Ward, D. D. et al. published their research in Journal of Chromatography in 1979 | CAS: 5334-39-4

3-Methyl-4-nitro-1H-pyrazole (cas: 5334-39-4) belongs to pyrazole derivatives. An alternative way to synthesize multisubstituted pyrazoles is the Csingle bondH arylation of simple pyrazoles. Pyrazole the presence of this nucleus in pharmacological agents of diverse therapeutic categories such as celecoxib, a potent anti-inflammatory, the antidepressant agent fezolamide have proved the pharmacological potential of the pyrazole moiety. Computed Properties of C4H5N3O2

Separation of pyrazoles by gas chromatography was written by Ward, D. D.;Grimmett, M. R.. And the article was included in Journal of Chromatography in 1979.Computed Properties of C4H5N3O2 This article mentions the following:

Pyrazole derivatives were separated by gas chromatog. by using glass columns (2.5 m × 1.5 mm) packed with silanized Chromosorb W (100-200 mesh) coated with 12% OV-17 or OV-225, N carrier gas at 20-25 cm3-min, inlet temperature 130-40°, a flame ionization detector at 300-50°, and temperature programming from 50° at 10°/min. Relative retention indexes and linear programmed indexes are given for alkyl-, 4-bromo-, 1-nitro-, C-nitro-, and bromonitropyrazoles. Although both N-substituted and N-unsubstituted pyrazoles could be separated on the same columns, 1-nitropyrazoles were sometimes susceptible to denitration at the higher temperatures used. In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitro-1H-pyrazole (cas: 5334-39-4Computed Properties of C4H5N3O2).

3-Methyl-4-nitro-1H-pyrazole (cas: 5334-39-4) belongs to pyrazole derivatives. An alternative way to synthesize multisubstituted pyrazoles is the Csingle bondH arylation of simple pyrazoles. Pyrazole the presence of this nucleus in pharmacological agents of diverse therapeutic categories such as celecoxib, a potent anti-inflammatory, the antidepressant agent fezolamide have proved the pharmacological potential of the pyrazole moiety. Computed Properties of C4H5N3O2

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

Hunziker, Daniel et al. published their research in Bioorganic & Medicinal Chemistry in 2004 | CAS: 45887-08-9

3-(1H-Pyrazol-3-yl)pyridine (cas: 45887-08-9) belongs to pyrazole derivatives. An alternative way to synthesize multisubstituted pyrazoles is the Csingle bondH arylation of simple pyrazoles. Pyrazole the presence of this nucleus in pharmacological agents of diverse therapeutic categories such as celecoxib, a potent anti-inflammatory, the antidepressant agent fezolamide have proved the pharmacological potential of the pyrazole moiety. Related Products of 45887-08-9

Novel ketolide antibiotics with a fused five-membered lactone ring – synthesis, physicochemical and antimicrobial properties was written by Hunziker, Daniel;Wyss, Pierre-C.;Angehrn, Peter;Mueller, Aranka;Marty, Hans-Peter;Halm, Remy;Kellenberger, Laurenz;Bitsch, Veronique;Biringer, Gerard;Arnold, Wolf;Stampfli, Andreas;Schmitt-Hoffmann, Anne;Cousot, Denis. And the article was included in Bioorganic & Medicinal Chemistry in 2004.Related Products of 45887-08-9 This article mentions the following:

In an effort to find novel semisynthetic macrolides with extended antibacterial spectrum and improved activity we prepared a series of compounds based on com. available clarithromycin, a potent and safe antimicrobial agent of outstanding clin. and com. interest. According to the literature, improvement of antibacterial activity of erythromycin type antibiotics can be achieved by introduction of fused heterocycles such as cyclic carbonates or carbamates at positions 11 and 12 (such as in telithromycin). In the course of the work presented here, a similar, hitherto unprecedented set of compounds bearing a five-membered lactone ring fused to positions 11 and 12 was prepared based on carbon-carbon bond formation via intramol. Michael addition of a [(hetero)arylalkylthio]acetic acid ester enolate to an α,β-unsaturated ketone as the key step. Some of the ketolide compounds described in this paper were highly active against a representative set of erythromycin sensitive and erythromycin resistant test strains. The best compound showed a similar antimicrobial spectrum and comparable activity in vitro as well as in vivo as telithromycin. Furthermore, some physicochem. properties of these compounds were determined and are presented here. On the basis of these results, the novel ketolide lactones presented in this paper emerged as valuable lead compounds with comparable properties as the com. ketolide antibacterial telithromycin (KetekTM). In the experiment, the researchers used many compounds, for example, 3-(1H-Pyrazol-3-yl)pyridine (cas: 45887-08-9Related Products of 45887-08-9).

