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Chen, Changle’s team published research in Organometallics in 2010 | CAS: 20154-03-4

3-(Trifluoromethyl)-1H-pyrazole(cas: 20154-03-4) belongs to pyrazoles. Pyrazole derivatives have been reported to exhibit a wide range of applications in medicinal chemistry and pharmacology. A large number of drugs incorporating pyrazole structure have been utilized as partial agonists for nicotinic acid receptors, antidepressants, antimicrobial agents, antiviral agents, and antifungal agents solely or along with the combination of other structural motifs.HPLC of Formula: 20154-03-4

HPLC of Formula: 20154-03-4In 2010 ,《Lewis Acid Catalyzed Synthesis of Poly(pyrazolyl)borate Ligands》 appeared in Organometallics. The author of the article were Chen, Changle; Jordan, Richard F.. The article conveys some information:

Lewis acids catalyze the reaction of Li[MeBH3] and Na[BH4] with pyrazoles to yield poly(pyrazolyl)borates under mild conditions. The reaction of Li[MeBH3] with 2 equiv of 3-mesitylpyrazole (HpzMs) at 23° (2 days) affords Li[MeB(3-mesityl-pz)2H] (Li[MeBpMs]) and Li[MeB(3-mesityl-pz)(5-mesityl-pz)H] (Li[MeBpMs*]) in 88% yield (3:1 isomer ratio) in the presence of MeB(OiPr)2 (5 mol % vs. HpzMs) but only 28% yield without this additive. Similar enhancements in the yield of Li[MeBpR] products are observed in the reaction of Li[MeBH3] with 3-tBu-pyrazole, 3,5-Me2-pyrazole (Hpz*), and 3,5-tBu2-pyrazole. The kinetics of the MeB(OiPr)2-catalyzed and uncatalyzed reaction of Li[MeB(3-mesityl-pz)H2]/Li[MeB(5-mesityl-pz)H2] with HpzMs were compared assuming that Li[MeB(3-mesityl-pz)H2] and Li[MeB(5-mesityl-pz)H2] react at the same rate. The estimated second-order rate constants are k(catalyzed) = 1.0 × 10-4 M-1 s-1 and k(uncatalyzed) = 2.1 × 10-5 M-1 s-1 at 23° in THF. The reaction of Li[MeBH3] with 3 equiv of HpzMs (THF, 60°, 2 days) in the presence of 3 mol % MeB(OiPr)2 affords Li[MeB(3-mesityl-pz)3] (75% yield), but only Li[MeBpMs] and Li[MeBpMs*] without this additive. Similar results were observed for the reaction of Li[MeBH3] with 3-CF3-pyrazole. The reaction of Na[BH4] and 3 equiv of Hpz* (THF, 60°, 4 h) gave Na[B(3,5-Me2-pz)2H2] in 93% yield in the presence of BF3·Et2O (5 mol % vs. Hpz*) but only 5% without this additive. Coordination of the pyrazole to the Lewis acid is expected to decrease the pKa of the pyrazole and increase the rate of B-H bond protonolysis. After reading the article, we found that the author used 3-(Trifluoromethyl)-1H-pyrazole(cas: 20154-03-4HPLC of Formula: 20154-03-4)

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Rampazzi, Vincent’s team published research in ChemCatChem in 2012 | CAS: 20154-03-4

3-(Trifluoromethyl)-1H-pyrazole(cas: 20154-03-4) belongs to pyrazoles. The application of pyrazole derivatives in the development of anticancer agents has been thoroughly investigated and verified. Moreover, the medicinal features of a number of natural products incorporating pyrazole moiety such as pyrazofurin, pyrazofurin B, pyrazole-3(5)-carboxylic acid and 4-methylpyrazole-3(5)-carboxylic acid have been reported.Related Products of 20154-03-4

In 2012,Rampazzi, Vincent; Massard, Alexandre; Richard, Philippe; Picquet, Michel; Le Gendre, Pierre; Hierso, Jean-Cyrille published 《A simple phosphine-diolefin-promoted copper-catalyzed N-arylation of pyrazoles with (hetero)aromatic bromides: the case of chloroarenes revisited》.ChemCatChem published the findings.Related Products of 20154-03-4 The information in the text is summarized as follows:

A molecularly defined new phosphine-diolefin cubane copper pre-catalyst used at 1.25 mol % under mild conditions promotes the coupling of pyrazoles to functionalized aryl and heteroaryl bromides, which hold a variety of functional groups. This versatile phosphorus-based system was thus successfully used, under identical conditions, for the coupling of a large scope of heteroaromatics to selectively produce pyridinyl- and pyrimidinyl-pyrazoles, as well as several novel furyl-, thienyl- and thiazolyl-substituted pyrazoles. The careful investigation of coupling with the analogous aryl and heteroaryl chlorides clearly indicated that for specifically activated chloroarenes a direct nucleophilic aromatic substitution (SNAr) is easily achieved in the absence of any copper and ligand. These results are pertinent with regards to the reported protocols in which copper-ligand systems have been claimed as useful for coupling activated chloroarenes. In the experiment, the researchers used many compounds, for example, 3-(Trifluoromethyl)-1H-pyrazole(cas: 20154-03-4Related Products of 20154-03-4)

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Guillou, Sandrine’s team published research in Tetrahedron in 2011 | CAS: 20154-03-4

In 2011,Guillou, Sandrine; Bonhomme, Frederic J.; Ermolenko, Mikhail S.; Janin, Yves L. published 《Simple preparations of 4 and 5-iodinated pyrazoles as useful building blocks》.Tetrahedron published the findings.Computed Properties of C4H3F3N2 The information in the text is summarized as follows:

The pyrazole nucleus has recently become a recurrent scaffold in the research fields of CropScience and oncol. We report here the preparation of an array of 4- and 5-iodinated pyrazole derivatives, such as 4-iodo-3-trifluoromethylpyrazole or Et 5-iodo-4-carboxy-3-trifluoromethylpyrazoles. This work provide access to many new pyrazole derivative, including eleven original out of sixteen iodinated building blocks, thus opening accesses to new chem. entities featuring a pyrazole nucleus.3-(Trifluoromethyl)-1H-pyrazole(cas: 20154-03-4Computed Properties of C4H3F3N2) was used in this study.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Sakamoto, Ryu’s team published research in Organic Letters in 2017 | CAS: 5952-93-2

Methyl 1-methyl-1H-pyrazole-4-carboxylate(cas: 5952-93-2) belongs to pyrazoles. Pyrazoles and their related multiring analogs are common elements of a wide variety of bioactive compounds. These ring structures are rare in nature. A consequence of this is that they have previously been thought to be poor moieties to include in potential new drugs. Safety of Methyl 1-methyl-1H-pyrazole-4-carboxylate

Safety of Methyl 1-methyl-1H-pyrazole-4-carboxylateOn October 6, 2017 ,《The Direct C-H Difluoromethylation of Heteroarenes Based on the Photolysis of Hypervalent Iodine(III) Reagents That Contain Difluoroacetoxy Ligands》 was published in Organic Letters. The article was written by Sakamoto, Ryu; Kashiwagi, Hirotaka; Maruoka, Keiji. The article contains the following contents:

In this letter, an efficient method for the photolytic generation of difluoromethyl radicals from [bis(difluoroacetoxy)iodo]benzene reagents is described. The present approach enables the introduction of difluoromethyl groups into various heteroarenes under mild conditions in the absence of any addnl. reagents or catalysts. The experimental process involved the reaction of Methyl 1-methyl-1H-pyrazole-4-carboxylate(cas: 5952-93-2Safety of Methyl 1-methyl-1H-pyrazole-4-carboxylate)

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Kim, Og Soon’s team published research in Organic Letters in 2017 | CAS: 52096-24-9

1-Butyl-1H-pyrazole(cas: 52096-24-9) belongs to pyrazoles. Pyrazoles and their related multiring analogs are common elements of a wide variety of bioactive compounds. These ring structures are rare in nature. A consequence of this is that they have previously been thought to be poor moieties to include in potential new drugs. Product Details of 52096-24-9

Product Details of 52096-24-9On March 17, 2017, Kim, Og Soon; Jang, Jin Hyeok; Kim, Hyun Tae; Han, Su Jin; Tsui, Gavin Chit; Joo, Jung Min published an article in Organic Letters. The article was 《Synthesis of Fluorescent Indazoles by Palladium-Catalyzed Benzannulation of Pyrazoles with Alkynes》. The article mentions the following:

