70097-64-2

Usage

Uses

Used in Pharmaceutical Industry:
3-Benzyloxybenzotrifluoride is used as a starting material for the synthesis of various pharmaceuticals. Its high reactivity and stability contribute to the development of new and effective medications.
Used in Agrochemical Industry:
In the agrochemical sector, 3-Benzyloxybenzotrifluoride serves as a key intermediate in the production of agrochemicals, aiding in the creation of compounds that protect crops and enhance agricultural productivity.
Used in Dye and Pigment Production:
3-Benzyloxybenzotrifluoride is utilized as an intermediate in the manufacturing process of dyes and organic pigments, contributing to the colorfastness and vibrancy of these products in various applications.

InChI:InChI=1/C14H11F3O/c15-14(16,17)12-7-4-8-13(9-12)18-10-11-5-2-1-3-6-11/h1-9H,10H2

Upstream product

• 887144-97-0 Togni's reagent 
• 1484-26-0 3-(benzyloxy)aniline 
• 156682-54-1 3-(benzyloxy)phenylboronic acid 
• 107623-21-2 1-(benzyloxy)-3-iodobenzene 
• 58310-28-4 (Difluoromethyl)triphenylphosphonium bromide 
• 401-78-5 3-bromo-1-trifluoromethylbenzene 
• 100-51-6 benzyl alcohol 
• 98-17-9 3-Trifluoromethylphenol 
• 100-39-0 benzyl bromide 
• 75-45-6 Chlorodifluoromethane 
• 24318-02-3 1-(benzyloxy)-3-chlorobenzene 
• 120120-26-5 (trifluoromethyl)triethylsilane 
• 401-81-0 m-trifluoromethylphenyl iodide 

Downstream Products

• 98-17-9 3-Trifluoromethylphenol 
• 678164-30-2 1-bromo-2-trifluoromethyl-4-(phenylmethoxy)-benzene 

Relevant academic research and scientific papers

Synthesis of ArCF2X and [18F]Ar-CF3via Cleavage of the Trifluoromethylsulfonyl Group

A versatile synthesis of ArCF2X and [18F]Ar-CF3 type compounds from readily available ArCF2SO2CF3 has been developed. Diverse nucleophiles, including weak nucleophiles such as halides (18F-, Cl-, Br-, and I-), RSH, and ROH, could react with ArCF2SO2CF3 efficiently to give the corresponding difluoromethylene products. The control experiments and the Hammett plot indicated that the reaction might proceed through a difluorocarbocation intermediate generated from the steric hindrance-assisted cleavage of the trifluoromethylsulfonyl group.

Cross-Coupling Reactions of Aryl Halides with Primary and Secondary Aliphatic Alcohols Catalyzed by an O,N,N-Coordinated Nickel Complex

A synthesis of alkyl aryl ethers was achieved via the cross-coupling of aryl halides with primary and secondary aliphatic alcohols catalyzed by a bench-stable nickel complex supported by a monoanionic O,N,N-tridentate ligand. This nickel-catalyzed reaction proceeds smoothly in the absence of a phosphine ligand, affording alkyl aryl ethers in moderate to good yields. (Figure presented.).

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.

1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)-promoted decomposition of difluorocarbene and the subsequent trifluoromethylation

Difluorocarbene derived from various carbene precursors could be effectively decomposed by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). This decomposition process was successfully applied in the subsequent trifluoromethylation of a variety of (hetero)aryl iodides without the addition of an external fluoride ion. Mechanistic investigation revealed the detailed difluorocarbene conversion process in which the decomposed difluorocarbene is finally transformed into a fluoride ion and carbon monoxide.

Conversion of aromatic amino into trifluoromethyl groups through a Sandmeyer-type transformation

A novel strategy for aromatic trifluoromethylation by converting amino into trifluoromethyl groups via a Sandmeyer-type reaction is reported. The transformation involves diazotization of the aromatic amines with tert-butyl nitrite and hydrochloric acid to form aryldiazonium chlorides, followed by trifluoromethylation with trifluoromethylsilver at low temperature. Various readily available aromatic amines are smoothly converted under mild conditions. Georg Thieme Verlag Stuttgart. New York.

Copper-mediated radical trifluoromethylation of unsaturated potassium organotrifluoroborates

Copper-mediated trifluoromethylation of unsaturated organotrifluoroborates with the Langlois reagent (NaSO2CF3) and TBHP allows the introduction of trifluoromethyl groups into a variety of organic substructures. The reactions are easy to set up, the conditions are mild and general, and the process provides access to trifluoromethylated alkynes, alkenes, arenes, and heteroarenes in fair to good yields.

Silver-mediated trifluoromethylation of aryldiazonium salts: Conversion of amino group into trifluoromethyl group

A novel strategy for aromatic trifluoromethylation by converting aromatic amino group into CF3 group is reported herein. This method, which can be considered as trifluoromethylation variation of the classic Sandmeyer reaction, uses readily available aromatic amines as starting materials and is performed under mild conditions.

Room-temperature base-free copper-catalyzed trifluoromethylation of organotrifluoroborates to trifluoromethylarenes

An efficient room temperature copper-catalyzed trifluoromethylation of organotrifluoroborates under the base free condition using an electrophilic trifluoromethylating reagent is demonstrated. The corresponding trifluoromethylarenes were obtained in good to excellent yields and the reaction tolerates a wide range of functional groups.

The palladium-catalyzed trifluoromethylation of aryl chlorides

The trifluoromethyl group can dramatically influence the properties of organic molecules, thereby increasing their applicability as pharmaceuticals, agrochemicals, or building blocks for organic materials. Despite the importance of this substituent no general method exists for its installment onto functionalized aromatic substrates. Current methods either require the use of harsh reaction conditions or suffer from a limited substrate scope. Here we report the palladium-catalyzed trifluoromethylation of aryl chlorides under mild conditions, allowing the transformation of a wide range of substrates, including heterocycles, in excellent yields. The process tolerates functional groups such as esters, amides, ethers, acetals, nitriles, and tertiary amines and, therefore, should be applicable to late-stage modifications of advanced intermediates. We have also prepared all the putative intermediates in the catalytic cycle and demonstrated their viability in the process.

N,N-dimethylglycine-promoted ullmann-type coupling reactions of aryl iodides with aliphatic alcohols

The Ullmann-type coupling reactions of aryl iodides and aliphatic alcohols occur at 110°C with N,N-dimethylglycine as the ligand, giving aryl alkyl ethers in good to excellent yields. Georg Thieme Verlag Stuttgart.