26974-16-3

Usage

Uses

Used in Pharmaceutical Industry:
5-(2-Thienyl)-3-(Trifluoromethyl)-1H-Pyrazole is used as a compound with potential pharmacological activities for the development of new drugs. Its bioactive nature suggests that it may have applications in various therapeutic areas.
Used in Research Applications:
5-(2-Thienyl)-3-(Trifluoromethyl)-1H-Pyrazole is used as a research compound for studying its chemical properties and potential interactions with biological systems. The presence of a thiophene ring system, which is known for its electrically conducting properties, makes it an interesting subject for scientific investigation.
Used in Industrial Applications:
5-(2-Thienyl)-3-(Trifluoromethyl)-1H-Pyrazole is used in industrial settings where its unique chemical structure and properties may be leveraged for specific purposes. 5-(2-THIENYL)-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE's potential uses in various industries are still being explored and may include applications in materials science, chemical synthesis, or other areas.

InChI:InChI=1/C8H5F3N2S/c9-8(10,11)7-4-5(12-13-7)6-2-1-3-14-6/h1-4H,(H,12,13)

Upstream product

• 326-91-0 1,1,1-trifluoro-4-(2-thienyl)butane-2,4-dione 
• 98-03-3 thiophene-2-carbaldehyde 
• 1514-82-5 2-bromo-3,3,3-trifluoropropene 
• 4298-52-6 2-ethynyl-thiophene 
• 2236129-81-8 trifluoroacetaldehyde N-triftosylhydrazone 
• 371-67-5 2,2,2-trifluorodiazoethane 
• 950861-62-8 [Ag(thiophene-2-ethynide)]n 
• 88-15-3 2-Acetylthiophene 
• 128228-95-5 3-trifluoromethyl-5-(2-thienyl)-pyrazol-1-thiocarboxamide 

Downstream Products

• 182415-24-3 5-(thiophen-2-yl)-1H-pyrazole-3-carboxylic acid 
• 223499-62-5 5-(5-trifluoromethyl-2H-pyrazol-3-yl)-thiophene-2-carboxylic acid (4-chloro-phenyl)-amide 

Relevant academic research and scientific papers

Cycloaddition of Trifluoroacetaldehyde N-Triftosylhydrazone (TFHZ-Tfs) with Alkynes for Synthesizing 3-Trifluoromethylpyrazoles

A transition-metal-free [3 + 2] cycloaddition between trifluoroacetaldehyde N-triftosylhydrazone (TFHZ-Tfs) and alkynes is reported. This protocol provides an operationally simple and general method for the synthesis of diverse 3-trifluoromethylpyrazoles in good to excellent yields with broad substrate scope, including aryl, heteroaryl, and alkyl terminal alkynes, and electron-deficient internal alkynes. The synthetic potential of this method was further demonstrated by the synthesis of an antiarthritic drug Celecoxib in multigram scale.

Regioselective Synthesis of 3-Trifluoromethylpyrazole by Coupling of Aldehydes, Sulfonyl Hydrazides, and 2-Bromo-3,3,3-trifluoropropene

A general and practical strategy for 3-trifluoromethylpyrazole synthesis is reported that occurs by the three-component coupling of environmentally friendly and large-tonnage industrial feedstock 2-bromo-3,3,3-trifluoropropene (BTP), aldehydes, and sulfonyl hydrazides. This highly regioselective three-component reaction is metal-free, catalyst-free, and operationally simple and features mild conditions, a broad substrate scope, high yields, and valuable functional group tolerance. Remarkably, the reactions could be performed on a 100 mmol scale and smoothly afforded the key intermediates for the synthesis of celecoxib, mavacoxib, SC-560, and AS-136A. Preliminary mechanism studies indicated that a 1,3-hydrogen atom transfer process was involved in this transformation.

Pyrazole-3/5-carboxylic acids from 3/5-trifluoromethyl NH-pyrazoles

We report here the transformation of 3/5-trifluoromethylpyrazoles derivative into the corresponding NH-pyrazole-3/5-carboxylic acids. Moreover, from 4- or 5-iodinated-3/5-trifluoromethylpyrazoles building blocks and the use of Suzuki-Miyaura or Negishi reactions followed by the trifluoromethyl hydrolysis, we illustrate short and original accesses to many series of NH-pyrazole-3/5-carboxylic acids otherwise difficult to prepare.

Silver-mediated cycloaddition of alkynes with CF3CHN 2: Highly regioselective synthesis of 3-trifluoromethylpyrazoles

Silver screen: The title reaction provides a convenient and efficient method for the construction of 5-substituted 3-trifluoromethylpyrazoles under mild reaction conditions. By using this protocol, the marketed drug Celecoxib (antiarthritic) could be easily synthesized (see scheme; DMF=N,N- dimethylformamide). Copyright

Novel potent and selective calcium-release-activated calcium (CRAC) channel inhibitors. Part 2: Synthesis and inhibitory activity of aryl-3-trifluoromethylpyrazoles

To identify potent and selective calcium-release-activated calcium (CRAC) channel inhibitors, we examined the structure-activity relationships of the pyrazole and thiophene moieties in compound 4. Compound 25b was found to exhibit highly potent and selective inhibitory activity for CRAC channels and further modifications of the pyrazole and benzoyl moieties of compound 25b produced compound 29. These compounds were potent inhibitors of IL-2 production in vitro and also acted as inhibitors in pharmacological models of diseases resulting from T-lymphocyte activation, after oral administration.