76480-99-4

Usage

Uses

Used in Pharmaceutical Industry:
5-(TRIFLUOROMETHYL)-1H-PYRAZOL-3(2H)-ONE is used as a key intermediate in the synthesis of various Acyclic Pyrazole Sulfur Heterocyclic compounds. These compounds have potential applications as Uric Acid reabsorption inhibitors, which can be beneficial in the treatment of hyperuricemia and gout.
In the preparation of these heterocyclic compounds, 5-(TRIFLUOROMETHYL)-1H-PYRAZOL-3(2H)-ONE serves as a building block, providing a foundation for the development of new drugs with improved efficacy and selectivity. Its unique structure allows for further chemical modifications and functionalization, enabling the creation of a diverse range of therapeutic agents.
Additionally, the trifluoromethyl group in 5-(TRIFLUOROMETHYL)-1H-PYRAZOL-3(2H)-ONE may contribute to enhanced lipophilicity and metabolic stability, which can be advantageous for drug design and development. As a result, 5-(TRIFLUOROMETHYL)-1H-PYRAZOL-3(2H)-ONE holds significant potential in the pharmaceutical industry for the development of novel therapeutic agents targeting uric acid-related conditions.

Upstream product

• 372-31-6 ethyl 4,4,4-trifluoroacetoacetate 
• 106693-04-3 3,3,4,4,4-Pentafluoro-butyric acid ethyl ester 
• 144850-59-9 ethyl 3-bromo-3,4,4,4-tetrafluorobutanoate 
• 79424-03-6 ethyl 4,4,4-trifluoro-2-butynate 

Relevant academic research and scientific papers

Synthesis of 3-hydroxy-5-per(poly)fluoroalkyl pyrazoles

Treatment of ethyl α-per(poly)fluoroalkyl acetates 1 or ethyl α-iodo-β-per(poly)fluoroalkyl acrylates 2 with hydrazine gives 3-hydroxy-5-per(poly)fluoroalkyl pyrazoles 3 in excellent yield.The effect of halogens on the per(poly)fluoroalkyl chain and the reaction conditions were studied. - Keywords: Synthesis; Hydroxyper(poly)fluoroalkyl pyroles; NMR spectroscopy; IR spectroscopy; Mass spectrometry

A systematic exploration of nickel-pyrazolinato chemistry with alkali metals: New cages from serendipitous assembly

The preparation and properties of fourteen novel paramagnetic [NiIIx] aggregates bridged by pivalate, pyrazolinolate and in most cases hydroxide are reported. A rich structural diversity has been achieved by changing the nature of the alkali of the base used during the synthesis, leading to the nuclearities [NiII4NaI4] (2, 3, 4), [NiII5-NAI4] (5, 6, 7), [NiII5LiI6] (8), [NiII8MI2] (M = K (9, 10), Rb (11, 12), Cs (13, 14) and [NiII8] (15). All compounds have been characterised by single-crystal X-ray diffraction; however, full crystallographic details are given only for the representative molecules [Ni4Na4- (fpo)4(piv)8(Hpiv)8] (2), [Ni5Na4(OH)2- (mpo)4(piv)8(Hpiv)2(MeCN)2] (5), [Ni5Li6(OH)2 (fpo)2(piv)12(Hpiv)4] (8) [Ni8K2(OH)4(ppo) 4(piv)10(Hppo)2- (Hpiv)2(MeCN)2] (9), [Ni8Rb2(OH)4- (ppo)4(piv)10(Hppo) 2(Hpiv)2(MeCN)2] (11), [Ni8Cs2(OH)4(ppo) 4(piv)10(Hppo)2- (Hpiv)2(MeCN)2] (13) and [Ni8(OH)4-(mpo)2(PhCH 2CO2)10(Hmpo)8] (15). Variable-temperature bulk magnetisation measurements have been performed for each type of complex. The [NiII4NaI4] clusters show intramolecular antiferromagnetic coupling and a spin ground state of S = 0. Complexes of the type [NiII5NaI4] also display antiferromagnetic superexchange, leading to an S=1 spin ground state. The molecule with nuclearity [NiII5LiI6], in contrast, exhibits ferromagnetic interactions, resulting in the presence of low energy states with high multiplicity, and a spin ground state S>1. The [NiII5MI2] and [NiII8] clusters have the same topology of spin carriers, which display predominantly antiferromagnetic interactions to yield a diamagnetic ground state. The coupling within these octanuclear NiII clusters is rationalised in terms of the nature of the Ni-O-Ni angles within the core.

PYRAZOLE DERIVATIVE, INTERMEDIATE THEREFOR, PROCESSES FOR PRODUCING THESE, AND HERBICIDE CONTAINING THESE AS ACTIVE INGREDIENT

The present invention provides a pyrazole derivative of the general formula (1), which has an excellent efficacy as an active component for a herbicide, an intermediate for the production thereof, processes for the production thereof, and a herbicide cont

Synthesis and biological evaluation of novel pyrazoles and indazoles as activators of the nitric oxide receptor, soluble guanylate cyclase

Database searching and compound screening identified 1-benzyl-3-(3-dimethylaminopropyloxy)-indazole (benzydamine, 3) as a potent activator of the nitric oxide receptor, soluble guanylate cyclase. A comprehensive structure-activity relationship study surrounding 3 clearly showed that the indazole C-3 dimethylaminopropyloxy substituent was critical for enzyme activity. However replacement of the indazole ring of 3 by appropriately substituted pyrazoles maintained enzyme activity. Compounds were evaluated for inhibition of platelet aggregation and showed a general lipophilicity requirement. Aryl-substituted pyrazoles 32, 34, and 43 demonstrated potent activation of soluble guanylate cyclase and potent inhibition of platelet aggregation. Pharmacokinetic studies in rats showed that compound 32 exhibits modest oral bioavailability (12%) Furthermore 32 has an excellent selectivity profile notably showing no significant inhibition of phosphodiesterases or nitric oxide synthases.

Synthesis of Fluorinated Analogues of Geraniol

Syntheses of 3-(fluoromethyl)geraniol (4), 3-(difluoromethyl)geraniol (14), and 3-(trifluoromethyl)geraniol (20) are described.The key reaction in the routes to alcohols 4 and 20 which establishes the geranyl Z stereochemistry at the C(2)-C(3) double bond is the cis addition of (4-methylpent-3-en-1-yl)copper reagents to derivatives of ethyl 2-butynoate bearing appropriate functional groups at C(4).Attempts to prepare difluoromethyl alcohol 14 by similar routes were unsuccessful.However, the carbon skeleton of 14 was constructed by a Wittig condensation of 1,1-difluoro-6-methylhept-5-en-2-one (12) with triethyl phosphonoacetate in a reaction that yielded a 72:28 ratio of geranyl/neryl isomers.