217959-45-0

Usage

Uses

Used in Pharmaceutical Industry:
5-Trifluoromethylthiophene-3-one is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its electrophilic nature and unique electronic properties make it a valuable component in the development of new drugs, particularly those targeting specific biological pathways or requiring enhanced lipophilicity for improved drug delivery and efficacy.
Used in Agrochemical Industry:
In the agrochemical sector, 5-Trifluoromethylthiophene-3-one serves as an intermediate in the synthesis of agrochemicals. Its properties allow for the creation of compounds with specific pesticidal or herbicidal activities, contributing to the development of more effective and targeted crop protection agents.
Used in Organic Synthesis:
5-Trifluoromethylthiophene-3-one is utilized as a versatile building block in organic synthesis. Its strong electrophilic nature and the presence of the trifluoromethyl group make it suitable for the creation of a wide range of organic compounds, including those with potential applications in materials science, specialty chemicals, and other industrial areas.
Used in Organic Electronic Materials:
The unique electronic properties of 5-Trifluoromethylthiophene-3-one make it useful in the development of organic electronic materials. It can be incorporated into the design of organic semiconductors, which have applications in various electronic devices such as organic light-emitting diodes (OLEDs), organic photovoltaics (OPVs), and organic field-effect transistors (OFETs).
Used in Drug Design:
Due to its enhanced lipophilicity, 5-Trifluoromethylthiophene-3-one is used in drug design to improve the pharmacokinetic properties of new drug candidates. This can lead to better absorption, distribution, metabolism, and excretion (ADME) profiles, which are crucial for the success of a drug in clinical trials and eventual market approval.

Synthetic route

3-Hydroxy-5-trifluoromethyl-2-thiophenecarboxylic Acid → 4-Hydroxy-2-(trifluoromethyl)thiophene (217959-45-0)

Conditions	Yield
at 100℃; for 3.5h; Decarboxylation;	82%
	82%

methyl 3-hydroxy-5-(trifluoromethyl)thiophene-2-carboxylate (157162-16-8) → 4-Hydroxy-2-(trifluoromethyl)thiophene (217959-45-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 65 percent / aq. NaOH / 3 h / Heating 2: 82 percent / 3.5 h / 100 °C View Scheme

trifluoromethylsulfonic anhydride (358-23-6) + 4-Hydroxy-2-(trifluoromethyl)thiophene (217959-45-0) → 4-trifluoromethanesulfonate-2-trifluoromethylthiophene (827322-77-0)

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; for 3h;	92%

N-{[5-methyl-4-(methylsulfonyl)pyrimidin-2-yl]methyl}cyclopropane-carboxamide (1140520-39-3) + 4-Hydroxy-2-(trifluoromethyl)thiophene (217959-45-0) → N-[(5-methyl-4-{[5-(trifluoromethyl)-3-thienyl]oxy}pyrimidin-2-yl)methyl]cyclopropanecarboxamide

Conditions	Yield
With potassium carbonate In acetonitrile for 8h; Heating / reflux;	18%

2,6-difluoro pyridine (1513-65-1) + 4-Hydroxy-2-(trifluoromethyl)thiophene (217959-45-0) → 2-fluoro-6-(2-trifluoromethyl-4-thienyloxy)pyridine (653601-80-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20 - 80℃; for 4h;

Upstream product

• 157162-16-8 methyl 3-hydroxy-5-(trifluoromethyl)thiophene-2-carboxylate 
• 217959-85-8 3-Hydroxy-5-trifluoromethyl-2-thiophenecarboxylic Acid 

Relevant academic research and scientific papers

Herbicidal pyridine compounds

The novel compounds of formula I: wherein R, A, X1, X2, X3, Z and m have the meaning given in claim 1, and the agronomically acceptable salts or N-oxides thereof, and herbicidal compositions containing such compounds as active ingredients.

Preparation of 4-hydroxy-2-trifluoromethylthiophene: A novel bioisostere of α,α,α-trifluoro-m-cresol

A simple and convenient four-step synthesis of 4-hydroxy-2- trifluoromethylthiophene (1) a novel bioisostere of α,α,α- trifluoro-m-cresol is reported. The key step is the condensation between ethyl 3-methoxy-4,4,4-trifluorocrotonate and methyl thioglycolate to form methyl 3-hydroxy-5- trifluoromethylthiophene-2-carboxylate (6). Hydrolysis of the ester followed by decarboxylation furnishes 1. Multi-hundred gram quantities of 1 have been obtained utilizing the present procedure.

Thienyloxypyridines and-pyrimidines useful as herbicidal agents

The present invention provides a herbicidal compound of formula I, methods for the preparation thereof and intermediates useful therefor. wherein X and Y are each independently O or S; Z is N or CR4.

Herbicidal 2-(cycloalk(en)yloxy)-6-(hetero)aryloxy(thio)pyridines

The novel compounds of formula I: wherein R, A, X1, X2, X3and Z have the meaning given in claim 1, and the agronomically acceptable salts or N-oxide thereof, and herbicidal compositions containing such compounds as active ingredients.

Herbicidal pyridine compounds

The novel compounds of formula I: wherein one of the groups X1, X2and X3represents N or CR1and the others represent CR1; R1each independently represents a hydrogen or halogen atom or an optionally substituted alkyl, alkenyl, alkinyl, alkoxy, alkoxyalkyl, alkoxyalkoxy group or a haloalkyl, haloalkoxy, cyano, nitro or SF5group, or -S(O)p-R10in which p is 0, 1 or 2 and R10represents an alkyl or haloalkyl group, or -NR2R3in which R2and R3each independently represent a hydrogen atom, an alkyl, alkenyl, aralkyl or aryl group, or R4-O-C(Y)- in which R4represents an alkyl group and Y represents O or S; A represents an optionally substituted aryl group, an optionally substituted 5- or 6- membered nitrogen-containing heteroaromatic group or an optionally substituted thienyl group; R represents an optionally substituted haloalkyl or haloalkenyl group; m is 0, 1, 2 or 3; Z represents an oxygen or sulfur atom; and the agronomically acceptable salts or N-oxides thereof; with the proviso that R represents an optionally substituted haloalkenyl group when m is 0. and herbicidal compositions containing such compounds as active ingredients.

Herbicidal thienyloxyazines

A compound is disclosed having the formula: STR1 The compound is useful as an active ingredient in a herbicidal composition.