85068-33-3

Usage

Uses

Used in Pharmaceutical Industry:
3,5-Bis(trifluoromethyl)phenylacetic acid is used as a building block for synthesizing pentaamine and bis-heterocyclic libraries. Its structural features contribute to the development of novel compounds with potential therapeutic applications, enhancing drug discovery and innovation in the pharmaceutical sector.
Used in Environmental Analysis:
3,5-Bis(trifluoromethyl)phenylacetic acid serves as a reagent in the determination of ionic perfluorinated substances and telomers in leachates from landfills and sediment samples. Its role in environmental analysis aids in monitoring and assessing the presence of these potentially harmful substances, contributing to environmental protection and management efforts.

InChI:InChI=1/C10H6F6O2/c11-9(12,13)6-1-5(3-8(17)18)2-7(4-6)10(14,15)16/h1-2,4H,3H2,(H,17,18)/p-1

Upstream product

• 328-70-1 3,6-bis(trifluoromethyl)bromobenzene 
• 88444-81-9 3,5-bis(trifluoromethyl)phenylacetylene 
• 124-38-9 carbon dioxide 
• 328-73-4 3,5-bis(trifluoromethyl)iodobenzene 
• 64-19-7 acetic acid 
• 108-59-8 malonic acid dimethyl ester 
• 95299-16-4 methyl [3,5-bis(trifluoromethyl)-phenyl]-acetate 
• 785-56-8 3,5-bis(trifluoromethyl)phenyl carboxylic acid chloride 
• 725-89-3 3,5-bistrifluoromethylbenzoic acid 
• 32247-96-4 3,5-bis(trifluoromethyl)benzyl bromide 
• 85068-32-2 3,5-bis(trifluoromethyl)phenylacetonitrile 

Downstream Products

• 374791-09-0 N-(4-Oxo-1-phenylcyclohexyl)-3,5-bis(trifluoromethyl)benzeneacetamide 
• 95299-16-4 methyl [3,5-bis(trifluoromethyl)-phenyl]-acetate 
• 178165-94-1 N-[2-(3,4-Dichlorophenyl)-2-(4-hydroxy-4-phenylpiperidino)ethyl]-N-methyl-3,5-bis(trifluoromethyl)phenylacetamide hydrochloride salt 
• 299428-12-9 (2R)-2-[4-{[3,5-bis(trifluoromethyl)phenyl]acetyl}-2-(3,4-dichlorophenyl)morpholin-2-yl]ethanol 
• 863456-25-1 (2R)-2-[4-{[3,5-bis(trifluoromethyl)phenyl]acetyl}-2-(3,4-dichlorophenyl)morpholin-2-yl]ethanol 
• 407637-68-7 2-[3,5-Bis(trifluoromethyl)phenyl]-N-{[4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}acetamide 
• 1161361-85-8 2-(3,5-bis(trifluoromethyl)phenyl)-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)acetamide 
• 868167-62-8 2-[3,5-bis(trifluoromethyl)phenyl]-N-{[5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}acetamide 
• 927672-06-8 2-(3,5-bis-trifluoromethyl-phenyl)-N-[2-(2,6-dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-ylmethyl]-acetamide 
• 1450833-02-9 2-(3,5-bis(trifluoromethyl)phenyl)-N-(4-((2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl)butyl)acetamide 
• 289686-70-0 α,α-Dimethyl-3,5-bis(trifluoromethyl)benzeneacetic Acid 

Relevant academic research and scientific papers

Visible-Light-Enabled Carboxylation of Benzyl Alcohol Derivatives with CO2 Using a Palladium/Iridium Dual Catalyst

A highly efficient carboxylation of benzyl alcohol derivatives with CO2 using a palladium/iridium dual catalyst under visible-light irradiation was developed. A wide range of benzyl alcohol derivatives could be employed to provide benzylic carboxylic acids in moderate to high yields. Mechanistic studies indicated that the oxidative addition of benzyl alcohol derivatives was possibly the rate-determining-step. It was also found that a switchable site-selective carboxylation between benzylic C?O and aryl C?Cl moieties could be achieved simply by changing the palladium catalyst.

Development of Novel Mitochondrial Pyruvate Carrier Inhibitors to Treat Hair Loss

Herein, we report the synthesis and evaluation of novel analogues of UK-5099 both in vitro and in vivo for the development of mitochondrial pyruvate carrier (MPC) inhibitors to treat hair loss. A comprehensive understanding of the structure-activity relationship was obtained by varying four positions of the hit compound, namely, the alkyl group on the N1 position, substituents on the indole core, various aromatic and heteroaromatic core structures, and various Michael acceptors. The major discovery was that the inhibitors with a 3,5-bis(trifluoromethyl)benzyl group at the N1 position were shown to have much better activity than JXL001 (UK-5099) to increase cellular lactate production. Additionally, analogue JXL069, possessing a 7-azaindole heterocycle, was also shown to have significant MPC inhibition activity, which further increases the chemical space for drug design. Finally, more than 10 analogues were tested on shaved mice by topical treatment and promoted obvious hair growth on mice.

