1891-90-3

Usage

Chemical Properties

White to light yellow crystal powde

InChI:InChI=1/C8H6F3NO/c9-8(10,11)6-3-1-5(2-4-6)7(12)13/h1-4H,(H2,12,13)

Upstream product

• 329-15-7 4-trifluoromethyl-phenyl acetyl chloride 
• 455-13-0 4-Iodobenzotrifluoride 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 1448887-34-0 methyl 3-oxo-3-(4-(trifluoromethyl)phenyl) propanedithioate 
• 1171113-63-5 2-bromo-1-(5-phenyloxazol-2-yl)ethanone 
• 131472-28-1 4-trifluoromethylbenzamidine 
• 339-59-3 4-(trifluoromethyl)benzoic acid hydrazide 
• 91888-96-9 N-(tert-butyl)-4-(trifluoromethyl)benzamide 
• 201230-82-2 carbon monoxide 
• 619-58-9 4-iodobenzoic acid 
• 349-95-1 4-(trifluoromethyl)benzylic alcohol 
• 872-85-5 pyridine-4-carbaldehyde 
• 455-24-3 4-trifluoromethylbenzoic acid 

Downstream Products

• 117720-87-3 p-trifluoromethylbenzamido-1 (cyclohexene-1 yl)-2 cyclohexene 
• 125931-36-4 4-(trifluoromethyl)benzoyl isocyanate 
• 258346-49-5 2-[2-[4-trifluoromethylphenyl)-5-methyl-1,3-oxazol-4-yl]acetic acid methyl ester 
• 22091-40-3 4-(chloromethyl)-2-(4-(trifluoromethyl)phenyl)oxazole 
• 23794-77-6 N-(4-trifluoromethylphenyl)-O-methylcarbamate 
• 293306-94-2 4-phenyl-2-(4-(trifluoromethyl)phenyl)oxazole 
• 583883-82-3 4-methyl-2-(4-trifluoromethyl-phenyl)-oxazole-5-carboxylic acid methyl ester 
• 455-18-5 4-CF₃C₆H₄CN 
• 851224-79-8 5-(4-trifluoromethylphenyl)[1,3,4]oxathiazol-2-one 
• 334015-34-8 ethyl 2-ethyl-3-[3-[4-(trifluoromethyl)benzoylaminomethyl]-4-methoxyphenyl]propanoate 

Relevant academic research and scientific papers

Cu(II)–metformin immobilized on graphene oxide: an efficient and recyclable catalyst for the Beckmann rearrangement

Abstract: In this study, for the first time, the copper(II) nanoparticles (NPs) have been immobilized on metformin-functionalized graphene oxide and then its catalytic applications have been investigated in synthesis of amides from aldoximes (Beckmann rearrangement). The chemical structure of prepared catalyst has been characterized by various analyses like FT-IR, TGA, TEM, SEM, EDX, and ICP. All analyses confirm the successful and stable immobilization of copper NPs on functionalized graphene oxide. This synthesized heterogeneous nanocatalyst showed excellent catalytic activity with high product yields and short reaction times. Also, the suggested catalyst could be recycled ten times without a drastic decrease in its catalytic activity. Graphic abstract: [Figure not available: see fulltext.].

Investigation of Nitrile Hydration Chemistry by Two Transition Metal Hydroxide Complexes: Mn-OH and Ni-OH Nitrile Insertion Chemistry

Herein we describe the synthesis of a series of nickel complexes, including the formation of [(iPrPNHP)Ni(PMe3)][BPh4] (iPrPNHP = HN(CH2CH2(PiPr2))2). The ability of this phosphine complex to perform the 1,2-addition of H2O to produce the Ni-OH species [(iPrPNHP)NiOH][BPh4] has been investigated. The nucleophilicity of the hydroxide moiety of both [(iPrPNHP)NiOH][BPh4] and the previously reported (iPrPNHP)MnOH(CO)2 was investigated through the hydration of aryl and alkyl nitriles, leading to the formation of a number of metal carboxamide (RC(O)NH-) bonds. This reactivity generated complexes with the general structures of [(iPrPNHP)Ni(NHC(O)R)][BPh4] for nickel and (iPrPNHP)Mn(NHC(O)R)(CO)2 for manganese. Under catalytic conditions, the hydration of nitriles using nickel complexes yielded only a single turnover. However, (iPrPNHP)MnOH(CO)2 produced several turnovers, and the reaction conditions were probed for optimization.

Half-sandwich ruthenium complexes with oxygen–nitrogen mixed ligands as efficient catalysts for nitrile hydration reaction

Three ruthenium(II) p-cymene complexes containing oxygen–nitrogen mixed ligands [Ru(p-cymene)LCl] [HL = 2-(4,5-dihydrooxazol-2-yl)phenol (2a); HL = 2-(4,5-dihydrothiazol-2-yl)phenol (2b); HL = 2-(5,6-dihydro-4H-1,3-oxazin-2-yl)phenol (2c)] have been synthesized and characterized. All half-sandwich ruthenium complexes were fully characterized by 1H and 13C NMR spectra, elemental analyses and infrared spectrometry. The molecular structure of ruthenium complex 2c was further confirmed by single-crystal X-ray diffraction methods. Furthermore, these half-sandwich ruthenium complexes are active catalysts for the hydration of nitriles to amides in the presence of sodium hydroxide in isopropanol.