3-(1H-Pyrazol-3-yl)pyridine (cas: 45887-08-9) belongs to pyrazole derivatives. An alternative way to synthesize multisubstituted pyrazoles is the Csingle bondH arylation of simple pyrazoles. Pyrazole the presence of this nucleus in pharmacological agents of diverse therapeutic categories such as celecoxib, a potent anti-inflammatory, the antidepressant agent fezolamide have proved the pharmacological potential of the pyrazole moiety. Related Products of 45887-08-9

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

Elguero, Jose et al. published their research in Compt. Rend. in 1965 | CAS: 934-48-5

3,5-Dimethyl-1H-pyrazole-1-carboxamide (cas: 934-48-5) belongs to pyrazole derivatives. Pyrazole is a weak base, with pKb 11.5 (pKa of the conjugated acid 2.49 at 25 °C).Pyrazole used as a ligand to prepare organometallic compounds. Pyrazoles and pyrimidines have diverse biological and pharmacological activities. There are a number of antimicrobial compounds containing pyrazole moiety as the core unit. Pyrazofurin is important antimicrobial drug and 2-methylpyrimidine-4-ylamine derivatives I and II were found to be effective inhibitors of Escherichia coli PDHc-E1 with antibacterial and antifungal activity.Category: pyrazoles-derivatives

Investigation of azoles. N-Carbamoylpyrazoles was written by Elguero, Jose;Jacquier, Robert. And the article was included in Compt. Rend. in 1965.Category: pyrazoles-derivatives This article mentions the following:

A series of 3- and 5-methyl-1-carbamoylpyrazoles, obtained from H2NCONHNH2.HCl with various acetoacetaldehyde derivatives, were identified by their N.M.R. and uv spectra. Several symmetrically substituted N-carbamoylpyrazoles were also studied. 1-Carbamoylpyrazole (I), m. 140-1°, with Br in CHCl3 gave the 4-Br derivative of I, m. 187-9° (EtOH). 3,5-Dimethyl-1-carbamoylpyrazole, m. 113.5°, gave similarly the 4-Br derivative, m. 152-3°. The mixture, m. 98-9°, obtained from H2NCONHNH2.HCl with (MeO)2CHCH2Ac, contained, according to its N.M.R. spectrum, 40% 3-Me derivative of I and 60% 5-Me derivative of I, and according to its uv spectrum 43 and 57%, resp. In the experiment, the researchers used many compounds, for example, 3,5-Dimethyl-1H-pyrazole-1-carboxamide (cas: 934-48-5Category: pyrazoles-derivatives).

3,5-Dimethyl-1H-pyrazole-1-carboxamide (cas: 934-48-5) belongs to pyrazole derivatives. Pyrazole is a weak base, with pKb 11.5 (pKa of the conjugated acid 2.49 at 25 °C).Pyrazole used as a ligand to prepare organometallic compounds. Pyrazoles and pyrimidines have diverse biological and pharmacological activities. There are a number of antimicrobial compounds containing pyrazole moiety as the core unit. Pyrazofurin is important antimicrobial drug and 2-methylpyrimidine-4-ylamine derivatives I and II were found to be effective inhibitors of Escherichia coli PDHc-E1 with antibacterial and antifungal activity.Category: pyrazoles-derivatives

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

Wen, Jun et al. published their research in Tetrahedron in 2011 | CAS: 73387-46-9

3-(4-Bromophenyl)-1H-pyrazole (cas: 73387-46-9) belongs to pyrazole derivatives. The 1H-pyrazole provides an excellent means by which to provide the requisite hydrogen bond acceptor–donor motifs, whether as a monocyclic ring or as a fused indazole ring. Pyrazoles are commonly used scaffold molecules in drug discovery projects. The use of pyrazole derivatives is based on their analgesic, anti-inflammatory, antipyretic, antiarrhythmic, sedative, muscle relaxant, neuroleptic, anticonvulsant, monoamine oxidase inhibitory, antidiabetic and antibacterial activities.Reference of 73387-46-9