Oxidation of Alkynyl Boronates to Carboxylic Acids, Esters, and Amides

A general efficient protocol was developed for the synthesis of carboxylic acids, esters, and amides through oxidation of alkynyl boronates, generated directly from terminal alkynes. This protocol represents the first example of C(sp)?B bond oxidation. This approach displays a broad substrate scope, including aryl and alkyl alkynes, and exhibits excellent functional group tolerance. Water, primary and secondary alcohols, and amines are suitable nucleophiles for this transformation. Notably, amino acids and peptides can be used as nucleophiles, providing an efficient method for the synthesis and modification of peptides. The practicability of this methodology was further highlighted by the preparation of pharmaceutical molecules.

COMPOSITIONS AND METHODS FOR MODULATING HAIR GROWTH

The present disclosure relates to compounds that are capable of inhibiting the mitochondrial pyruvate carrier and promoting hair growth. The disclosure further relates to methods of promoting hair growth or treating conditions or disorders affecting hair growth, such as baldness or alopecia.

COMPOSITIONS AND METHODS FOR MODULATING HAIR GROWTH

The present disclosure relates to compounds that are capable of inhibiting the mitochondrial pyruvate carrier and promoting hair growth. The disclosure further relates to methods of promoting hair growth or treating conditions or disorders affecting hair growth, such as baldness or alopecia.

A intermediate [...] 2 - (3,5-bis-trifluoromethyl-phenyl) - 2-methyl-propionic acid synthetic method (by machine translation)

The invention discloses a intermediate [...] 2 - (3,5-bis-trifluoromethyl-phenyl) - 2-methyl-propionic acid synthetic method, comprising the following steps: in order to compound 3.5-bis (trifluoromethyl) bromobenzene as raw materials, the presence of the alkali reagent 1st the 1st diethyl malonate in a solvent in the reaction, a generating compound, then the compound in the solvent 2nd, through the 2nd alkali reagent to carry out saponification, decarboxylation reaction, and the second generating compound, the final compound II in the presence of the alkali reagent 3rd the 3rd with methylation reagent in the reaction in the solvent to obtain 2 - (3,5-bis-trifluoromethyl-phenyl) - 2-methyl-propionic acid. The invention uses the one-pot synthesis preparation [...] intermediate, not only the easily obtained raw material used, the cost is low, and the reaction flow is short, the operation is simple, the production cost is low, is convenient for industrial production and application. (by machine translation)

Synthesis method of netupitant intermediates

The invention discloses a synthesis method of netupitant intermediates. The method includes the steps of dissolving cyano-acetate and 3,5-bis(trifluoromethylphenyl halide) in solvent, conducting decarboxylation and cyanomethylation reaction under the effect of a palladium catalyst and organophosphorus ligand to obtain 2-(3,5-bistrifluoromethylphenyl)acetonitrile, converting a cyano group into a carboxy group through alkali to obtain 2-(3,5-bistrifluoromethylphenyl)acetic acid, and making 2-(3,5-bistrifluoromethylphenyl)acetic acid react with a methylating agent to obtain a target product. The method is easy to operate, free of side reaction and high in yield, and raw materials are low in price, easy to obtain and easy to synthesize.

Palladium-catalyzed silver-mediated α-arylation of acetic acid: A new approach for the α-arylation of carbonyl compounds

A new approach for the α-arylation of acetic acid through Pd-catalyzed silver-mediated direct C-H arylation of acetic acid with aryl iodides was developed. This protocol provided a straightforward method for the synthesis of a diverse set of α-phenylacetic acids. Palladium served on a silver platter: A new approach for the α-arylation of acetic acid through Pd-catalyzed silver-mediated direct C-H arylation of acetic acid with aryl iodides is presented. This protocol provides a straightforward method for the synthesis of a diverse set of α-phenylacetic acids. Deuteration experiments are performed to help elucidate the reaction mechanism.

Process for preparing [bis-(trifluoromethyl)-phenyl]-acetic acids and alkyl esters thereof and dialkyl [bis-(trifluoromethyl)-phenyl]-malonates

[Bis-(trifluoromethyl)-phenyl]-acetic acids are obtained in an advantageous manner by reacting an appropriate bromo- or iodo-bis-(trifluoromethyl)-benzene with a di-C1-C4-alkyl malonate in the presence of a deprotonating agent and a copper salt and hydrolysing and decarboxylating the reaction product in basic medium. It is possible to obtain a mixture of alkyl [bis-(trifluoromethyl)-phenyl]-acetate and alkyl [bis-(tri-fluoromethyl)-phenyl]-malonate by admixing the reaction mixture which is present before hydrolysis and complete decarboxylation with water and acid and heating. From the mixture, it is possible to obtain alkyl [bis-(trifluoromethyl)-phenyl]-acetate by distillation under reduced pressure and dialkyl [bis-(trifluoromethyl)-phenyl]-malonate by work-up by column chromatography, fractional distillation or film distillation. [Bis-(trifluoromethyl)-phenyl]-malonic esters are novel compounds.

Quinolones as gonadotropin releasing hormone (GnRH) antagonists: Simultaneous optimization of the C(3)-aryl and C(6)-substituents

A series of 3-arylquinolones was prepared and evaluated for their ability to act as gonadotropin releasing hormone (GnRH) antagonists. A variety of substitution patterns of the 3-aryl substituent are described. The 3,4,5-trimethylphenyl substituent (23h) was found to be optimal. (C) 2000 Elsevier Science Ltd. All rights reserved.