Pentasubstituted indazoles such as I (R = H, Me, t-Bu, MeO, EtO2C, F, Cl) were prepared in 34-84% yields by oxidative benzannulation reactions of pyrazoles such as 1-methylpyrazole with sym. internal alkynes such as 4-(4-RC6H4CC)C6H4R (R = H, Me, t-Bu, MeO, EtO2C, F, Cl) in the presence of Pd(OAc)2 and Cu(OAc)2 in 1,4-dioxane or by benzannulation of substituted 4-bromopyrazoles with sym. internal alkynes in the presence of Pd(OAc)2, t-Bu3P•HBF4, K2CO3, and pivalic acid in toluene; unsym. internal alkynes gave mixtures of regioisomers. 1,2-Disubstituted imidazoles also underwent oxidative benzannulation with diphenylacetylene in the presence of Pd(OAc)2 and Cu(OAc)2 in 1,4-dioxane to yield tetraphenylbenzimidazoles in 41-50% yields. The fluorescence and optical bandgaps of I (R = H, t-Bu, MeO, EtO2C, F, Cl) were determined The structure of I (R = H) was determined by X-ray crystallog. In the part of experimental materials, we found many familiar compounds, such as 1-Butyl-1H-pyrazole(cas: 52096-24-9Product Details of 52096-24-9)

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Schmalzbauer, Matthias’s team published research in Chem in 2020 | CAS: 474432-62-7

Pyrazolo[1,5-a]pyridine-7-carboxylic acid(cas: 474432-62-7) belongs to pyrazoles. Pyrazoles are commonly used scaffold molecules in drug discovery projects. The use of pyrazole derivatives is based on their analgesic, monoamine oxidase inhibitory, anti-inflammatory, antipyretic, neuroleptic, anticonvulsant, antiarrhythmic, sedative, muscle relaxant, antidiabetic and antibacterial activities. Recommanded Product: 474432-62-7

Recommanded Product: 474432-62-7On October 8, 2020 ,《Redox-Neutral Photocatalytic C-H Carboxylation of Arenes and Styrenes with CO2》 was published in Chem. The article was written by Schmalzbauer, Matthias; Svejstrup, Thomas D.; Fricke, Florian; Brandt, Peter; Johansson, Magnus J.; Bergonzini, Giulia; Koenig, Burkhard. The article contains the following contents:

A redox-neutral CH carboxylation of arenes and styrenes using a photocatalytic approach was described for the synthesis of aryl/unsaturated-carboxylic acids RCOOH [R = 1-naphthyl, CH=CHPh, 5-cyano-2-thienyl, etc.]. Upon blue-light excitation, the anthrolate anion photocatalyst was able to reduce many aromatic compounds to their corresponding radical anions, which react with CO2 to afford carboxylic acids. High-throughput screening and computational anal. suggest that a correct balance between electron affinity and nucleophilicity of substrates was essential. This novel methodol. enabled the carboxylation of numerous aromatic compounds, including many that were not tolerated in classical carboxylation chem. Over 50 examples of CH functionalizations using CO2 or ketones illustrated a broad applicability. The experimental process involved the reaction of Pyrazolo[1,5-a]pyridine-7-carboxylic acid(cas: 474432-62-7Recommanded Product: 474432-62-7)

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Diamanti, Eleonora’s team published research in Synthesis in 2016 | CAS: 20154-03-4

In 2016,Diamanti, Eleonora; Bottegoni, Giovanni; Goldoni, Luca; Realini, Natalia; Pagliuca, Chiara; Bertozzi, Fabio; Piomelli, Daniele; Pizzirani, Daniela published 《Pyrazole-Based Acid Ceramidase Inhibitors: Design, Synthesis, and Structure-Activity Relationships》.Synthesis published the findings.Related Products of 20154-03-4 The information in the text is summarized as follows:

Acid ceramidase (a.c.) is a lysosomal cysteine amidase responsible for the cleavage of ceramide into sphingosine, which is then phosphorylated to sphingosine 1-phosphate. AC regulates the intracellular levels of ceramide and sphingosine, and a.c. inhibition may be useful in the treatment of disorders, such as cancer, in which ceramide-mediated signaling may be dysfunctional. Despite their potential exptl. and therapeutic value, the number of available small-mol. inhibitors of a.c. activity remains limited. In the present study is described the discovery of a class of potent pyrazole carboxamide-based a.c. inhibitors, which were identified using the at. property field (APF) approach and developed through systematic SAR studies and in vitro pharmacol. characterization. The best compound of this series inhibits a.c. with nanomolar potency and causes ceramide accumulation and sphingosine depletion in intact G361 proliferative melanoma cells. By expanding the current armamentarium of a.c. inhibitors, these results should facilitate future efforts to unravel the biol. of a.c. and the therapeutic potential of its inhibition.3-(Trifluoromethyl)-1H-pyrazole(cas: 20154-03-4Related Products of 20154-03-4) was used in this study.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Li, Song’s team published research in Wuji Huaxue Xuebao in 2018 | CAS: 29004-73-7

(3-methyl-1H-pyrazol-5-yl)methanol(cas: 29004-73-7) belongs to pyrazoles. Pyrazoles and their related multiring analogs are common elements of a wide variety of bioactive compounds. These ring structures are rare in nature. A consequence of this is that they have previously been thought to be poor moieties to include in potential new drugs. Quality Control of (3-methyl-1H-pyrazol-5-yl)methanol

In 2018,Wuji Huaxue Xuebao included an article by Li, Song; Gan, Xian-xue; Tang, Liang-fu. Quality Control of (3-methyl-1H-pyrazol-5-yl)methanol. The article was titled 《Syntheses and catalytic properties of metal carbonyl derivatives with hydroxymethyl functionalized pyrazoles》. The information in the text is summarized as follows:

Reaction of tungsten or molybdenum carbonyl with 3(5)-hydroxymethyl-5(3)-methylpyrazole (L1), 4-hydroxymethylpyrazole (L2) and bis(3-hydroxymethyl-5-methylpyrazol-1-yl)methane (L3) yielded complexes LW(CO)5 (L = L1 or L2) and L3M(CO)4 (M = Mo or W), resp. These complexes have been fully characterized by NMR, IR and x-ray crystal structural analyses, indicating that they form 1D or 2D organometallic supramol. architectures through O-H···O, N-H···O and O-H···OC-M hydrogen bonding interactions, and these structures are significantly affected by the relative position of the hydroxymethyl group on the pyrazole ring. In addition, these complexes show moderate catalytic activity for the cyclotrimerization reaction of phenylacetylene. The experimental part of the paper was very detailed, including the reaction process of (3-methyl-1H-pyrazol-5-yl)methanol(cas: 29004-73-7Quality Control of (3-methyl-1H-pyrazol-5-yl)methanol)

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Ehmke, Veronika’s team published research in ChemMedChem in 2013 | CAS: 20154-03-4

《Optimization of Triazine Nitriles as Rhodesain Inhibitors: Structure-Activity Relationships, Bioisosteric Imidazopyridine Nitriles, and X-ray Crystal Structure Analysis with Human Cathepsin L》 was written by Ehmke, Veronika; Winkler, Edwin; Banner, David W.; Haap, Wolfgang; Schweizer, W. Bernd; Rottmann, Matthias; Kaiser, Marcel; Freymond, Celine; Schirmeister, Tanja; Diederich, Francois. COA of Formula: C4H3F3N2This research focused onTrypanosoma rhodesain inhibitor triazine nitrile structure activity relationship. The article conveys some information:

The cysteine protease rhodesain of Trypanosoma brucei parasites causing African sleeping sickness has emerged as a target for the development of new drug candidates. Based on a triazine nitrile moiety as electrophilic headgroup, optimization studies on the substituents for the S1, S2, and S3 pockets of the enzyme were performed using structure-based design and resulted in inhibitors with inhibition constants in the single-digit nanomolar range. Comprehensive structure-activity relationships clarified the binding preferences of the individual pockets of the active site. The S1 pocket tolerates various substituents with a preference for flexible and basic side chains. Variation of the S2 substituent led to high-affinity ligands with inhibition constants down to 2 nM for compounds bearing cyclohexyl substituents. Systematic investigations on the S3 pocket revealed its potential to achieve high activities with aromatic vectors that undergo stacking interactions with the planar peptide backbone forming part of the pocket. X-ray crystal structure anal. with the structurally related enzyme human cathepsin L confirmed the binding mode of the triazine ligand series as proposed by mol. modeling. Sub-micromolar inhibition of the proliferation of cultured parasites was achieved for ligands decorated with the best substituents identified through the optimization cycles. In cell-based assays, the introduction of a basic side chain on the inhibitors resulted in a 35-fold increase in antitrypanosomal activity. Finally, bioisosteric imidazopyridine nitriles were studied to prevent off-target effects with unselective nucleophiles by decreasing the inherent electrophilicity of the triazine nitrile headgroup. Using this ligand, the stabilization by intramol. hydrogen bonding of the thioimidate intermediate, formed upon attack of the catalytic cysteine residue, compensates for the lower reactivity of the headgroup. The imidazopyridine nitrile ligand showed excellent stability toward the thiol nucleophile glutathione in a quant. in vitro assay and fourfold lower cytotoxicity than the parent triazine nitrile. After reading the article, we found that the author used 3-(Trifluoromethyl)-1H-pyrazole(cas: 20154-03-4COA of Formula: C4H3F3N2)

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Liao, Jia-Ling’s team published research in Inorganic Chemistry in 2015 | CAS: 20154-03-4

In 2015,Liao, Jia-Ling; Chi, Yun; Sie, Zong-Ting; Ku, Chia-Hao; Chang, Chih-Hao; Fox, Mark A.; Low, Paul J.; Tseng, Meu-Rurng; Lee, Gene-Hsiang published 《Ir(III)-Based Phosphors with Bipyrazolate Ancillaries; Rational Design, Photophysics, and Applications in Organic Light-Emitting Diodes》.Inorganic Chemistry published the findings.Recommanded Product: 20154-03-4 The information in the text is summarized as follows:

Three charge-neutral Ir(III) complexes bearing both neutral chelating ligands 4,4′-di-t-butyl-2,2′-bipyridine (dtbbpy) and monoanionic cyclometalated ligands derived from 2-phenylpyridine (ppyH), together with either 2 monoanionic ligands (i.e., chloride and monodentate pyrazolate) or a single dianionic chelate derived from 5,5′-di(trifluoromethyl)-3,3′-bipyrazole (bipzH2) or 5,5′-(1-methylethylidene)-bis-(3-trifluoromethyl-1H-pyrazole) (mepzH2), was successfully synthesized. These complexes are derived from a common, structurally characterized, Ir(III) intermediate complex [Ir(dtbbpy)(ppy)Cl2] (1), from treatment of IrCl3·3H2O with equal amount of the diimine (NN̂) and precursor of the cyclometalated (C^N) ligands in a form of 1-pot reaction. Treatment of 1 with various functional pyrazoles afforded [Ir(dtbbpy)(ppy)(pz)Cl] (2), [Ir(dtbbpy)(ppy)(bipz)] (3), and [Ir(dtbbpy)(ppy)(mepz)] (4), which display intense room-temperature emission with λmax spanning 532-593 nm in both fluid and solid states. The Ir(III) complexes, 3 and 4, showcase rare examples of 3 distinctive chelates (i.e., neutral, anionic, and dianionic) assembled around the central Ir(III) cation. Hybrid d. functional theory (DFT; B3LYP) electronic structure calculations on 1-4 reveal the LUMO to be π*(bpy) in character for all complexes and HOMO offering d(Ir)-π(phenyl) character for 1, 2, and 4 and π(bipz) character for 3. The different HOMO composition of 3 and 4 is also predicted by calculations using pure DFT (BLYP) and wave function (MP2) methods. From time-dependent DFT calculations, the emissive processes are dominated by the Ph group-to-bipyridine, ligand(ppy)-to-ligand(bpy) charge transfer admixed with metal-to-ligand transition for all Ir(III) complexes. Organic light emitting diodes were successfully fabricated. A double emitting layer design was adopted in the device architecture using Ir(III) metal complexes 3 and 4, attaining peak external quantum efficiencies, luminance efficiencies, and power efficiencies of 18.1% (59.0 cd/A and 38.6 lm/W) and 16.6% (53.3 cd/A and 33.5 lm/W), resp. The experimental process involved the reaction of 3-(Trifluoromethyl)-1H-pyrazole(cas: 20154-03-4Recommanded Product: 20154-03-4)

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics