122431-37-2

Basic information

• Product Name: 1-Methyl-3-(trifluoromethyl)-1H-pyrazol-5-ol
• Synonyms: 5-HYDROXY-1-METHYL-3-TRIFLUOROMETHYL-1H-PYRAZOLE;5-HYDROXY-1-METHYL-3-(TRIFLUOROMETHYL)PYRAZOLE;3-(TRIFLUOROMETHYL)-1-METHYL-1H-PYRAZOL-5-OL;1-METHYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOL-5-OL;5-Hydroxy-1-methyl-3-trifluoromethyl-1H-pyrazole, 99+%;2-METHYL-3-HYDROXY-5-TRIFLUOROMETHYLPYRAZOLE;1-Methyl-3-(trifluoromethyl)-1H-pyrazol-5-ol, 2-Methyl-5-(trifluoromethyl)-2H-pyrazol-3-ol;2-Methyl-5-trifluoromethyl-2H-pyrazol-3-ol
• CAS NO: 122431-37-2
• Molecular Formula: C₅H₅F₃N₂O
• Molecular Weight: 166.1
• EINECS: 1312995-182-4
• Product Categories: Building Blocks;Pyrazole
• Mol File: 122431-37-2.mol

Chemical Properties

• Melting Point: 177-179 °C
• Boiling Point: 106.4°Cat760mmHg
• Flash Point: 18.1°C
• Appearance: Light yellow/Crystalline Powder or Needles
• Density: 1.423g/cm³
• Vapor Pressure: 0.061mmHg at 25°C
• Refractive Index: 1.471
• PKA: 8.08±0.28(Predicted)
• CAS DataBase Reference: 1-Methyl-3-(trifluoromethyl)-1H-pyrazol-5-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methyl-3-(trifluoromethyl)-1H-pyrazol-5-ol(122431-37-2)
• EPA Substance Registry System: 1-Methyl-3-(trifluoromethyl)-1H-pyrazol-5-ol(122431-37-2)

Safety Data

• Hazard Codes: Xi,T
• Statements: 36/37/38-25
• Safety Statements: 24/25-45-26
• RIDADR: UN 2811 6.1 / PGIII
• HazardClass: IRRITANT
• Hazardous Substances Data: 122431-37-2(Hazardous Substances Data)

Usage

Chemical Properties

light yellow crystalline powder or needles

InChI:InChI=1/C5H5F3N2O/c1-10-4(11)2-3(9-10)5(6,7)8/h2,11H,1H3

Upstream product

• 372-31-6 ethyl 4,4,4-trifluoroacetoacetate 
• 60-34-4 methylhydrazine 
• 79424-03-6 ethyl 4,4,4-trifluoro-2-butynate 
• 40657-29-2 1,1,1-trifluoro-4,4-diethoxy-3-buten-2-one 
• 944546-18-3 ethyl-4,4,4-trifluoromethylacetoacetate 
• 19968-10-6 5-hydroxy-3-(trifluoromethyl)-1H-pyrazole 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 302-15-8 methylhydrazine sulfuric acid 
• 1522-43-6 ethyl 3-oxo-4,4,4-trifluorobutanoate enol 

Downstream Products

• 128455-62-9 5-chloro-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carbaldehyde 
• 211256-77-8 4-benzoyl-1-methyl-5-hydroxy-3-trifluoromethylpyrazole 
• 211256-74-5 4-bromo-5-benzoyloxy-1-methyl-3-trifluoromethylpyrazole 
• 211256-73-4 4-bromo-5-(4-methoxybenzoyl)oxy-1-methyl-3-trifluoromethylpyrazole 
• 211256-76-7 4-(4-methoxybenzoyl)-1-methyl-5-hydroxy-3-trifluoromethylpyrazole 
• 211256-75-6 4-(2,4-dichlorobenzoyl)-1-methyl-5-hydroxy-3-trifluoromethylpyrazole 
• 211256-72-3 4-bromo-5-(2,4-dichlorobenzoyl)oxy-1-methyl-3-trifluoromethylpyrazole 
• 179732-64-0 5-hydroxy-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxaldehyde 
• 481664-22-6 1-methyl-3-(trifluoromethyl)pyrazol-5-yl 2,4-dichlorobenzenesulfonate 
• 946409-57-0 5-benzyloxy-4-hydroxymethyl-1-methyl-3-trifluoromethylpyrazole 
• 1043921-56-7 C₁₂H₇ClF₃N₃O 
• 1279103-70-6 2-(5-Chloro-2-fluoro-phenyl)-5-(2-methyl-5-trifluoromethyl-2H-pyrazol-3-yl)-1H-indole 
• 1279103-76-2 3-Methyl-4-[5-(2-methyl-5-trifluoromethyl-2H-pyrazol-3-yl)-1H-indol-2-yl]-benzoic acid methyl ester 
• 1279106-68-1 2-(5-Chloro-2-fluoro-phenyl)-5-(2-methyl-5-trifluoromethyl-2H-pyrazol-3-yl)-indole-1-carboxylic acid ethyl ester 

