10010-93-2

Usage

Uses

Used in Pharmaceutical Industry:
3-Methyl-5-(trifluoromethyl)pyrazole is used as a reagent for the preparation of (fluoromethyl)pyrazole via microwave-assisted Stille coupling. This application is significant in the pharmaceutical industry as it aids in the synthesis of various compounds with potential therapeutic applications.
Used in Chemical Synthesis:
3-Methyl-5-(trifluoromethyl)pyrazole is also used in chemical synthesis, particularly for the creation of new compounds with potential applications in various fields, such as materials science, agrochemicals, and pharmaceuticals. Its unique structure and properties make it a valuable building block for the development of novel molecules with specific functions and activities.

InChI:InChI=1/C5H5F3N2/c1-3-2-4(10-9-3)5(6,7)8/h2H,1H3,(H,9,10)

Synthetic route

1,1,1-Trifluoro-2,4-pentanedione (367-57-7) → 5-methyl-3-trifluoromethyl-1H-pyrazole (10010-93-2)

Conditions	Yield
With hydrazine In methanol at 0 - 20℃; for 16h;	95%
Stage #1: 1,1,1-Trifluoro-2,4-pentanedione With hydrazine hydrate In chloroform for 1h; Reflux; Stage #2: With phosphorus pentoxide In chloroform for 3h; Reflux;	90%
With hydrazine hydrate In ethanol at 0℃; for 6h; Reflux; Inert atmosphere;	82%

1-(1-pyrrolidinomethyl)-3-trifluoromethylpyrazole (155635-51-1) + methyl iodide (74-88-4) → 5-methyl-3-trifluoromethyl-1H-pyrazole (10010-93-2)

Conditions	Yield
With n-butyllithium 1.) THF, -70 deg C, 2 h, 2.) THF, from -70 deg C to r.t.; Yield given. Multistep reaction;

1,1,1-Trifluoro-2,4-pentanedione (367-57-7) → 3-methyl-5-(trifluoromethyl)pyrazole (10010-93-2) + 5-methyl-3-trifluoromethyl-1H-pyrazole (10010-93-2)

Conditions	Yield
Stage #1: 1,1,1-Trifluoro-2,4-pentanedione With hydrazine In 1,4-dioxane Stage #2: In toluene Heating; Further stages.;

(Z)-9-octadecen-1-amine (112-90-3) + C15H12F9N6P → C54H108N3P + 5-methyl-3-trifluoromethyl-1H-pyrazole (10010-93-2)

Conditions	Yield
at 50℃; for 0.0833333h;

5-methyl-3-trifluoromethyl-1H-pyrazole (10010-93-2) → 4-bromo-5-methyl-3-(trifluoromethyl)-1H-pyrazole (60061-68-9)

Conditions	Yield
With bromine; sodium acetate; acetic acid at 0 - 20℃; for 21.1667h;	100%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 25℃; for 1h;	99%

5-methyl-3-trifluoromethyl-1H-pyrazole (10010-93-2) + silver(l) oxide (20667-12-3) → ([3-(CF3),5-(Me)Pz]Ag)3 (937255-69-1)

Conditions	Yield
In toluene (N2, dark); refluxing overnight mixt. of pyrazole deriv. and silver oxide in toluene; cooling filtration through celite, evapn., elem. anal.;	95%

sodium tetrahydroborate (16940-66-2) + 5-methyl-3-trifluoromethyl-1H-pyrazole (10010-93-2) → sodium hydrotris(3-trifluoromethyl-5-methyl-1-pyrazolyl)borate

Conditions	Yield
at 130℃; for 4h;	92%
In kerosene byproducts: H2; 5 equiv. of substituted pyrazole, slow heating to 220°C until evolution of stoich. amt. of H2; cooling to 180°C, collection (filtration), washing (petroleum ether), drying (high vac.); elem. anal.;	58%

copper(I) oxide + 5-methyl-3-trifluoromethyl-1H-pyrazole (10010-93-2) → [tris(3-trifluoromethyl-5-methylpyrazolate)tricopper(I)] (854763-47-6)

Conditions	Yield
With acetonitrile In benzene under N2; CH3CN added to mixt. of Cu2O and pyrazole derivative in benzene, mixt. refluxed for 12 h; cooled, filtered through Celite, filtrate evapd. under vac.; elem. anal.;	92%

bromoacetic acid methyl ester (96-32-2) + 5-methyl-3-trifluoromethyl-1H-pyrazole (10010-93-2) → methyl 2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 18h;	91%

