709-63-7

Usage

Synthesis

41.6 g of chlorocyclohexane (0.35 mol) were added dropwise to a suspension of 4.65 g of lithium particles (0.68 mol) in 350 g of THF at -55 °C, and an addition time of 2 hours was chosen. After >97% chlorocyclohexane conversion by GC (10 hours), a mixture of 38.3 g of 4-bromotrifluorotoluene (0.170 mol) and 7.0 g of acetonitrile (0.170 mol) was added dropwise at the same temperature for 15 minutes. After stirring for an additional 30 minutes at -50°C, the reaction mixture was slowly thawed to room temperature and subjected to an aqueous workup in a conventional manner. The yield of 4-trifluoromethylacetophenone after distillation was 81%.

Uses

A labelled acetophenone with selective antimycobacterial activity.

General Description

The enantioselective addition of dialkylzinc to 4′-(trifluoromethyl)acetophenone mediated by 1,2-bis(hydroxycamphorsulfonamido)cyclohexenes in the presence of titanium tetraisopropoxide has been investigated. Phosphorescence emission spectra of 4′-(trifluoromethyl)acetophenone has been studied using pulsed source phosphorimetry.

Purification Methods

Purify the ketone by distillation or sublimation in vacuo.[Beilstein 7 IV 1404.]

InChI:InChI=1/C2H4BrF2N/c3-2(4,5)1-6/h1,6H2

Upstream product

• 107496-43-5 1-(4-(trifluoromethyl)phenyl)ethan-1-one O-methyl oxime 
• 75-63-8 Bromotrifluoromethane 
• 99-90-1 para-bromoacetophenone 
• 402-50-6 1-trifluoromethyl-4-vinyl-benzene 
• 55186-75-9 4-trifluoromethyl-α-methylstyrene 
• 1737-26-4 1-(4-trifluorophenyl)ethanol 
• 166189-99-7 2-phenoxy-1-(4-(trifluoromethyl)phenyl)ethan-1-one 
• 383-53-9 2-bromo-1-[4-(trifluoromethyl)phenyl]ethanone 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 455-13-0 4-Iodobenzotrifluoride 
• 104-94-9 4-methoxy-aniline 
• 95-64-7 4-amino-o-xylene 
• 62-53-3 aniline 
• 106-40-1 4-bromo-aniline 

Downstream Products

• 60820-06-6 2-(1-(4-(trifluoromethyl)phenyl)ethylidene)malononitrile 
• 139268-25-0 2-methyl-2-(4-trifluoromethyl-phenyl)-[1,3]dithiane 
• 32120-33-5 trans-4'-(trifluoromethyl)chalcone 
• 132132-57-1 2-(4-trifluoromethyl)phenylquinoline-4-carboxylic acid 
• 389873-26-1 1,3,5-tris[4-(trifluoromethyl)phenyl]pentan-1,5-dione 
• 173543-23-2 (E)-1-(4-trifluoromethylphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 

Relevant academic research and scientific papers

Synthesis of a series of new ruthenium organometallic complexes derived from pyridine-imine ligands and their catalytic activity in oxidation of secondary alcohols

Reactions of pyridine imines [C5H4N-2-C(H)?=?N-C6H4-R] [R?=?H (1), CH3 (2), OMe (3), CF3 (4), Cl (5), Br (6)] with Ru3(CO)12 in refluxing toluene gave the corresponding dinuclear ruthenium carbonyl complexes of the type {μ-η2-CH[(2-C5H4N)(N-C6H4-R)]}2Ru2(CO)4(μ-CO) [R?=?H (7); CH3 (8); OMe (9); CF3 (10); Cl (11); Br (12)]. All six novel complexes were separated by chromatography, and fully characterized by elemental analysis, IR, NMR spectroscopy. Molecular structures of 7, 10, 11, and 12 were determined by X-ray crystal diffraction. Further, the catalytic performance of these complexes was also tested. The combination of {μ-η2-CH[(2-C5H4N)(N-C6H4-R)]}2Ru2(CO)4(μ-CO) and NMO afforded an efficient catalytic system for the oxidation of a variety secondary alcohols.

Selective Activation of Unstrained C(O)-C Bond in Ketone Suzuki-Miyaura Coupling Reaction Enabled by Hydride-Transfer Strategy

A Rh(I)-catalyzed ketone Suzuki-Miyaura coupling reaction of benzylacetone with arylboronic acid is developed. Selective C(O)-C bond activation, which employs aminopyridine as a temporary directing group and ethyl vinyl ketone as a hydride acceptor, occurs on the alkyl chain containing a β-position hydrogen. A series of acetophenone products were obtained in yields up to 75%.

Decatungstate-mediated solar photooxidative cleavage of CC bonds using air as an oxidant in water

With the increasing attention for green chemistry and sustainable development, there has been much interest in searching for greener methods and sources in organic synthesis. However, toxic additives or solvents are inevitably involved in most organic transformations. Herein, we first report the combination of direct utilization of solar energy, air as the oxidant and water as the solvent for the selective cleavage of CC double bonds in aryl olefins. Various α-methyl styrenes, diaryl alkenes as well as terminal styrenes are well tolerated in this green and sustainable strategy and furnished the desired carbonyl products in satisfactory yields. Like heterogeneous catalysis, this homogeneous catalytic system could also be reused and it retains good activity even after repeating three times. Mechanism investigations indicated that both O2- and 1O2 were involved in the reaction. Based on these results, two possible mechanisms, including the electron transfer pathway and the energy transfer pathway, were proposed.

