402-52-8

Usage

Uses

Used in Pharmaceutical Industry:
4-(Trifluoromethyl)anisole is used as an intermediate in the synthesis of pharmaceutical compounds for its potential to contribute to the development of new drugs. Its unique trifluoromethyl group can enhance the pharmacological properties of drug molecules, improving their efficacy and selectivity.
Used in Agrochemical Industry:
In the agrochemical sector, 4-(Trifluoromethyl)anisole serves as an intermediate in the production of agrochemicals, including pesticides and herbicides. Its incorporation into these compounds can enhance their performance, providing more effective control of pests and weeds in agricultural settings.
Used as a Solvent in Organic Synthesis:
4-(Trifluoromethyl)anisole is utilized as a solvent in various organic synthesis processes due to its ability to dissolve a wide range of compounds and facilitate chemical reactions. Its stability and low reactivity make it a suitable choice for many applications in the synthesis of organic compounds.
Used as a Reagent in Organic Synthesis:
As a reagent, 4-(Trifluoromethyl)anisole plays a crucial role in organic synthesis, particularly in the formation of trifluoromethylated products. Its reactivity can be harnessed to introduce the trifluoromethyl group into target molecules, which can improve their biological activity or chemical properties.

InChI:InChI=1/C8H7F3O/c1-12-7-4-2-6(3-5-7)8(9,10)11/h2-5H,1H3

Upstream product

• 124-41-4 sodium methylate 
• 98-56-6 4-chlorobenzotrifluoride 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 75-63-8 Bromotrifluoromethane 
• 2314-97-8 iodotrifluoromethane 
• 696-62-8 para-iodoanisole 
• 623-12-1 4-chloromethoxybenzene 
• 88986-32-7 methyl 3-oxa-ω-fluorosulfonylperfluoropentanoate 
• 2923-18-4 sodium 2,2,2-trifluoroacetate 
• 421-83-0 trifluoromethane sulfonyl chloride 
• 100-66-3 methoxybenzene 
• 67-56-1 methanol 
• 402-45-9 4-hydroxybenzotrifluoride 
• 74-88-4 methyl iodide 

Downstream Products

• 146539-83-5 2-methoxy-5-(trifluoromethyl)benzaldehyde 
• 240139-82-6 (2-methoxy-5-(trifluoromethyl)phenyl)boronic acid 
• 402-10-8 2-bromo-1-methoxy-4-(trifluoromethyl)benzene 
• 329943-17-1 3-(2-hydroxy-5-trifluoromethyl-benzoyl)-benzonitrile 
• 329943-15-9 3-[2-methoxy-5-(trifluoromethyl)benzoyl]benzonitrile 
• 329943-23-9 [2-(3-cyanobenzoyl)-4-(trifluoromethyl)phenoxy]acetyl chloride 
• 329943-21-7 [2-(3-cyanobenzoyl)-4-(trifluoromethyl)phenoxy]acetic acid 
• 329943-19-3 ethyl [2-(3-cyanobenzoyl)-4-(trifluoromethyl)phenoxy]acetate 
• 791113-36-5 (2-methoxy-5-trifluoromethylphenyl)-phenylmethanol 
• 72083-15-9 (2-methoxy-5-trifluoromethyl-phenyl)-phenyl-methanone 
• 503464-99-1 1-(2-methoxy-5-(trifluoromethyl)phenyl)ethan-1-one 
• 5396-38-3 1-(tert-butyl)-4-methoxybenzene 
• 4864-01-1 2-methoxy-5-(trifluoromethyl)-benzoic acid 
• 1268463-99-5 6-methoxy-2-methyl-3-(trifluoromethyl)benzoic acid 

Relevant academic research and scientific papers

A highly stable all-in-one photocatalyst for aryl etherification: The NiIIembedded covalent organic framework