1-ferrocenylethanol (1277-49-2) + 5-methyl-3-trifluoromethyl-1H-pyrazole (10010-93-2) → ferrocenyl(ethyl)-1N-(3-trifluoromethyl-5-methyl)pyrazole (654083-42-8)

Conditions	Yield
With tetrafluoroboric acid In dichloromethane; water addn. of aq. HBF4 to a mixt. of iron complex and heterocycle in CH2Cl2, stirring for 5 min; addn. of Et2O, water, ascorbic acid, sepn., washing org. phase with coldwater, evapn. drying over CaCl2;	88%

5-methyl-3-trifluoromethyl-1H-pyrazole (10010-93-2) + Ethyl 2-bromopropionate (535-11-5, 41978-69-2) → C10H13F3N2O2 (1007487-64-0)

Conditions	Yield
With potassium carbonate In tetrahydrofuran; N,N-dimethyl-formamide at 60℃; for 5h;	88%

5-bromo-2-pyridylamine (1072-97-5) + 5-methyl-3-trifluoromethyl-1H-pyrazole (10010-93-2) → 5-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-amine (1415640-68-4)

Conditions	Yield
With potassium phosphate; copper(l) iodide; cis-N,N'-dimethyl-1,2-diaminocyclohexane In 1,4-dioxane at 130℃; Schlenk technique; Inert atmosphere;	88%

(S)-1-hydroxyethylferrocene + 5-methyl-3-trifluoromethyl-1H-pyrazole (10010-93-2) → (S)-(3-trifluoromethyl-5-methylpyrazolyl)-α-ethylferrrocene

Conditions	Yield
With tetrafluoroboric acid In dichloromethane; water at 22 - 25℃; for 0.0833333h; enantiospecific reaction;	88%

5-bromo-4-methoxy-1,1,1-trifluoro-pent-3-en-2-one (502926-95-6) + 5-methyl-3-trifluoromethyl-1H-pyrazole (10010-93-2) → 1-(3-methoxy-5-(trifluoromethyl)-2,3-dihydrofuran-3-yl)-5-methyl-3-(trifluoromethyl)-1H-pyrazole

Conditions	Yield
Stage #1: 5-methyl-3-trifluoromethyl-1H-pyrazole With potassium carbonate In acetonitrile at 20℃; for 0.333333h; Stage #2: 5-bromo-4-methoxy-1,1,1-trifluoro-pent-3-en-2-one In acetonitrile for 2h; Solvent; Reflux;	86%

5-bromo-4-(diethylamino)-1,1,1-trifluoropent-3-en-2-one + 5-methyl-3-trifluoromethyl-1H-pyrazole (10010-93-2) → (E)-4-(diethylamino)-1,1,1-trifluoro-5-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pent-3-en-2-one

Conditions	Yield
Stage #1: 5-methyl-3-trifluoromethyl-1H-pyrazole With potassium carbonate In acetonitrile at 20℃; for 0.333333h; Stage #2: 5-bromo-4-(diethylamino)-1,1,1-trifluoropent-3-en-2-one In acetonitrile for 5h; Reflux;	85%

5-methyl-3-trifluoromethyl-1H-pyrazole (10010-93-2) + 2-bromobutyric acid ethyl ester (533-68-6) → C11H15F3N2O2

Conditions	Yield
With potassium carbonate In tetrahydrofuran; N,N-dimethyl-formamide at 60℃; for 5h;	84%

(2S,4R)-4-(4-fluoro-2-trifluoromethylbenzenesulfonyl)-1-(1-trifluoromethylcyclopropanecarbonyl)pyrrolidine-2-carboxylic acid (1-cyanocyclopropyl)amide (1252637-02-7) + 5-methyl-3-trifluoromethyl-1H-pyrazole (10010-93-2) → (2S,4R)-4-[4-(5-methyl-3-trifluoromethylpyrazol-1-yl)-2-trifluoromethylbenzenesulfonyl]-1-(1-trifluoromethylcyclopropanecarbonyl)pyrrolidine-2-carboxylic acid (1-cyanocyclopropyl)amide

Conditions	Yield
With caesium carbonate In N,N-dimethyl acetamide at 22℃; for 72h;	84%

2-chloro-1-(1-(4-chloro-3-methoxyphenyl)piperidin-4-yl)ethanone (1018324-03-2) + 5-methyl-3-trifluoromethyl-1H-pyrazole (10010-93-2) → 1-(1-(4-chloro-3-methoxyphenyl)piperidin-4-yl)-2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)ethanone (1018325-07-9)

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; for 12h;	81%

3-bromo-1-[1-(4-fluorophenyl)-5-isopropylpyrazol-4-yl]pyrrolidin-2-one (1613396-19-2) + 5-methyl-3-trifluoromethyl-1H-pyrazole (10010-93-2) → 1-[1-(4-fluorophenyl)-5-isopropylpyrazol-4-yl]-3-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]pyrrolidin-2-one (1613395-15-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 1h;	80%

C8H10BrF3O2 + 5-methyl-3-trifluoromethyl-1H-pyrazole (10010-93-2) → 5-methyl-1-(3-propoxy-5-(trifluoromethyl)-2,3-dihydrofuran-3-yl)-3-(trifluoromethyl)-1H-pyrazole

Conditions	Yield
Stage #1: 5-methyl-3-trifluoromethyl-1H-pyrazole With potassium carbonate In acetonitrile at 20℃; for 0.333333h; Stage #2: C8H10BrF3O2 In acetonitrile for 2h; Reflux;	80%

6-bromopyridine-3-amine (13534-97-9) + 5-methyl-3-trifluoromethyl-1H-pyrazole (10010-93-2) → 6-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]pyridin-3-amine (1006961-49-4)

Conditions	Yield
With potassium phosphate; copper(l) iodide In 1,4-dioxane at 130℃; Inert atmosphere; Schlenk technique;	79%

4-oxo-4-phenyl-but-2-ynoic acid ethyl ester (54966-47-1) + 5-methyl-3-trifluoromethyl-1H-pyrazole (10010-93-2) → 2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-4-oxo-4-phenyl-butyric acid ethyl ester

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 16h;	78%

5-bromo-1,1,1-trifluoro-4-(pyrrolidin-1-yl)pent-3-en-2-one + 5-methyl-3-trifluoromethyl-1H-pyrazole (10010-93-2) → (E)-1,1,1-trifluoro-5-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)-4-(pyrrolidin-1-yl)pent-3-en-2-one

Conditions	Yield
Stage #1: 5-methyl-3-trifluoromethyl-1H-pyrazole With potassium carbonate In acetonitrile at 20℃; for 0.333333h; Stage #2: 5-bromo-1,1,1-trifluoro-4-(pyrrolidin-1-yl)pent-3-en-2-one In acetonitrile for 5h; Reflux;	78%

bis[bis(trimethylsilyl)amino]germanium(II) (59863-12-6) + 5-methyl-3-trifluoromethyl-1H-pyrazole (10010-93-2) → [Ge(HC3N2(CF3)CH3)2]2

Conditions	Yield
In hexane (under Ar, Schlenk); soln. of ligand in hexane added dropwise to soln. of Ge-compound in hexane at room temp.; treated with toluene, heated at 60°C, stored for 16 h at -20°C;	77%

5-bromo-4-ethoxy-1,1,1-trifluoropent-3-en-2-one (910858-21-8) + 5-methyl-3-trifluoromethyl-1H-pyrazole (10010-93-2) → 1-(3-ethoxy-5-(trifluoromethyl)-2,3-dihydrofuran-3-yl)-5-methyl-3-(trifluoromethyl)-1H-pyrazole

Conditions	Yield
Stage #1: 5-methyl-3-trifluoromethyl-1H-pyrazole With potassium carbonate In acetonitrile at 20℃; for 0.333333h; Stage #2: 5-bromo-4-ethoxy-1,1,1-trifluoropent-3-en-2-one In acetonitrile for 2h; Reflux;	76%

5-bromo-4-(dibutylamino)-1,1,1-trifluoropent-3-en-2-one + 5-methyl-3-trifluoromethyl-1H-pyrazole (10010-93-2) → (E)-4-(dibutylamino)-1,1,1-trifluoro-5-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pent-3-en-2-one

Conditions	Yield
Stage #1: 5-methyl-3-trifluoromethyl-1H-pyrazole With potassium carbonate In acetonitrile at 20℃; for 0.333333h; Stage #2: 5-bromo-4-(dibutylamino)-1,1,1-trifluoropent-3-en-2-one In acetonitrile for 5h; Reflux;	73%

2-Fluorobenzaldehyde (446-52-6) + 5-methyl-3-trifluoromethyl-1H-pyrazole (10010-93-2) → C12H7F3N2 (1422280-85-0)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 120℃; for 96h;	71%

C10H13BrF3NO + 5-methyl-3-trifluoromethyl-1H-pyrazole (10010-93-2) → (E)-1,1,1-trifluoro-5-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)-4-(piperidin-1-yl)pent-3-en-2-one

