64436-58-4

Usage

Appearance

Yellow to yellow-green liquid

Odor

Strong, aromatic

Usage

Intermediate in the synthesis of pharmaceuticals and agrochemicals, solvent for organic reactions, reagent in organic synthesis, potential precursor to other fluorinated compounds

Importance

Versatile reactivity, functional groups, and as a building block in the chemical industry

Precautions

Handle with care and in accordance with proper safety measures due to reactivity and potential health hazards.

Upstream product

• 197508-91-1 2-methyl-1-(4-(trifluoromethyl)phenyl)propan-1-ol 
• 89635-74-5 C₁₂H₁₁F₃O₂ 
• 67-56-1 methanol 
• 711-33-1 4-trifluoromethyl propiophenone 
• 709-63-7 1-(4-trifluoromethylphenyl)ethanone 
• 74-88-4 methyl iodide 
• 2403-57-8 1-(2-methylprop-1-en-1-yl)pyrrolidine 
• 1301645-90-8 N-isopropyl-4-(trifluoromethyl)benzamide 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 149946-79-2 1-(4'-(trifluoromethyl)phenyl)-allylalcohol 
• 1068-55-9 isopropylmagnesium chloride 
• 329-15-7 4-trifluoromethyl-phenyl acetyl chloride 
• 116332-61-7 N-methoxy-N-methyl-4-trifluoromethylbenzamide 
• 455-24-3 4-trifluoromethylbenzoic acid 

Downstream Products

• 136067-97-5 2-bromo-2-methyl-1-(4-(trifluoromethyl)phenyl)propan-1-one 
• 64436-43-7 α-Isopropyl-α-(α,α,α-trifluoro-p-tolyl)-2-pyridinemethanol 
• 1069130-35-3 C₁₉H₁₄F₃NO₃ 
• 1069130-28-4 C₁₉H₁₅F₃O 
• 359803-67-1 4-(trifluoromethyl)benzoic acid butyl ester 
• 1355254-06-6 C₁₅H₂₁F₃OSi 
• 1364858-50-3 C₁₂H₁₅F₃ 
• 1364859-38-0 C₁₂H₁₅F₃ 
• 1364857-92-0 C₁₂H₁₃F₃ 
• 197508-91-1 2-methyl-1-(4-(trifluoromethyl)phenyl)propan-1-ol 

Relevant academic research and scientific papers

C-C coupling of ketones with methanol catalyzed by a N-heterocyclic carbene-phosphine iridium complex

An N-heterocyclic carbene-phosphine iridium complex system was found to be a very efficient catalyst for the methylation of ketone via a hydrogen transfer reaction. Mild conditions together with low catalyst loading (1 mol%) were used for a tandem process which involves the dehydrogenation of methanol, C=C bond formation with a ketone, and hydrogenation of the new generated double bond by iridium hydride to give the alkylated product. Using this iridium catalyst system, a number of branched ketones were synthesized with good to excellent conversions and yields.

Experimental and Computational Studies of Palladium-Catalyzed Spirocyclization via a Narasaka-Heck/C(sp3or sp2)-H Activation Cascade Reaction

The first synthesis of highly strained spirocyclobutane-pyrrolines via a palladium-catalyzed tandem Narasaka-Heck/C(sp3 or sp2)-H activation reaction is reported here. The key step in this transformation is the activation of a δ-C-H bond via an in situ generated σ-alkyl-Pd(II) species to form a five-membered spiro-palladacycle intermediate. The concerted metalation-deprotonation (CMD) process, rate-determining step, and energy barrier of the entire reaction were explored by density functional theory (DFT) calculations. Moreover, a series of control experiments was conducted to probe the rate-determining step and reversibility of the C(sp3)-H activation step.