Synthesis of a copper(ii) complex covalently anchoring a (2-iminomethyl)phenol moiety supported on HAp-encapsulated-α-Fe2O3 as an inorganic-organic hybrid magnetic nanocatalyst for the synthesis of primary and secondary amides

A novel hydroxyapatite-encapsulated-α-Fe2O3-based Cu(ii) organic-inorganic hybrid (interphase) catalyst was prepared. The prepared nanocatalyst provided an efficient, useful and green method for the oxidative amidation of aromatic aldehydes with ammonium hydrochloride and aniline hydrochloride, in short reaction times and good yields. The magnetic nature of the catalyst led to its easy recovery by an external magnetic field and convenient reuse.

Nitrogen Atom Transfer Catalysis by Metallonitrene C?H Insertion: Photocatalytic Amidation of Aldehydes

C?H amination and amidation by catalytic nitrene transfer are well-established and typically proceed via electrophilic attack of nitrenoid intermediates. In contrast, the insertion of (formal) terminal nitride ligands into C?H bonds is much less developed and catalytic nitrogen atom transfer remains unknown. We here report the synthesis of a formal terminal nitride complex of palladium. Photocrystallographic, magnetic, and computational characterization support the assignment as an authentic metallonitrene (Pd?N) with a diradical nitrogen ligand that is singly bonded to PdII. Despite the subvalent nitrene character, selective C?H insertion with aldehydes follows nucleophilic selectivity. Transamidation of the benzamide product is enabled by reaction with N3SiMe3. Based on these results, a photocatalytic protocol for aldehyde C?H trimethylsilylamidation was developed that exhibits inverted, nucleophilic selectivity as compared to typical nitrene transfer catalysis. This first example of catalytic C?H nitrogen atom transfer offers facile access to primary amides after deprotection.

Cu(II)-promoted oxidative C-N bond cleavage of N-benzoylamino acids to primary aryl amides

A novel protocol for CuCl2-promoted oxidative C-N bond cleavage of N-benzoyl amino acids was developed. It is the first example of using accessible amino acid as an ammonia synthetic equivalent for the synthesis of primary aryl amides via CuCl2-promoted oxidative C-N bond cleavage reaction. The present protocol shows excellent functional group tolerance and provides an alternative method for the synthetic of primary aryl amides in 84-96% yields.

Hydrosilylative reduction of primary amides to primary amines catalyzed by a terminal [Ni-OH] complex

A terminal [Ni-OH] complex1, supported by triflamide-functionalized NHC ligands, catalyzes the hydrosilylative reduction of a range of primary amides into primary amines in good to excellent yields under base-free conditions with key functional group tolerance. Catalyst1is also effective for the reduction of a variety of tertiary and secondary amides. In contrast to literature reports, the reactivity of1towards amide reduction follows an inverse trend,i.e., 1° amide > 3° amide > 2° amide. The reaction does not follow a usual dehydration pathway.

Deoxygenative hydroboration of primary, secondary, and tertiary amides: Catalyst-free synthesis of various substituted amines

Transformation of relatively less reactive functional groups under catalyst-free conditions is an interesting aspect and requires a typical protocol. Herein, we report the synthesis of various primary, secondary, and tertiary amines through hydroboration of amides using pinacolborane under catalyst-free and solvent-free conditions. The deoxygenative hydroboration of primary and secondary amides proceeded with excellent conversions. The comparatively less reactive tertiary amides were also converted to the corresponding N,N-diamines in moderate yields under catalyst-free conditions, although alcohols were obtained as a minor product.

Ring Opening/Site Selective Cleavage in N-Acyl Glutarimide to Synthesize Primary Amides

A LiOH-promoted hydrolysis selective C-N cleavage of twisted N-acyl glutarimide for the synthesis of primary amides under mild conditions has been developed. The reaction is triggered by a ring opening of glutarimide followed by C-N cleavage to afford primary amides using 2 equiv of LiOH as the base at room temperature. The efficacy of the reactions was considered and administrated for various aryl and alkyl substituents in good yield with high selectivity. Moreover, gram-scale synthesis of primary amides using a continuous flow method was achieved. It is noted that our new methodology can apply under both batch and flow conditions for synthetic and industrial applications.

Unlocking Amides through Selective C–N Bond Cleavage: Allyl Bromide-Mediated Divergent Synthesis of Nitrogen-Containing Functional Groups

We report a new set of reactions based on the unlocking of amides through simple treatment with allyl bromide, creating a common platform for accessing a diverse range of nitrogen-containing functional groups such as primary amides, sulfonamides, primary amines, N-acyl compounds (esters, thioesters, amides), and N-sulfonyl esters. The method has potential industrial applicability, as demonstrated through gram-scale syntheses in batch and in a continuous flow system.