123066-63-7

Basic information

• Product Name: 1-(4-NITROPHENYL)-3,5-DI(TRIFLUOROMETHYL)-1H-PYRAZOLE
• Synonyms: 1-(4-NITROPHENYL)-3,5-DI(TRIFLUOROMETHYL)-1H-PYRAZOLE;1-(4-Nitrophenyl)-3,5-bis(trifluoroMethyl)-1H-pyrazole
• CAS NO: 123066-63-7
• Molecular Formula: C₁₁H₅F₆N₃O₂
• Molecular Weight: 325.17
• Mol File: 123066-63-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(4-NITROPHENYL)-3,5-DI(TRIFLUOROMETHYL)-1H-PYRAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-NITROPHENYL)-3,5-DI(TRIFLUOROMETHYL)-1H-PYRAZOLE(123066-63-7)
• EPA Substance Registry System: 1-(4-NITROPHENYL)-3,5-DI(TRIFLUOROMETHYL)-1H-PYRAZOLE(123066-63-7)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 123066-63-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-(4-NITROPHENYL)-3,5-DI(TRIFLUOROMETHYL)-1H-PYRAZOLE is used as a chemical intermediate for the development of pharmaceutical compounds, leveraging its unique structure to enhance drug properties or create novel therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, 1-(4-NITROPHENYL)-3,5-DI(TRIFLUOROMETHYL)-1H-PYRAZOLE is utilized as a building block in the synthesis of agrochemicals, potentially contributing to the creation of new pesticides or other agricultural chemicals that can improve crop protection and yield.
Used in Organic Synthesis:
1-(4-NITROPHENYL)-3,5-DI(TRIFLUOROMETHYL)-1H-PYRAZOLE is used as a key component in organic synthesis processes, where its distinctive structure can be employed to construct a variety of complex organic molecules for different applications, including but not limited to, materials science and specialty chemicals.
Used in Biological Research:
1-(4-NITROPHENYL)-3,5-DI(TRIFLUOROMETHYL)-1H-PYRAZOLE is also used in biological research as a tool to study various biological activities, potentially aiding in the discovery of new mechanisms of action or the development of targeted therapies in medicine and agriculture.

Upstream product

• 636-99-7 4-nitrophenylhydrazine hydrochloride 
• 1522-22-1 1,1,1,5,5,5-hexafluoroacetylacetone 
• 1694-30-0 1,1,1,5,5,5-hexafluoro-4-hydroxy-pent-3-en-2-one 
• 100-16-3 4-nitrophenylhydrazone 

Downstream Products

• 1101891-14-8 N-(4-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)-2,3,3-trichloroacrylamide 
• 1315322-99-6 N-(4-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)-4-chlorobenzenesulfonamide 
• 1315323-00-2 N-(4-(3,5-bis(trifluoromethyl)-1H-pyrazole-1-yl)phenyl)-4-methylbenzenesulfonamide 
• 245747-08-4 N-(4-(3,5-bis(trifluoromethyl)-1H-pyrazole-1-yl)phenyl)-3-fluoroisonicotinamide 
• 245745-65-7 4'-[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl]isonicotinanilide monohydrochloride 
• 123066-64-8 4-[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl] aniline 

Relevant articles and documents

Formation and dehydration of a series of 5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazoles

Reaction of five (3-oxo-4,4,4-trifluorobutanoyl)heterocycles with hydrazine hydrate under mild conditions gave the corresponding 3-heterocyclyl-5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazoles. Thermal elimination of water from the 3-(thien-2-yl), 3-(pyridin-2-yl) and 3-(pyridin-4-yl) compounds readily gave the corresponding pyrazoles but acid catalysis was required to form 3-(benzothiazol-2-yl)-5-trifluoromethylpyrazole and 3-(1-methylbenzimidazol-2-yl)-5-trifluoromethylpyrazole. More forcing conditions were required for the analogous dehydration/aromatisations giving 3,5-bis(trifluoromethyl)-1-(4-nitrophenyl)pyrazole and 3,5-bis(trifluoromethyl)-1-pentafluorophenylpyrazole.

Pyrtriazoles, a Novel Class of Store-Operated Calcium Entry Modulators: Discovery, Biological Profiling, and in Vivo Proof-of-Concept Efficacy in Acute Pancreatitis

In recent years, channels that mediate store-operated calcium entry (SOCE, i.e., the ability of cells to sense a decrease in endoplasmic reticulum luminal calcium and induce calcium entry across the plasma membrane) have been associated with a number of d

MODULATORS OF SOCE, COMPOSITIONS, AND USES THEREOF

Compounds of Formula (I) able to modulate Store Operated Calcium Entry (SOCE). The disclosure also relates to the use of compounds of formula (I) for treatment of pathological conditions in which SOCE modulation might be beneficial, such as neglecting dis

Microwave-assisted and continuous flow multistep synthesis of 4-(pyrazol-1-yl)carboxanilides

A series of 4-(pyrazol-1-yl)carboxanilides active as inhibitors of canonical transient receptor potential channels were synthesized in an efficient three-step protocol using controlled microwave heating. The general synthetic strategy involves condensation of 4-nitrophenylhydrazine with appropriate 1,3-dicarbonyl building blocks, followed by reduction of the nitro group to the amine, which is then amidated with carboxylic acids. Compared to the conventional protocol a dramatic reduction in overall processing time from ～2 days to a few minutes was achieved, accompanied by significantly improved product yields. In addition, the first two steps in the synthetic pathway were also performed under continuous flow conditions providing similar isolated product yields. As an alternative to the three-step protocol, a novel two-step route to the desired 4-(pyrazol-1-yl)carboxanilides was devised involving condensation of 4-bromophenylhydrazine with appropriate 1,3-dicarbonyl building blocks, followed by Pd-catalyzed Buchwald-Hartwig amidation with carboxylic acid amides.

Synthesis of fluorinated heterocycles

Selected 1,3-diketones having a trifluoromethyl group and/or a fluorine in the 2-position were condensed with aromatic hydrazines, hydroxylamine, urea, thiourea, guanidine, and substituted anilines producing pyrazoles, isoxazoles, pyrimidines, and quinolines, respectively, in yields ranging from 27 to 87%.

3,5-Bis(trifluoromethyl)pyrazoles: A novel class of NFAT transcription factor regulator

A series of bis(trifiuoromethyl)pyrazoles (BTPs) has been found to be a novel inhibitor of cytokine production. Identified initially as inhibitors of IL-2 synthesis, the BTPs have been optimized in this regard and even inhibit IL-2 production with a 10-fold enhancement over cyclosporine in an ex vivo assay. Additionally, the BTPs show inhibition of IL-4, IL-5, IL-8, and eotaxin production. Unlike the IL-2 inhibitors, cyclosporine and FK506, the BTPs do not directly inhibit the dephosphorylation of NFAT by calcineurin.

3,5-BIS(TRIFLUOROMETHYL)PYRAZOLE AND SOME N-SUBSTITUTED DERIVATIVES

The pyrazoles (CF3)2C3HN2R (R = H, COPh, C6F5, C6H4NO2-4 and C6H3(NO2)2-2,4) have been prepared in yields ranging from 27percent (R = C6F5) to 78percent (R = C6H3(NO2)2-2,4) by the reaction between 1,1,1,5,5,5-hexafluoropentane-2,4-dione and the appropriately substituted hydrazine, NH2NHR.