Conditions	Yield
Stage #1: 5-methyl-3-trifluoromethyl-1H-pyrazole With potassium carbonate In acetonitrile at 20℃; for 0.333333h; Stage #2: C10H13BrF3NO In acetonitrile for 5h; Reflux;	71%

[Pt(P(C2H5)3)2(Cl)]2(2+)*2BF4(1-) = [Pt(P(C2H5)3)2(Cl)]2(BF4)2 + 5-methyl-3-trifluoromethyl-1H-pyrazole (10010-93-2) → cis-chlorobis(triethylphosphine)(3-(trifluoromethyl)-5-methylpyrazole)platinum(II) tetrafluoroborate (84049-91-2)

Conditions	Yield
In acetone organic compd. added to Pt complex in acetone, stirred at room temp. for 5 h; evapn., recrystn. (CH2Cl2-pentane);	70%

cis-dichlorobis(triethylphosphine)platinum(II) (13965-02-1, 14177-93-6, 15692-07-6) + 5-methyl-3-trifluoromethyl-1H-pyrazole (10010-93-2) → cis-Pt(PEt3)2(NCMeCHC(CF3)N)2 (84049-92-3)

Conditions	Yield
With KOH In methanol KOH added to soln. of Pt complex and organci compd. in MeOH, stirred for 1 h; extn. (CH2Cl2), filtration, evapn., addition of pentane, cooling;	70%

C6H7BrF3NO + 5-methyl-3-trifluoromethyl-1H-pyrazole (10010-93-2) → (E)-4-(dimethylamino)-1,1,1-trifluoro-5-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pent-3-en-2-one

Conditions	Yield
Stage #1: 5-methyl-3-trifluoromethyl-1H-pyrazole With potassium carbonate In acetonitrile at 20℃; for 0.333333h; Stage #2: C6H7BrF3NO In acetonitrile for 5h; Reflux;	70%

ethyl 4-hydroxy-4-(4-methoxyphenyl)but-2-ynoate + 5-methyl-3-trifluoromethyl-1H-pyrazole (10010-93-2) → 4-(4-methoxy-phenyl)-2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-4-oxo-butyric acid ethyl ester

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 16h;	68%

Upstream product

• 135351-20-1 (3E)-1,1,1-trifluoro-4-methoxy-pent-3-en-2-one 
• 367-57-7 1,1,1-Trifluoro-2,4-pentanedione 
• 106578-68-1 (Z)-1,1,1-trifluoro-4-(phenylamino)pent-3-en-2-one 
• 35179-63-6 5-hydroxy-3-methyl-5-trifluoromethyl-4,5-dihydro-1H-pyrazolethiocarboxy amide 
• 135351-20-1 1,1,1-trifluoro-4-methoxypent-3-en-2-one 
• 140-87-4 Cyanoacetohydrazide 
• 1453-58-3 3-Methylpyrazole 
• 2314-97-8 iodotrifluoromethane 
• 6294-89-9 hydrazinecarboxylic acid methyl ester 
• 55819-76-6 2'-acetyl-2-cyanoaceto-hydrazide 
• 155635-51-1 1-(1-pyrrolidinomethyl)-3-trifluoromethylpyrazole 
• 74-88-4 methyl iodide 
• 112-90-3 (Z)-9-octadecen-1-amine 

Downstream Products

• 345637-71-0 (5-methyl-3-trifluoromethylpyrazol-1-yl)acetic acid 
• 866130-48-5 4-(3-methyl-5-trifluoromethyl-pyrazol-1-yl)-benzaldehyde 
• 299405-24-6 C₉H₁₁F₃N₂O₂ 
• 60061-68-9 4-bromo-5-methyl-3-(trifluoromethyl)-1H-pyrazole 
• 721402-02-4 4-bromo-1,5-dimethyl-3-(trifluoromethyl)-1H-pyrazole 
• 235106-12-4 4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazole 
• 79080-31-2 1,5-dimethyl-3-(trifluoromethyl)pyrazole 
• 1018325-07-9 1-(1-(4-chloro-3-methoxyphenyl)piperidin-4-yl)-2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)ethanone 
• 1105686-97-2 [η5-C5H4CH2C3HN2(CH3)(CF3)]Co[η4-(Ph4C)] 
• 1612287-74-7 3-((2-chloro-6-fluorophenyl)ethynyl)-5-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-amine 
• 1612287-75-8 N-(3-((2-chloro-6-fluorophenyl)ethynyl)-5-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)-2,2,2-trifluoroacetamide 
• 1612288-68-2 2-(2-chloro-6-fluorophenyl)-5-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)-1H-pyrrolo[2,3-b]pyridine 

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