-8)11(12,13)14/h2-7H,1H3/b7-4+

Upstream product

• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 79-20-9 acetic acid methyl ester 
• 455-13-0 4-Iodobenzotrifluoride 
• 292638-85-8 acrylic acid methyl ester 
• 116-54-1 dichloroacetic acid methyl ester 
• 2062-26-2 3-<4'-(trifluoromethyl)phenyl>-2-propenoic acid 
• 77-78-1 dimethyl sulfate 
• 67-56-1 methanol 
• 96-32-2 bromoacetic acid methyl ester 
• 183801-13-0 3-(4-(trifluoromethyl)phenyl)propiolaldehyde 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 1323307-38-5 (E)-methyl 3-oxo-3-(2-styrylphenyl)propanoate 
• 1384879-87-1 (E)-methyl 3-oxo-3-[2-(4-trifluoromethylstyryl)phenyl]propanoate 
• 128796-39-4 4-trifluoromethylphenylboronic acid 

Downstream Products

• 20754-22-7 methyl (Z)-3-(4-trifluoromethylphenyl)acrylate 
• 125617-18-7 3-(4-trifluoromethylphenyl)-2-propen-1-ol 
• 184360-95-0 (E)-4-((p-trifluoromethyl)phenyl)but-3-enoic acid 
• 849442-21-3 methyl 3-(4-(trifluoromethyl)phenyl)propanoate 

Relevant academic research and scientific papers

A cross-linked reverse micelle-encapsulated palladium catalyst

Cross-linked reverse micelle-palladium catalysts are effective and stable cross-coupling catalysts; cross-linking is crucial for stability. The Royal Society of Chemistry 2005.

Phosphine-Functionalized Chitosan Microparticles as Support Materials for Palladium Nanoparticles in Heck Reactions

Herein, we investigated the activation and stabilization of Pd nanoparticles using microparticles of chitosan-functionalized with phosphine moieties. The catalytic activity of the prepared material was assessed in a series of Heck reactions, which demonst

Oxoammonium-Mediated Allylsilane–Ether Coupling Reaction

A new C(sp3)?H functionalization reaction consisting of the oxidative α-allylation of allyl- and benzyl- methyl ethers has been developed. The C?C coupling could be carried out under mild conditions thanks to the use of cheap and green oxoammonium salts. The scope of the reaction was studied over 27 examples, considering the nature of the substituents on the two coupling partners.

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.

Design and synthesis of bitopic 2-phenylcyclopropylmethylamine (pcpma) derivatives as selective dopamine d3 receptor ligands

2-Phenylcyclopropylmethylamine (PCPMA) analogues have been reported as selective serotonin 2C agonists. On the basis of the same scaffold, we designed and synthesized a series of bitopic derivatives as dopamine D3R ligands. A number of these new compounds show a high binding affinity for D3R with excellent selectivity. Compound (1R,2R)-22e and its enantiomer (1S,2S)-22e show a comparable binding affinity for the D3R, but the former is a potent D3R agonist, while the latter acts as an antagonist. Molecular docking studies revealed different binding poses of the PCPMA moiety within the orthosteric binding pocket of the D3R, which might explain the different functional profiles of the enantiomers. Compound (1R,2R)-30q shows a high binding affinity for the D3R (Ki = 2.2 nM) along with good selectivity, as well as good bioavailability and brain penetration properties in mice. These results reveal that the PCPMA scaffold may serve as a privileged scaffold for the design of aminergic GPCR ligands.

Enantioenriched Methylene-Bridged Benzazocanes Synthesis by Organocatalytic and Superacid Activations

Achieving in a straightforward way the synthesis of enantioenriched elaborated three-dimensional molecules related to bioactive natural products remains a long-standing quest in organic synthesis. Enantioselective organocatalysis potentially offers a uniq

Discovery of 3,4,6-Trisubstituted Piperidine Derivatives as Orally Active, Low hERG Blocking Akt Inhibitors via Conformational Restriction and Structure-Based Design

A series of 3,4-disubstituted piperidine derivatives were obtained based on a conformational restriction strategy and a lead compound, A12, that exhibited potent in vitro and in vivo antitumor efficacies; however, obvious safety issues limited its further development. Thus, systematic exploration of the structure-activity relationship of compound A12, involving the phenyl group, hinge-linkage, and piperidine moiety, led to the discovery of the superior 3,4,6-trisubstituted piperidine derivative E22. E22 showed increased potency in Akt1 and cancer cell inhibition, remarkably reduced human ether-a-go-go-related gene blockage, and significantly improved safety profiles. Compound E22 also exhibited good kinase selectivity, had a good pharmacokinetic profile, and displayed very potent in vivo antitumor efficacy, with over 90% tumor growth inhibition in the SKOV3 xenograft model. Further mechanistic studies were conducted to demonstrate that compound E22 could significantly inhibit the phosphorylation of proteins downstream of Akt kinase in cells and tumor tissue from the xenograft model.

4-Aryl Pyrrolidines as a Novel Class of Orally Efficacious Antimalarial Agents. Part 1: Evaluation of 4-Aryl- N-benzylpyrrolidine-3-carboxamides

Identification of novel chemotypes with antimalarial efficacy is imperative to combat the rise of Plasmodium species resistant to current antimalarial drugs. We have used a hybrid target-phenotype approach to identify and evaluate novel chemotypes for malaria. In our search for drug-like aspartic protease inhibitors in publicly available phenotypic antimalarial databases, we identified GNF-Pf-4691, a 4-aryl-N-benzylpyrrolidine-3-carboxamide, as having a structure reminiscent of known inhibitors of aspartic proteases. Extensive profiling of the two terminal aryl rings revealed a structure-activity relationship in which relatively few substituents are tolerated at the benzylic position, but the 3-aryl position tolerates a range of hydrophobic groups and some heterocycles. Out of this effort, we identified (+)-54b (CWHM-1008) as a lead compound. 54b has EC50 values of 46 and 21 nM against drug-sensitive Plasmodium falciparum 3D7 and drug-resistant Dd2 strains, respectively. Furthermore, 54b has a long half-life in mice (4.4 h) and is orally efficacious in a mouse model of malaria (qd; ED99 ～ 30 mg/kg/day). Thus, the 4-aryl-N-benzylpyrrolidine-3-carboxamide chemotype is a promising novel chemotype for malaria drug discovery.