3-(4-methylphenyl)-5-(trifluoromethyl)-1H-pyrazole

Base Information

• Chemical Name: 3-(4-methylphenyl)-5-(trifluoromethyl)-1H-pyrazole
• CAS No.: 219986-64-8
• Molecular Formula: C₁₁H₉F₃N₂
• Molecular Weight: 226.201
• European Community (EC) Number: 646-564-7
• UNII: G5K9F2B76J
• DSSTox Substance ID: DTXSID10400173
• Nikkaji Number: J1.026.884B,J3.201.781I
• Wikidata: Q82203017
• Mol file: 219986-64-8.mol

Synonyms:219986-64-8;3-(4-methylphenyl)-5-(trifluoromethyl)-1H-pyrazole;3-(Trifluoromethyl)-5-p-tolyl-1H-pyrazole;3-(4-methylphenyl)-5-(trifluoromethyl)pyrazole;3-(p-Tolyl)-5-(trifluoromethyl)-1H-pyrazole;26974-15-2;948293-46-7;5-(p-Tolyl)-3-(trifluoromethyl)-1H-pyrazole;MFCD03934062;G5K9F2B76J;Celecoxib N-des(benzenesulfonamide);5-(4-methylphenyl)-3-trifluoromethyl-1h-pyrazole;5-(4-Methylphenyl)-3-(trifluoromethyl)-1H-pyrazole;3-trifluoromethyl-5-(p-tolyl)-1h-pyrazole;1H-Pyrazole, 5-(4-methylphenyl)-3-(trifluoromethyl)-;1H-Pyrazole, 3-(4-methylphenyl)-5-(trifluoromethyl)-;Celecoxib Impurity 11;UNII-G5K9F2B76J;SCHEMBL5352040;SCHEMBL21614027;DTXSID10400173;BCP33838;MFCD07779618;AKOS015950510;AKOS017343861;BS-42081;SY005287;3-p-Tolyl-5-(trifluoromethyl)-1H-pyrazole;3-trifluoromethyl-5-(p-tolyl)-1h pyrazole;5-p-tolyl-3-(trifluoromethyl)-1H-pyrazole;FT-0711262;FT-0738803;3-(Trifluoromethyl)-5-(p-Tolyl)-1H-Pyrazole;D86584;W18889;A878822;J-016639;des-benzenesulfonamide impurity;5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazole

Chemical Property of 3-(4-methylphenyl)-5-(trifluoromethyl)-1H-pyrazole

Chemical Property:

• Vapor Pressure: 0.000133mmHg at 25°C
• Melting Point: 155.3-156.8 °C
• Boiling Point: 344.2oC at 760 mmHg
• PKA: 10.08±0.10(Predicted)
• Flash Point: 162oC
• PSA: 28.68000
• Density: 1.284g/cm3
• LogP: 3.40390
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 226.07178278
• Heavy Atom Count: 16
• Complexity: 234

Purity/Quality:

98%min ^*data from raw suppliers

3-Trifluoromethyl-5-(p-tolyl)-1H-pyrazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C2=NNC(=C2)C(F)(F)F
• Uses: 3-Trifluoromethyl-5-(p-tolyl)-1H-pyrazole is an impurity of cyclooxygenase-2 (COX-2) inhibitor Celecoxib (C251000).

Technology Process of 3-(4-methylphenyl)-5-(trifluoromethyl)-1H-pyrazole

There total 4 articles about 3-(4-methylphenyl)-5-(trifluoromethyl)-1H-pyrazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

5-hydroxy-3-p-tolyl-5-trifluoromethyl-4,5-dihydro-pyrazole-1-carbothioic acid amide (219986-59-1) → 3-p-tolyl-5-(trifluormethyl)-1H-pyrazole (219986-64-8,948293-46-7)

Guidance literature:

With sulfuric acid; for 4h; Heating;

DOI:10.1016/S0022-1139(98)00242-5

Reference yield:

4-methyl-benzoyl chloride (874-60-2) → 3-p-tolyl-5-(trifluormethyl)-1H-pyrazole (219986-64-8,948293-46-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi; N,N,N',N'-tetramethylethylenediamine / tetrahydrofuran; hexane / -78 °C

1.2: 79 percent / tetrahydrofuran; hexane / 0.25 h / -78 °C

2.1: 88 percent / hydrazine monohydrate / ethanol / Heating

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; hydrazine hydrate; In tetrahydrofuran; ethanol; hexane;

DOI:10.1016/j.tetlet.2007.03.105

Reference yield:

1,1,1-trifluoro-4-methoxy-4-(4-methylphenyl)-3-buten-2-one (187812-31-3) → 3-p-tolyl-5-(trifluormethyl)-1H-pyrazole (219986-64-8,948293-46-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / methanol / 20 h / 40 - 45 °C

2: 75 percent / H₂SO₄ / 4 h / Heating

With sulfuric acid; In methanol;

DOI:10.1016/S0022-1139(98)00242-5

upstream raw materials:

5-hydroxy-3-p-tolyl-5-trifluoromethyl-4,5-dihydro-pyrazole-1-carbothioic acid amide

3-cyano-6-(4-tolyl)-4-trifluoromethyl-2(1H)-pyridone

4-methyl-benzoyl chloride

1,1,1-trifluoro-4-methoxy-4-(4-methylphenyl)-3-buten-2-one

Refernces

• 1、 Hanamoto, Takeshi,Anno, Ryoko,Yamada, Kenji,Ryu, Kousuke. "Facile synthesis of α-functionalized vinyl sulfides bearing β-trifluoromethyl group: a highly potential CF3-containing building blocks". . p. 3727 - 3730. Retrieved 2008/02/09.