A simple and efficient synthesis of pyrazoles in water was written by Wen, Jun;Fu, Yun;Zhang, Ruo-Yi;Zhang, Ji;Chen, Shan-Yong;Yu, Xiao-Qi. And the article was included in Tetrahedron in 2011.Reference of 73387-46-9 This article mentions the following:

A simple, highly efficient, and environmentally friendly method for the synthesis of substituted 1H-pyrazoles by one-pot condensation reaction of α,β-unsaturated carbonyl compounds with tosyl hydrazide in water was developed. The reaction system exhibited tolerance with various functional groups. Aromatic moieties with both electron-rich and electron-deficient substituents gave desired products in good to excellent yields. In the experiment, the researchers used many compounds, for example, 3-(4-Bromophenyl)-1H-pyrazole (cas: 73387-46-9Reference of 73387-46-9).

3-(4-Bromophenyl)-1H-pyrazole (cas: 73387-46-9) belongs to pyrazole derivatives. The 1H-pyrazole provides an excellent means by which to provide the requisite hydrogen bond acceptor–donor motifs, whether as a monocyclic ring or as a fused indazole ring. Pyrazoles are commonly used scaffold molecules in drug discovery projects. The use of pyrazole derivatives is based on their analgesic, anti-inflammatory, antipyretic, antiarrhythmic, sedative, muscle relaxant, neuroleptic, anticonvulsant, monoamine oxidase inhibitory, antidiabetic and antibacterial activities.Reference of 73387-46-9

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

Dorn, Helmut et al. published their research in Chemische Berichte in 1966 | CAS: 3528-58-3

1-Ethyl-1H-pyrazol-5-amine (cas: 3528-58-3) belongs to pyrazole derivatives. The strategies for the synthesis of pyrazoles generally can be applied for the construction of indazoles. Pyrazole rings have been used as core components of several leading non-steroidal anti-inflammatory drugs (NSAIDs) and antihypertensive drugs. It has also been found to be useful as a bifunctional ligand for metal catalysis.COA of Formula: C5H9N3

Redox cleavage of sulfonamides. V. Structure of the bis-(arylsulfonyl) derivatives of 5-amino-1-methylpyrazole was written by Dorn, Helmut;Hilgetag, Guenter;Zubek, Alfred. And the article was included in Chemische Berichte in 1966.COA of Formula: C5H9N3 This article mentions the following:

Bis(arylsulfonyl) derivatives of 5-amino-1-methylpyrazole formed from 5-amino-1-methylpyrazole (I) and the 5-SO2NH2 analog of I in C5H5N were shown by spectroscopic and chem. evidence to carry the 2 sulfonyl groups on the exocyclic N atom. II (Ar = Ph or p-ClC6H4) (0.004 mole) in 16 cc. dry C5H5N shaken 48 hrs. at room temperature with 0.0043 mole Ar’SO2Cl (Ar’ = p-ClC6H4 or p-MeC6H4) and poured onto ice and 80 cc. 2N HCl gave the following III (Ar, Ar’, % yield, and m.p. given): Ph, p-ClC6H4, (IV), 81.5, 128-9°; Ph, p-MeC6H4 (V), 85.0, 116-17°; p-ClC6H4, p-MeC6H4, (VI), 74.2, 171-2°. The same compounds were also prepared in a similar manner from the II (Ar = p-ClC6H4 or p-MeC6H4) with the Ar’SO2Cl (Ar’ = Ph or p-ClC5H4) (% given): IV 51.2, V 62.4, VI 65.8. The uv spectra of 5-(p-toluenesulfonamino)-1-methylpyrazole, V, and VI are recorded. In the experiment, the researchers used many compounds, for example, 1-Ethyl-1H-pyrazol-5-amine (cas: 3528-58-3COA of Formula: C5H9N3).

