351500-12-4

Usage

Uses

Used in Pharmaceutical Industry:
1H-Indole-1-carboxylic acid, 5-(trifluoromethyl)-, 1,1-dimethylethyl ester is utilized as a key intermediate in the development and production of various pharmaceuticals. Its stability and reactivity make it an ideal candidate for the synthesis of complex drug molecules, contributing to the advancement of novel treatments and therapeutics.
Used in Agrochemical Industry:
In the agrochemical sector, 1H-Indole-1-carboxylic acid, 5-(trifluoromethyl)-, 1,1-dimethylethyl ester is employed as a vital component in the creation of pesticides and other agricultural chemicals. Its role in the synthesis of these products is instrumental in enhancing crop protection strategies and ensuring food security.
Used in Organic Synthesis:
1H-Indole-1-carboxylic acid, 5-(trifluoromethyl)-, 1,1-dimethylethyl ester is also used as a reagent in organic synthesis for the preparation of a wide array of chemical compounds. Its unique properties allow for diverse chemical reactions, facilitating the creation of new materials with specific functions and applications across various industries.

Upstream product

• 1895006-01-5 dimesityl(trifluoromethyl)sulfonium trifluoromethanesulfonate 
• 182344-70-3 5-bromo-indole-1-carboxylic acid tert-butyl ester 
• 374818-66-3 tert-butyl 5-iodo-1H-indole-1-carboxylate 

Relevant academic research and scientific papers

A radical approach to the copper oxidative addition problem: Trifluoromethylation of bromoarenes

Transition metal–catalyzed arene functionalization has been widely used for molecular synthesis over the past century. In this arena, copper catalysis has long been considered a privileged platform due to the propensity of high-valent copper to undergo reductive elimination with a wide variety of coupling fragments. However, the sluggish nature of oxidative addition has limited copper’s capacity to broadly facilitate haloarene coupling protocols. Here, we demonstrate that this copper oxidative addition problem can be overcome with an aryl radical–capture mechanism, wherein the aryl radical is generated through a silyl radical halogen abstraction. This strategy was applied to a general trifluoromethylation of aryl bromides through dual copper-photoredox catalysis. Mechanistic studies support the formation of an open-shell aryl species.

FLUOROALKYLATION METHODS AND REAGENTS

A method of forming a fluorinated molecular entity includes reacting in a reaction mixture an aromatic halide, copper, a fluoroalkyl group, and a ligand. The aromatic halide includes an aromatic group and a halogen substituent bonded to the aromatic group. The ligand includes at least one group-V donor selected from phosphorus and an amine. The overall molar ratio of copper to aromatic halide in the reaction mixture is from 0.2 to 3. The method further includes forming a fluoroalkylarene including the aromatic group and the fluoroalkyl group bonded to the aromatic group. A composition, which may be used in the method, consists essentially of copper, the fluoroalkyl group, and the ligand, where the molar ratio of copper to the fluoroalkyl group is approximately 1.

A broadly applicable copper reagent for trifluoromethylations and perfluoroalkylations of aryl iodides and bromides

(Chemical Presented) Well compatible: The trifluoromethylations and perfluoroalkylations of aryl iodides and some aryl bromides with trifluoromethyl and perfluoroalkylcopper(I) phenanthroline complexes occur with broad scope at 25-50 8C (see scheme). The trifluoromethyl complex is prepared from inexpensive reagents and can be used in situ or isolated. The reactions tolerate a range of substituents and also occur with heteroaromatic systems.