Synthesis and Catalytic Applications of Multinuclear Gold(I)-1,2,3-Triazolylidene Complexes

A series of mono- to trinuclear gold(I) complexes (1–3) supported by oxo-functionalized 1,2,3-triazolylidenes have been prepared. All new compounds were fully characterized by means of 1H and 13C NMR spectroscopy, elemental analyses, and in the case of complexes 1 and 2 by x-ray diffraction. The catalytic performance of the new triazolylidene gold complexes was tested in several hydroelementation and cyclization processes employing a variety of alkynes as starting materials. According to the overall results, the trinuclear complex 3 displayed the highest catalytic activity in all processes, providing good to excellent yields under mild reaction conditions.

One-Pot Chemoenzymatic Conversion of Alkynes to Chiral Amines

A one-pot chemoenzymatic sequential cascade for the synthesis of chiral amines from alkynes was developed. In this integrated approach, just ppm amounts of gold catalysts enabled the conversion of alkynes to ketones (>99%) after which a transaminase was used to catalyze the production of biologically valuable chiral amines in a good yield (up to 99%) and enantiomeric excess (>99%). A preparative scale synthesis of (S)-methylbenzylamine and (S)-4-methoxy-methylbenzylamine from its alkyne form gave a yield of 59 and 92%, respectively, withee> 99%.

Catalytic Aerobic Oxidation of Alkenes with Ferric Boroperoxo Porphyrin Complex; Reduction of Oxygen by Iron Porphyrin

We herein describe the development of a mild and selective catalytic aerobic oxidation process of olefins. This catalytic aerobic oxidation reaction was designed based on experimental and spectroscopic evidence assessing the reduction of atmospheric oxygen using a ferric porphyrin complex and pinacolborane to form a ferric boroperoxo porphyrin complex as an oxidizing species. The ferric boroperoxo porphyrin complex can be utilized as an in-situ generated intermediate in the catalytic aerobic oxidation of alkenes under ambient conditions to form oxidation products that differ from those obtained using previously reported ferric porphyrin catalysis. Moreover, the mild reaction conditions allow chemoselective oxidation to be achieved.

Radical-mediated aerobic oxidation of substituted styrenes and stilbenes

A 2,2-azobis(isobutyronitrile)-catalyzed oxidative cleavage of alkenes with molecular oxygen as the oxidant was described. Carbonyl compounds and oxiranes were obtained in moderate yield under mild conditions. This study provided useful insights into the mechanism of aerobic oxidative cleavage of alkenes.

Promoting charge separation in donor-acceptor conjugated microporous polymers: Via cyanation for the photocatalytic reductive dehalogenation of chlorides

Conjugated microporous polymers (CMPs) have emerged as promising heterogeneous photocatalysts for organic transformations owing to their structural designability and functional versatility. However, limited by the insufficient separation of the photo-generated excitons, their photocatalytic efficiency falls far short of expectations. Herein, we demonstrate a cyanation strategy to promote charge carrier separation in CMPs by selectively incorporating carbazole and cyano groups as electron-donating and electron-withdrawing units, respectively. The resulting CMPs feature π-extended donor (D)-acceptor (A) conjugation structures endowing them with distinct semiconducting properties, in which the efficient charge separation and transfer and wide visible-light absorption are facilitated. Compared to the cyano-free counterpart, the cyano-functionalized CMPs showed superior photocatalytic efficiency as exemplified by photocatalytic reductive dehalogenation of chlorides. More prominently, full recyclability of the designed CMPs as well as catalytic activity for at least ten runs without the loss of catalytic performance in photocatalytic reductive dehalogenation of chlorides demonstrated their robustness and sustainability. This journal is

Photocatalytic Carbinol Cation/Anion Umpolung: Direct Addition of Aromatic Aldehydes and Ketones to Carbon Dioxide

We have developed a new photocatalytic umpolung reaction of carbonyl compounds to generate anionic carbinol synthons. Aromatic aldehydes or ketones reacted with carbon dioxide in the presence of an iridium photocatalyst and 1,3-dimethyl-2-phenyl-2,3-dihydro-1H-benzimidazole (DMBI) as a reductant under visible-light irradiation to furnish the corresponding α-hydroxycarboxylic acids through nucleophilic addition of the resulting carbinol anions to electrophilic carbon dioxide.

Photoinduced Acetylation of Anilines under Aqueous and Catalyst-Free Conditions

A green and efficient visible-light induced functionalization of anilines under mild conditions has been reported. Utilizing nontoxic, cost-effective, and water-soluble diacetyl as photosensitizer and acetylating reagent, and water as the solvent, a variety of anilines were converted into the corresponding aryl ketones, iodides, and bromides. With advantages of environmentally friendly conditions, simple operation, broad substrate scope, and functional group tolerance, this reaction represents a valuable method in organic synthesis.