1-Ethyl-1H-pyrazol-5-amine (cas: 3528-58-3) belongs to pyrazole derivatives. The strategies for the synthesis of pyrazoles generally can be applied for the construction of indazoles. Pyrazole rings have been used as core components of several leading non-steroidal anti-inflammatory drugs (NSAIDs) and antihypertensive drugs. It has also been found to be useful as a bifunctional ligand for metal catalysis.COA of Formula: C5H9N3

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

O’Callaghan, C. N. et al. published their research in Proceedings of the Royal Irish Academy in 1974 | CAS: 934-48-5

3,5-Dimethyl-1H-pyrazole-1-carboxamide (cas: 934-48-5) belongs to pyrazole derivatives. The strategies for the synthesis of pyrazoles generally can be applied for the construction of indazoles. The pyrazole ring is resistant to oxidation and reduction but the groups, such as alkyl and formyl attached to the ring, are oxidized to respective acids. Only electrolytic oxidation, ozonolysis, and a strong base cause ring opening.Recommanded Product: 934-48-5

Anticancer agents. X. Cyclization of 1-acyl-4-alkylthiosemicarbazide derivatives to 1,2,4,-triazoline-3-thiones in the presence of hydrazine was written by O’Callaghan, C. N.. And the article was included in Proceedings of the Royal Irish Academy, Section B: Biological, Geological and Chemical Science in 1974.Recommanded Product: 934-48-5 This article mentions the following:

The triazolethione I [R = Et, Bu, Me(CH2)7, MeCONH] were prepared by cyclization of RCH(CONHNHCSNHMe)2 with H2NNH2. EtO2CCHRCONHNHCSNHMe (R = H, Et, Bu) and H2NNH2 gave the triazolethiones II (R = CH2CONHNH2, CHEtCONHNH2, CHBuCONHNH; R1 = Me). RCONHNHCSNHR1 (R = CH2CO2Et, R1 = Et, PhCH2; R = CO2Et, R1 = Me) and H2NNH2 gave the corresponding hydrazides which were cyclized with NaOH to give II (R = CH2CONHNH2, R1 = Et, PhCH2; R = CONHNH2, R1 = Me). In the experiment, the researchers used many compounds, for example, 3,5-Dimethyl-1H-pyrazole-1-carboxamide (cas: 934-48-5Recommanded Product: 934-48-5).

3,5-Dimethyl-1H-pyrazole-1-carboxamide (cas: 934-48-5) belongs to pyrazole derivatives. The strategies for the synthesis of pyrazoles generally can be applied for the construction of indazoles. The pyrazole ring is resistant to oxidation and reduction but the groups, such as alkyl and formyl attached to the ring, are oxidized to respective acids. Only electrolytic oxidation, ozonolysis, and a strong base cause ring opening.Recommanded Product: 934-48-5

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

Yu, Yue et al. published their research in Green Chemistry in 2016 | CAS: 45887-08-9

3-(1H-Pyrazol-3-yl)pyridine (cas: 45887-08-9) belongs to pyrazole derivatives. An alternative way to synthesize multisubstituted pyrazoles is the Csingle bondH arylation of simple pyrazoles. Protonation of pyrazole in strong acid leads to pyrazolium cations, which undergo electrophilic substitution preferentially at C3 rather than C4. The pyrazole anion is not reactive toward nucleophiles but is mostly reactive to electrophiles.Recommanded Product: 3-(1H-Pyrazol-3-yl)pyridine

Calcium carbide as the acetylide source: transition-metal-free synthesis of substituted pyrazoles via [1,5]-sigmatropic rearrangements was written by Yu, Yue;Huang, Wei;Chen, Yang;Gao, Bingjie;Wu, Wanqing;Jiang, Huanfeng. And the article was included in Green Chemistry in 2016.Recommanded Product: 3-(1H-Pyrazol-3-yl)pyridine This article mentions the following:

Under transition-metal-free conditions, N-tosylhydrazones derived from aldehydes or ketones were reacted with an acetylide source, calcium carbide to afford 3-substituted pyrazoles I [R1 = C6H5, 3-BrC6H4, H4C6(CH2)2, 2-thienyl, etc.; R2 = H] and 3,4-disubstituted pyrazoles I [R1 = Me, Et, n-Pr, C6H5; R2 = C6H5, 4-F3CC6H4, 2-naphthyl, etc.] resp. in good yields with high regioselectivities. The results of deuterium-labeling experiments indicated that these reactions proceed through [3 + 2] cycloadditions followed by [1,5]-sigmatropic rearrangements. In the experiment, the researchers used many compounds, for example, 3-(1H-Pyrazol-3-yl)pyridine (cas: 45887-08-9Recommanded Product: 3-(1H-Pyrazol-3-yl)pyridine).