External-oxidant-free amino-benzoyloxylation of unactivated alkenes of unsaturated ketoximes with: O -benzoylhydroxylamines

A new copper-catalyzed two-component amino-benzoyloxylation of unactivated alkenes of unsaturated ketoximes with O-benzoylhydroxylamines as the benzoyloxy sources is developed. Chemoselectivity of this method toward amino-benzoyloxylation or oxy-benzoyloxylation of alkenyl ketoximes relies on the position of the tethered olefins, and provides an external-oxidant-free alkene difunctionalization route that directly utilizes O-benzoylhydroxylamines as the benzoyloxy radical precursors and internal oxidants for the divergent synthesis of cyclic nitrones and isoxazolines.

α-Methylation of Ketones with Methanol Catalyzed by Ni/SiO2-Al2O3

α-Methylation of ketones with methanol catalyzed by a cheap and easy to handle Ni/SiO2-Al2O3 was explored. After optimization of the reaction between propiophenone and methanol, the desired product was obtained in 95 % isolated yield. A wide range of ketones was methylated under the optimized conditions (16 examples). This procedure was extended to a three-component cross-benzylation-methylation of acetophenone.

TOLPERISONE ANALOGS AND METHODS OF USE

The present invention is, in part, directed to tolperisone analogs (e.g., compounds of formula (I), (I-a), (I-b), (II), (Il-a), (III), (Ill-a), (ΙΙΙ-b), (III-c), (IV), (IV-a), (V), or (V-a)) and methods of use thereof for the treatment of various conditions including elevated muscle tone and tension (e.g., spasticity, muscle spasm). In one aspect, the tolperisone analogs disclosed herein have an additional substituent at the α-position, which blocks the generation of a β- elimination product.

Silver-promoted cascade radical cyclization of γ,δ-unsaturated oxime esters with P(O)H compounds: synthesis of phosphorylated pyrrolines

A cascade radical cyclization was realized for the first silver-promoted imino-phosphorylation of γ,δ-unsaturated oxime esters, which provided a step-economical and redox-neutral route to access a variety of phosphorylated pyrrolines in good to excellent yields. Moreover, a new bulky trivalent phosphine ligand with a pyrroline motif was obtained through a deoxidation process.

One-Pot Conversion of Allylic Alcohols to α-Methyl Ketones via Iron-Catalyzed Isomerization-Methylation

A one-pot iron-catalyzed conversion of allylic alcohols to α-methyl ketones has been developed. This isomerization-methylation strategy utilized a (cyclopentadienone)iron(0) carbonyl complex as precatalyst and methanol as the C1 source. A diverse range of allylic alcohols undergoes isomerization-methylation to form α-methyl ketones in good isolated yields (up to 84% isolated yield).

Enamines as Surrogates of Alkyl Carbanions for the Direct Conversion of Secondary Amides to α-Branched Ketones

A direct transformation of secondary amides into α-branched ketones with enamines as soft alkylation reagents was developed. In this reaction, enamines serve as surrogates of alkyl carbanions, rather than the conventional enolates equivalents in the Stork's reactions, which allowed for the easy introduction of alkyl groups with electrophilic functional groups. In the presence of 4 ? molecular sieves, the method can be extended to the one-pot coupling of secondary amides with aldehydes to yield ketones. (Figure presented.).

A Coupling Approach for the Generation of α,α-Bis(enolate) Equivalents: Regioselective Synthesis of gem-Difunctionalized Ketones

Regioselective α,α-difunctionalization adjacent to a ketone is a significant synthetic challenge. Here, we present a solution to this problem through the transition-metal-free coupling of esters with geminal bis(boron) compounds. This forms an α,α-bis(enolate) equivalent which can be trapped with electrophiles including alkyl halides and fluorinating agents. This presents an efficient, convergent synthetic strategy for the synthesis of unsymmetrical blocked ketones.

Iron-Catalyzed Methylation Using the Borrowing Hydrogen Approach

A general iron-catalyzed methylation has been developed using methanol as a C1 building block. This borrowing hydrogen approach employs a Kn?lker-type (cyclopentadienone)iron carbonyl complex as catalyst (2 mol %) and exhibits a broad reaction scope. A variety of ketones, indoles, oxindoles, amines, and sulfonamides undergo mono- or dimethylation in excellent isolated yields (>60 examples, 79% average yield).