The efficient conversion of aryl bromides to the corresponding aryl alkyl ethers by dual nickel/photocatalysis has seen great progress, but difficulties of recycling the photosensitizer or nickel complexes cause problems of sustainability. Here, we report the design of a novel, highly stable vinyl bridge 2D covalent organic framework (COF) containing Ni, which combines the role of photosensitizer and reactive site. The as-prepared sp2c-COFdpy-Ni acts as an efficient heterogeneous photocatalyst for C-O cross coupling. The sp2c-COFdpy-Ni can be completely recovered and used repeatedly without loss of activity, overcoming the limitations of the prior methods. Preliminary studies reveal that strong interlayer electron transfer may facilitate the generation of the proposed intermediate sp2c-COFdpy-NiI in a bimolecular and self-sustained manner. This all-in-one heterogeneous photocatalyst exhibits good compatibility of substrates and tolerance of functional groups. The successful attempt to expand the 2D COFs with this new catalyst into photocatalytic organic transformation opens an avenue for photoredox/transition metal mediated coupling reactions.

NOVEL METHOD FOR PRODUCING PERFLUOROALKYLATING AGENTS USING MONOHYDROPERFLUOROALKANE AS STARTING MATERIAL, AND METHOD FOR PRODUCING AROMATIC PERFLUOROALKYL COMPOUND USING THE SAME

PROBLEM TO BE SOLVED: To provide a simple method for producing trifluoromethyltriol borate potassium from trifluoromethane. SOLUTION: There is provided a method for producing a compound represented by the formula [7], comprising: reacting a monohydroperfluoroalkane with a base and trialkyl borate in an organic solvent; and then reacting the reaction solution with triol. [In the formula, RF is an alkyl group such as a linear chain of C1-2, and a perfluoroalkyl group in which all H on C is substituted with F; R6 is H or a C1-2 linear alkyl group, or the like; M may be a metal or the like belonging to Group I, Group II, Group III, Group IV, Group V, Group VI, Group VII, Group VIII, Group IX, Group X, Group XI, Group XII, and Group XIII in the periodic table of elements, and they may be a single substance or a mixture of a plurality of substances and y corresponds to the oxidation number of the substance represented by M.] SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

NOVEL METHOD FOR PRODUCING PERFLUOROALKYLATING AGENTS USING MONOHYDROPERFLUOROALKANE AS STARTING MATERIAL, AND METHOD FOR PRODUCING AROMATIC PERFLUOROALKYL COMPOUND USING THE SAME

PROBLEM TO BE SOLVED: To provide a method for producing an aromatic perfluoroalkyl compound using silylated trifluoromethyl carbinol. SOLUTION: There is provided a method for producing an aromatic perfluoroalkyl compound represented by the general formula [10], in which a compound represented by the formula [9] and a compound represented by the formula [1] are reacted in an organic solvent in the presence of a copper catalyst, a nitrogen ligand and a metal fluoride. R7-X...[9], RF-R7...[10] [In the formula, R7 is an aryl group or the like which may have a substituent; X is F, Cl, Br or I; RF is an alkyl group such as a linear chain of C1-2, and a perfluoroalkyl group in which all H on C is substituted with F; R1 and R2 are each independently H or a C1-2 linear alkyl group, or the like; R1 and R2 may be integrated to form a ring; and R3, R4 and R5 are each independently H or a C1-2 linear alkyl group, or the like.] SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

NOVEL METHOD FOR PRODUCING PERFLUOROALKYLATING AGENTS USING MONOHYDROPERFLUOROALKANE AS STARTING MATERIAL, AND METHOD FOR PRODUCING AROMATIC PERFLUOROALKYL COMPOUNDS USING THE SAME

To provide a simple method for producing silylated trifluoromethylcarbinol from trifluoromethane.SOLUTION: There is provided a method for producing a compound represented by the formula [1], in which the compound is obtained by reacting a monohydroperfluoroalkane, a carbonyl compound, and NaH in an organic solvent and then reacting the reaction solution with a silylating agent. [In the formula, RF is an alkyl group such as a linear chain of C1 to 2, and a perfluoroalkyl group in which all H on C is substituted with F; R1 and R2 are independently alkyl groups such as a linear chain of H or C1 to 2, or the like respectively; R1 and R2 may be integrated to form a ring; and R3, R4 and R5 are independently H or C1 to 2 linear alkyl groups, or the like respectively.]SELECTED DRAWING: None

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.

