217959-45-0

Basic information

• Product Name: 5-TRIFLUOROMETHYLTHIOPHENE-3-ONE
• Synonyms: 5-TRIFLUOROMETHYLTHIOPHENE-3-ONE;5-(trifluoroMethyl)thiophen-3-ol;5-TRIFLUOROTHIOPHENE-3-ONE;Thiophene-3-ol,5-(trifluoroMethyl)-;5-Trifluoromethyl-3-hydroxythiophene
• CAS NO: 217959-45-0
• Molecular Formula: C₅H₃F₃OS
• Molecular Weight: 168.14
• EINECS: 200-258-5
• Mol File: 217959-45-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 74-78°C/12mm
• Flash Point: 42.1 °C
• Appearance: /
• Density: 1.541 g/cm³
• Storage Temp.: 2-8°C(protect from light)
• PKA: 8.68±0.10(Predicted)
• CAS DataBase Reference: 5-TRIFLUOROMETHYLTHIOPHENE-3-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-TRIFLUOROMETHYLTHIOPHENE-3-ONE(217959-45-0)
• EPA Substance Registry System: 5-TRIFLUOROMETHYLTHIOPHENE-3-ONE(217959-45-0)

Safety Data

• Hazardous Substances Data: 217959-45-0(Hazardous Substances Data)

Usage

General Description

5-Trifluoromethylthiophene-3-one is a chemical compound with the molecular formula C5H3F3OS. It is a pale yellow liquid with a pungent odor, and it is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. 5-TRIFLUOROMETHYLTHIOPHENE-3-ONE is known for its strong electrophilic nature due to the presence of the ketone functional group, making it a versatile building block in organic synthesis. It is also known for its unique electronic properties, which make it useful in the development of organic electronic materials. Additionally, its trifluoromethyl group enhances its lipophilicity, making it suitable for use in drug design. Overall, 5-Trifluoromethylthiophene-3-one is an important chemical building block with various industrial applications.

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 articles and documents

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.

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.

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.