401-79-6

Usage

Uses

Used in Pharmaceutical Industry:
3-Methylbenzotrifluoride is used as a solvent and intermediate in the synthesis of pharmaceuticals due to its ability to dissolve a wide range of substances and facilitate chemical reactions necessary for drug production.
Used in Agrochemical Industry:
In the agrochemical sector, 3-Methylbenzotrifluoride serves as an intermediate, aiding in the synthesis of various agrochemicals that are vital for enhancing crop protection and yield.
Used in Polymer Manufacturing:
3-Methylbenzotrifluoride is utilized in the manufacturing of polymers, capitalizing on its chemical properties to produce polymers with specific characteristics required for different applications.
Used in Specialty Chemicals Production:
As a reactant in the production of specialty chemicals, 3-Methylbenzotrifluoride contributes to the creation of unique chemical compounds for specialized uses in various industries, such as fragrances, dyes, and coatings.
Used in High-Temperature Applications:
Owing to its high boiling point and suitability for high-temperature processes, 3-Methylbenzotrifluoride is employed in applications where stability and performance under heat are paramount.

InChI:InChI=1/C8H7F3/c1-6-3-2-4-7(5-6)8(9,10)11/h2-5H,1H3

Upstream product

• 349-75-7 3-(trifluoromethyl)benzyl alcohol 
• 109-06-8 α-picoline 
• 75-63-8 Bromotrifluoromethane 
• 401-78-5 3-bromo-1-trifluoromethylbenzene 
• 917-54-4 methyllithium 
• 1514-87-0 metyhyl chlorodifluoroacetate 
• 625-95-6 3-Iodotoluene 
• 591-17-3 meta-bromotoluene 
• 2923-18-4 sodium 2,2,2-trifluoroacetate 
• 120120-26-5 (trifluoromethyl)triethylsilane 
• 1736-09-0 3-methylphenyl trifluoroacetate 
• 56-23-5 tetrachloromethane 
• 108-88-3 toluene 
• 421-83-0 trifluoromethane sulfonyl chloride 

Downstream Products

• 1861-00-3 deuteriomethyl-benzene 
• 72611-60-0 C₈H₆F₃^(1-) 
• 67192-42-1 2-methyl-4-trifluoromethylnitrobenzene 
• 92891-23-1 2-nitro-3-trifluoromethyl-toluene 
• 87617-21-8 2-(trifluoromethyl)-4-methyl-1-nitrobenzene 
• 96783-80-1 1-Methyl-3-nitro-5-trifluoromethyl-benzene 
• 67169-22-6 2-methyl-4-(trifluoromethyl)benzenamine 
• 87617-23-0 4-methyl-2-trifluoromethylaniline 
• 96100-12-8 3-methyl-5-(trifluoromethyl)aniline 
• 402-23-3 1-bromomethyl-3-trifluoromethylbenzene 
• 54978-36-8 1-iodo-2-methyl-4-(trifluoromethyl)benzene 
• 349-75-7 3-(trifluoromethyl)benzyl alcohol 
• 51579-88-5 N,N-dimethyl-2-oxo-2-(3-(trifluoromethyl)phenyl)acetamide 
• 19519-94-9 3-Trifluormethyl-benzylfluorid 

Relevant academic research and scientific papers

Cross-Coupling through Ag(I)/Ag(III) Redox Manifold

In ample variety of transformations, the presence of silver as an additive or co-catalyst is believed to be innocuous for the efficiency of the operating metal catalyst. Even though Ag additives are required often as coupling partners, oxidants or halide scavengers, its role as a catalytically competent species is widely neglected in cross-coupling reactions. Most likely, this is due to the erroneously assumed incapacity of Ag to undergo 2e? redox steps. Definite proof is herein provided for the required elementary steps to accomplish the oxidative trifluoromethylation of arenes through AgI/AgIII redox catalysis (i. e. CEL coupling), namely: i) easy AgI/AgIII 2e? oxidation mediated by air; ii) bpy/phen ligation to AgIII; iii) boron-to-AgIII aryl transfer; and iv) ulterior reductive elimination of benzotrifluorides from an [aryl-AgIII-CF3] fragment. More precisely, an ultimate entry and full characterization of organosilver(III) compounds [K]+[AgIII(CF3)4]? (K-1), [(bpy)AgIII(CF3)3] (2) and [(phen)AgIII(CF3)3] (3), is described. The utility of 3 in cross-coupling has been showcased unambiguously, and a large variety of arylboron compounds was trifluoromethylated via [AgIII(aryl)(CF3)3]? intermediates. This work breaks with old stereotypes and misconceptions regarding the inability of Ag to undergo cross-coupling by itself.

Cleavage of C(sp3)-F Bonds in Trifluoromethylarenes Using a Bis(NHC)nickel(0) Complex

The first example of the oxidative addition of a C(sp3)-F bond in trifluoromethylarenes to a nickel(0) complex is described. A nickel(0) complex that bears two N-heterocyclic carbene (NHC) ligands of low steric demand is able to cleave C(sp3)-F bonds of trifluoromethylarenes to afford the corresponding trans-difluorobenzyl nickel(II) fluoride complexes. Isolation and characterization studies suggested that the cleavage of the C(sp3)-F bond proceeds via an η2-arene nickel(0) complex. Taking advantage of the reactivity of these nickel(II) fluoride complexes, we developed a catalytic hydrodefluorination of trifluoromethylarenes using hydrosilanes. A computational study indicated that the electron-rich nickel(0) center supported by two relatively small NHC ligands cleaves the C(sp3)-F bond via a syn-SN2′ mechanism.

Cathodic C-H Trifluoromethylation of Arenes and Heteroarenes Enabled by an in Situ-Generated Triflyltriethylammonium Complex

While several trifluoromethylation reactions involving the electrochemical generation of CF3 radicals via anodic oxidation have been reported, the alternative cathodic, reductive radical generation has remained elusive. Herein, the first cathodic trifluoromethylation of arenes and heteroarenes is reported. The method is based on the electrochemical reduction of an unstable triflyltriethylammonium complex generated in situ from inexpensive triflyl chloride and triethylamine, which produces CF3 radicals that are trapped by the arenes on the cathode surface.

Ligand-free trifluoromethylation of iodoarenes by use of 2-Aryl-2-trifluoromethylbenzimidazoline as new trifluoromethylating reagent

N-Methyl 2-aryl-2-trifluoromethylbenzimidazolines were synthesized and utilized in the trifluoromethylation reaction of iodoarenes in the presence of copper(I) salt and base. Iodoarenes bearing electron-donating and electron-withdrawing groups were tolerant to this reaction in the absence of a ligand and gave trifluorotoluene derivatives in good to high yields.

The first nucleophilic C-H perfluoroalkylation of aromatic compounds via (arene)tricarbonylchromium complexes

The first nucleophilic perfluoroalkylation of arenes is based on the arene π-system activation via (η6-arene)tricarbonylchromium complexes. Perfluoroalkyl anions generated from Me3SiRF and a fluoride ion source [Me4N]F exclusively attack the arene ligand under mild conditions. The formed negatively charged analogs of Meisenheimer adducts readily undergo a one-pot oxidation to perfluoroalkyl arenes.

Copper-Promoted Conversion of Aromatic Amines into Trifluoromethylated Arenes: One-Pot Sandmeyer Trifluoromethylation

A simple copper-promoted one-pot Sandmeyer trifluoromethylation of aromatic amines with Langlois’ reagent has been demonstrated. The reaction is performed in mild reaction conditions under an air atmosphere with good substrate scope and functional group compatibility. It provides an alternative and straightforward synthetic approach to access a variety of trifluoromethylated arenes.

Phosphovanadomolybdic acid catalyzed direct C-H trifluoromethylation of (hetero)arenes using NaSO2CF3 as the CF3 source and O2 as the terminal oxidant

A direct C-H trifluoromethylation of (hetero)arenes using NaSO2CF3 (Langlois' reagent) as the CF3 source and O2 as the terminal oxidant has been developed. In the presence of catalytic amounts of phosphovanadomolybdic acids, such as H6PV3Mo9O40, various kinds of substituted benzenes and heteroaromatic compounds could be converted into the corresponding trifluoromethylated products.

Oxygen Activated, Palladium Nanoparticle Catalyzed, Ultrafast Cross-Coupling of Organolithium Reagents

The discovery of an ultrafast cross-coupling of alkyl- and aryllithium reagents with a range of aryl bromides is presented. The essential role of molecular oxygen to form the active palladium catalyst was established; palladium nanoparticles that are highly active in cross-coupling reactions with reaction times ranging from 5 s to 5 min are thus generated in situ. High selectivities were observed for a range of heterocycles and functional groups as well as for an expanded scope of organolithium reagents. The applicability of this method was showcased by the synthesis of the [11C]-labeled PET tracer celecoxib.

DBU-Promoted Trifluoromethylation of Aryl Iodides with Difluoromethyltriphenylphosphonium Bromide

DBU-promoted trifluoromethylation of aryl iodides with difluoromethyltriphenylphosphonium bromide (DFPB) in the presence of copper source is described. In this transformation, DBU not only acts as base to deprotonate the difluoromethyl group in DFPB to generate difluoromethylene phosphonium ylide Ph3P+CF2-, but also converts the difluorocarbene generated from ylide Ph3P+CF2- into trifluoromethyl anion, finally resulting in the trifluoromethylation of aryl iodides. The reactions proceeded smoothly to afford expected products in moderate to good yields.

Trifluoromethylation of haloarenes with a new trifluoro-methylating reagent Cu(O2CCF2SO2F)2

A new trifluoromethylating reagent Cu(O2CCF2SO2F)2, which easily decomposes to generate active CuCF3 species in DMF at room temperature, has been conveniently prepared from inexpensive starting materials on a large scale. This new reagent can be applied to efficiently trifluoromethylate a variety of haloarenes under mild conditions, providing good-to-excellent yields of the desired products.