3-(1H-Pyrazol-3-yl)pyridine (cas: 45887-08-9) belongs to pyrazole derivatives. An alternative way to synthesize multisubstituted pyrazoles is the Csingle bondH arylation of simple pyrazoles. Protonation of pyrazole in strong acid leads to pyrazolium cations, which undergo electrophilic substitution preferentially at C3 rather than C4. The pyrazole anion is not reactive toward nucleophiles but is mostly reactive to electrophiles.Recommanded Product: 3-(1H-Pyrazol-3-yl)pyridine

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

Scott, Francis L. et al. published their research in Chemistry & Industry (London, United Kingdom) in 1956 | CAS: 934-48-5

3,5-Dimethyl-1H-pyrazole-1-carboxamide (cas: 934-48-5) belongs to pyrazole derivatives. Pyrazole has two ring nitrogen atoms in which N1 is pyrrolic and N2 is pyridine-like. The N1 nitrogen is not reactive but is deprotonated in the presence of a base-forming anion. The pyrazole ring is resistant to oxidation and reduction but the groups, such as alkyl and formyl attached to the ring, are oxidized to respective acids. Only electrolytic oxidation, ozonolysis, and a strong base cause ring opening.Related Products of 934-48-5

Nitrogen systems. VI. Some nucleophilic displacements on 1-carbamoylpyrazoles was written by Scott, Francis L.. And the article was included in Chemistry & Industry (London, United Kingdom) in 1956.Related Products of 934-48-5 This article mentions the following:

ZCSNH2 (throughout this abstract Z = 3,5-dimethyl-1-pyrazolyl) (I) refluxed in EtOH with RNH2 [R = Bu] (II), cyclohexyl (III), Ph2NCONH, H2O.NH2, or PhNHNH2 (IV)], morpholine (V), or piperidine (VI) gave the corresponding monosubstituted thiourea. I with aniline (VII) or benzylamine the sym. disubstituted thiourea. ZC(:NH)NHR [R = Bz (VIII), SO2C6H4Me-p (IX), and CSNHPh (X)] were unaffected by II, III, IV, V, or VI in EtOH, but, in the absence of EtOH, VIII on refluxing with II, III, VI, or VII gave the corresponding Bz derivatives of the mono substituted guanidines and with V gave both 4-(benzoylguanyl)morpholine and BzN:CR2(R = morpholino). Similarly IX refluxed with II, III, IV, V or VI in the absence of EtOH gave the p-tolylsulfonyl derivatives of the corresponding monosubstituted guanidines. ZC(:NH)NHC(SMe):NR.HI or its 4-Cl or 4-Br derivative (R = Ph) on refluxing in EtOH with amines gives very little reaction, but refluxing with II, III, or V in the absence of EtOH gives RC(:NH)NHC(SMe):NPh (R = the corresponding amino group), α-C10H7NHCONHC(:NH)Z in EtOH refluxed with II, III, IV, V, or VI gives the corresponding α-naphthyl ureas and ZH. Use of an azide ion gives with ZC(:NH)NHR(R = H or NO2) 5-amino- and 5-nitraminotetrazoles, resp. Cf. C.A. 47, 6886a, 8670g, 9923c. In the experiment, the researchers used many compounds, for example, 3,5-Dimethyl-1H-pyrazole-1-carboxamide (cas: 934-48-5Related Products of 934-48-5).

3,5-Dimethyl-1H-pyrazole-1-carboxamide (cas: 934-48-5) belongs to pyrazole derivatives. Pyrazole has two ring nitrogen atoms in which N1 is pyrrolic and N2 is pyridine-like. The N1 nitrogen is not reactive but is deprotonated in the presence of a base-forming anion. The pyrazole ring is resistant to oxidation and reduction but the groups, such as alkyl and formyl attached to the ring, are oxidized to respective acids. Only electrolytic oxidation, ozonolysis, and a strong base cause ring opening.Related Products of 934-48-5

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

Vicentini, Chiara B. et al. published their research in Journal of Agricultural and Food Chemistry in 2002 | CAS: 141459-53-2

1-(tert-Butyl)-3-methyl-1H-pyrazol-5-amine (cas: 141459-53-2) belongs to pyrazole derivatives. Pyrazole and its derivatives are considered a pharmacologically important active scaffold that possesses almost all types of pharmacological activities. Pyrazole the presence of this nucleus in pharmacological agents of diverse therapeutic categories such as celecoxib, a potent anti-inflammatory, the antidepressant agent fezolamide have proved the pharmacological potential of the pyrazole moiety. COA of Formula: C8H15N3