Mechanistic Insight into Copper-Mediated Trifluoromethylation of Aryl Halides: The Role of CuI

The synthesis, characterization, and reactivity of key intermediates [Cu(CF3)(X)]-Q+ (X = CF3 or I, Q = PPh4) in copper-mediated trifluoromethylation of aryl halides were studied. Qualitative and quantitative studies showed [Cu(CF3)2]-Q+ and [Cu(CF3)(I)]-Q+ were not highly reactive. Instead, a much more reactive species, ligandless [CuCF3] or DMF-ligated species [(DMF)CuCF3], was generated in the presence of excess CuI. On the basis of these results, a general mechanistic map for CuI-promoted trifluoromethylation of aryl halides was proposed. Furthermore, on the basis of this mechanistic understanding, a HOAc-promoted protocol for trifluoromethylation of aryl halides with [Ph4P]+[Cu(CF3)2]- was developed.

Solvated Nickel Complexes as Stoichiometric and Catalytic Perfluoroalkylation Agents**

The acetonitrile-solvated [(MeCN)Ni(C2F5)3]? was prepared in order to compare and contrast its reactivity with the known [(MeCN)Ni(CF3)3]? towards organic electrophiles. Both [(MeCN)Ni(CF3)3]? and [(MeCN)Ni(C2F5)3]? successfully react with aryl iodonium and diazonium salts as well as alkynyl iodonium salts to give fluoroalkylated organic products. Electrochemical analysis of [(MeCN)NiII(C2F5)3]? suggests that, upon electro-oxidation to [(MeCN)nNiIII(C2F5)3], reductive homolysis of a perfluoroethyl radical occurs, with the concomitant formation of [(MeCN)2NiII(C2F5)2]. Catalytic C?H trifluoromethylations of electron-rich arenes were successfully achieved using either [(MeCN)Ni(CF3)3]? or the related [Ni(CF3)4]2?. Stoichiometric reactions of the solvated nickel complexes reveal that “ligandless” nickel is exceptionally capable of serving as reservoir of CF3 groups under catalytically relevant conditions.

Solar-driven tandem photoredox nickel-catalysed cross-coupling using modified carbon nitride

Nickel-catalysed aryl amination and etherification are driven with sunlight using a surface-modified carbon nitride to extend the absorption of the photocatalyst into a wide range of the visible region. In contrast to traditional homogeneous photochemical methodologies, the lower cost and higher recyclability of the metal-free photocatalyst, along with the use of readily available sunlight, provides an efficient and sustainable approach to promote nickel-catalysed cross-couplings. This journal is

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.

Electrochemically Driven, Ni-Catalyzed Aryl Amination: Scope, Mechanism, and Applications

C-N cross-coupling is one of the most valuable and widespread transformations in organic synthesis. Largely dominated by Pd- and Cu-based catalytic systems, it has proven to be a staple transformation for those in both academia and industry. The current study presents the development and mechanistic understanding of an electrochemically driven, Ni-catalyzed method for achieving this reaction of high strategic importance. Through a series of electrochemical, computational, kinetic, and empirical experiments, the key mechanistic features of this reaction have been unraveled, leading to a second generation set of conditions that is applicable to a broad range of aryl halides and amine nucleophiles including complex examples on oligopeptides, medicinally relevant heterocycles, natural products, and sugars. Full disclosure of the current limitations and procedures for both batch and flow scale-ups (100 g) are also described.