352525-91-8

Usage

Uses

Used in Pharmaceutical Industry:
TRANS-2-(4-(TRIFLUOROMETHYL)PHENYL)is used as a key reactant for the preparation of novel chromane, isochromane, thiochromane, or tetrahydroquinoline derivatives. These derivatives serve as glucosylceramide synthase (GCS) inhibitors, which are important targets for the treatment of various diseases, including cancer and neurodegenerative disorders.
Used in Chemical Synthesis:
TRANS-2-(4-(TRIFLUOROMETHYL)PHENYL)is used as a reactant in several chemical reactions, such as microwave-assisted Suzuki-Miyaura cross-coupling, cobalt-catalyzed coupling reactions, and the synthesis of vinylic MIDA boronates. These reactions are crucial for the development of new organic compounds with potential applications in various industries, including pharmaceuticals, materials science, and agrochemicals.
Used in Anticancer Research:
TRANS-2-(4-(TRIFLUOROMETHYL)PHENYL)is used in the synthesis of C2-aryl pyrrolobenzodiazepine antitumor agents. These agents have shown promising results in the treatment of various types of cancer, making them an important area of research in the pharmaceutical industry.
Used in Suzuki-Miyaura Cross-Coupling Reaction:
TRANS-2-(4-(TRIFLUOROMETHYL)PHENYL)is used as a reactant in the Suzuki-Miyaura cross-coupling reaction, a widely employed method for the formation of carbon-carbon bonds in organic synthesis. This reaction is particularly useful for the synthesis of complex molecules, such as those found in pharmaceuticals and advanced materials.

InChI:InChI=1/C9H8BF3O2/c11-9(12,13)8-3-1-7(2-4-8)5-6-10(14)15/h1-6,14-15H/b6-5+

Upstream product

• 705-31-7 4-trifluoromethylphenylacetylene 
• 274-07-7 benzo[1,3,2]dioxaborole 
• 121-43-7 Trimethyl borate 
• 1242770-50-8 (E)-4,4,5,5-tetramethyl-2-(4-trifluoromethylphenyl-vin-1-yl)-1,3,2-dioxaborolane 

Downstream Products

• 1449245-97-9 C₁₇H₂₁F₃O 
• 1449246-20-1 (R,E)-2-(4-(trifluoromethyl)styryl)octan-1-ol 
• 918164-67-7 2,4-bis[4-(trifluoromethyl)phenyl]thiophene 

Relevant academic research and scientific papers

Cu-catalyzed [2 + 2 + 1] cascade annulation of vinyl iodonium salts with elemental sulfur/selenium for the modular synthesis of thiophenes and selenophenes

A [2 + 2 + 1] annulation protocol has been established for the modular synthesis of 2,4-disubstituted thiophenes/selenophenes, with excellent regioselectivity. The reactions have been catalyzed by copper salt with elemental sulfur and selenium serving as

Rate dependence on inductive and resonance effects for the organocatalyzed enantioselective conjugate addition of alkenyl and alkynyl boronic acids to β-indolyl enones and β-pyrrolyl enones

Two key factors bear on reaction rates for the conjugate addition of alkenyl boronic acids to heteroaryl-appended enones: the proximity of inductively electron-withdrawing heteroatoms to the site of bond formation and the resonance contribution of available heteroatom lone pairs to stabilize the developing positive charge at the enone β-position. For the former, the closer the heteroatom is to the enone β-carbon, the faster the reaction. For the latter, greater resonance stabilization of the benzylic cationic charge accelerates the reaction. Thus, reaction rates are increased by the closer proximity of inductive electron-withdrawing elements, but if resonance effects are involved, then increased rates are observed with electron-donating ability. Evidence for these trends in isomeric substrates is presented, and the application of these insights has allowed for reaction conditions that provide improved reactivity with previously problematic substrates.

Transition-Metal-Free Deaminative Vinylation of Alkylamines

The amino group is one of the most fundamental structural motifs in natural products and synthetic chemicals. However, amines potential as effective alkylating agents in organic synthesis is still problematic. A unified strategy has been established for deaminative vinylation of the alkylamines with vinyl boronic acids by C?N bond activation under catalyst-free conditions. The key to the high reactivity is the utilization of pyridinium salt-activated alkylamines, with a base as a promoter. The transformation exhibits good functional group compatibility, and includes inexpensive primary amine feedstocks and amino acids. The proposed method can serve as a powerful synthetic method for late-stage modification of complex compounds. Mechanistic experiments suggest that free radical processes are involved in this system. (Figure presented.).

Enantioselective Multicomponent Condensation Reactions of Phenols, Aldehydes, and Boronates Catalyzed by Chiral Biphenols

Chiral diols and biphenols catalyze the multicomponent condensation reaction of phenols, aldehydes, and alkenyl or aryl boronates. The condensation products are formed in good yields and enantioselectivities. The reaction proceeds via an initial Friedel-Crafts alkylation of the aldehyde and phenol to yield an ortho-quinone methide that undergoes an enantioselective boronate addition. A cyclization pathway was discovered while exploring the scope of the reaction that provides access to chiral 2,4-diaryl chroman products, the core of which is a structural motif found in natural products.

Copper(I)-catalyzed carboxylation of aryl- and alkenylboronic esters

(Chemical Equation Presented) The copper(I)-catalyzed carboxylation reaction of aryl- and alkenylboronic esters proceeded smoothly under CO 2 to give the corresponding carboxylic acid in good yield. This reaction showed wide generality with higher functional group tolerance compared to the corresponding Rh(I)-catalyzed reaction.