Development of new fungicides against Magnaporthe grisea: synthesis and biological activity of pyrazolo[3,4-d][1,3]thiazine, pyrazolo[1,5-c][1,3,5]thiadiazine, and pyrazolo[3,4-d]pyrimidine derivatives was written by Vicentini, Chiara B.;Forlani, Giuseppe;Manfrini, Maurizio;Romagnoli, Carlo;Mares, Donatella. And the article was included in Journal of Agricultural and Food Chemistry in 2002.COA of Formula: C8H15N3 This article mentions the following:

Some pyrazolo[3,4-d]pyrimidin-4(5H)-thione, pyrazolo[3,4-d][1,3]thiazin-4-one/thione, and pyrazolo[1,5-c][1,3,5]thiadiazine-4-one/thione derivatives were synthesized and screened for antifungal activity against the causal agent of rice blast disease, Magnaporthe grisea. In all cases a remarkable inhibition of fungal growth was found in the range from 10 to 200 μg mL-1. Several compounds were able to control mycelial growth at a rate of 10 μg mL-1, a concentration at which the reference compound tricyclazole was completely ineffective. At least in the case of the most active substance, at the same dose the growth of seedlings or cultured cells of rice was substantially unaffected. Results allowed definition of structural requirements either to maintain or to enhance mycotoxic activity. In the experiment, the researchers used many compounds, for example, 1-(tert-Butyl)-3-methyl-1H-pyrazol-5-amine (cas: 141459-53-2COA of Formula: C8H15N3).

1-(tert-Butyl)-3-methyl-1H-pyrazol-5-amine (cas: 141459-53-2) belongs to pyrazole derivatives. Pyrazole and its derivatives are considered a pharmacologically important active scaffold that possesses almost all types of pharmacological activities. Pyrazole the presence of this nucleus in pharmacological agents of diverse therapeutic categories such as celecoxib, a potent anti-inflammatory, the antidepressant agent fezolamide have proved the pharmacological potential of the pyrazole moiety. COA of Formula: C8H15N3

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

Svistunova, I. V. et al. published their research in Russian Journal of General Chemistry in 2008 | CAS: 15953-73-8

4-Chloro-3,5-dimethyl-1H-pyrazole (cas: 15953-73-8) belongs to pyrazole derivatives. The 1H-pyrazole provides an excellent means by which to provide the requisite hydrogen bond acceptor–donor motifs, whether as a monocyclic ring or as a fused indazole ring. Protonation of pyrazole in strong acid leads to pyrazolium cations, which undergo electrophilic substitution preferentially at C3 rather than C4. The pyrazole anion is not reactive toward nucleophiles but is mostly reactive to electrophiles.HPLC of Formula: 15953-73-8

α-Substituted boron difluoride acetylacetonates was written by Svistunova, I. V.;Fedorenko, E. V.. And the article was included in Russian Journal of General Chemistry in 2008.HPLC of Formula: 15953-73-8 This article mentions the following:

By treatment of α-substituted acetylacetone derivatives with boron trifluoride etherate, a series of earlier unknown boron difluoride complexes is obtained. The series includes binuclear complexes containing boron in the chelate fragment connected via sulfur or selenium atoms. Gas chromatog. and spectral characteristics of the obtained compounds were investigated. By means of chromato-mass spectrometry their reaction with hydrazine in acidic and alk. media was studied. In the experiment, the researchers used many compounds, for example, 4-Chloro-3,5-dimethyl-1H-pyrazole (cas: 15953-73-8HPLC of Formula: 15953-73-8).

4-Chloro-3,5-dimethyl-1H-pyrazole (cas: 15953-73-8) belongs to pyrazole derivatives. The 1H-pyrazole provides an excellent means by which to provide the requisite hydrogen bond acceptor–donor motifs, whether as a monocyclic ring or as a fused indazole ring. Protonation of pyrazole in strong acid leads to pyrazolium cations, which undergo electrophilic substitution preferentially at C3 rather than C4. The pyrazole anion is not reactive toward nucleophiles but is mostly reactive to electrophiles.HPLC of Formula: 15953-73-8

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