Relevant articles and documents

Regiospecific synthesis of polyfluorinated heterocycles

A series of 10 heterocycles was obtained from the reaction of 1,1,1-trifluoro-4,4-diethoxy-3-buten-2-one and 1,1,1,2,2-pentafluoro-4, 4-diethoxy-3-penten-2-one with different dinucleofiles (hydrazine, methyl hydrazine, hydroxylamine and sodium cyanide). The pyrazoles, 4,5-dihydroisoxazoles and pyrrolidinones polyfluoroalkyl substituted were obtained in moderate to good yields under mild conditions.

New one-pot synthesis of 4-hydroxyimino-5-polyfluoroalkylpyrazol-3-ones, their structure and biological activity

[Figure not available: see fulltext.] We propose different methods for the synthesis of 4-hydroxyimino-5-polyfluoroalkylpyrazol-3-ones. The simplest and most convenient procedure relies on sequential one-pot treatment of polyfluoroalkyl-3-oxoesters with hydrazine and sodium nitrite in acetic acid. It was established that 4-hydroxyimino-5-polyfluoroalkylpyrazol-3-ones exist in solid state and in solutions as mixtures of Z,Е-isomers of the hydroxyimine tautomer. The synthesized compounds were characterized with respect to in vivo analgesic activity and acute toxicity.

Pyroxasulfone synthesis method

The invention provides a pyroxasulfone synthesis method. The method comprises the steps of: adopting a compound I as a starting raw material, carrying out cyclization reaction to synthesize an intermediate II, and carrying out chlorination reaction on the intermediate II under the action of a chlorination reagent to obtain an intermediate III; reacting the intermediate III with thiourea to obtaina hydrochloride intermediate IV, wherein the chlorination reagent is phosphorus pentachloride and/or phosphorus oxychloride; reacting the hydrochloride intermediate IV and a compound VI with formaldehyde to obtain an intermediate VII, carrying out difluoromethoxylation reaction on the intermediate VII to obtain an intermediate VIII, and oxidizing the intermediate VIII with hydrogen peroxide in thepresence of a catalyst to obtain pyroxasulfone IX, wherein the catalyst is sodium tungstate and acid. According to the method, the total yield is increased to 31-38%, the raw materials are simple andeasily available, the reaction process is simple and safe, the yield is high, and the method has certain significance for industrial production.

Design, synthesis, antifungal activity and 3D-QSAR study of novel pyrazole carboxamide and niacinamide derivatives containing benzimidazole moiety

A series of novel pyrazole carboxamide and niacinamide derivatives containing a benzimidazole moiety were designed and synthesized as antifungal candidate agents. All target compounds were characterized by FTIR, 1H NMR, 13C NMR, HRMS and elemental analysis techniques. The structure of compound T1 was further confirmed by single crystal X-ray diffraction analysis. The antifungal activities of the target compounds were evaluated in vitro against four phytopathogenic fungi (namely Botrytis cinerea, Rhizoctonia solani, Fusarium graminearum and Alternaria solani) by the mycelium growth inhibition method. The bioassay results indicated that some of the compounds exhibited good antifungal activity against B. cinerea at 100 μg ML?1 compared to other three fungi. In order to better explore the structure-activity relationship (SAR), the EC50 values of target compounds against B. cinerea were measured and assessed. Subsequently, a 3D quantitative structure-activity relationship (3D-QSAR) study was carried out using the comparative molecular field analysis (CoMFA) technique based on the inhibitory activities of tested compounds against B. cinerea. Molecular modelling results revealed fine predictive ability with cross-validated q2 and non-cross-validated r2 values of 0.578 and 0.850, respectively.

A new method for making pyrazole or pyrimidinone

The invention relates to the use of an amine compound in a method for producing a fluorinated or non-fluorinated 5- or 6-membered heterocyclic compound (preferably pyrazole or pyrimidinone) containingtwo nitrogen atoms in a ring system. The invention also relates to a method for producing a pyrazole or pyrimidinone, which may be fluorinated or may not be fluorinated (non-fluorinated). Each of thefluorinated pyrazole or fluorinated pyrimidinone is a very important structural unit for pharmaceutical and agricultural applications. For example, fungicides are strongly dependent on bifenapram, fluoxastrobin, flubenazolid, fluoxastrobin, pyraclostrobin, and pyracloprid, each with this fluorinated pyrazole as a key structural unit, and benflufenazole respectively, or diflufenacil and chlorfensulfazone (dimethachlor).

The competitive N1-, N2-, O- and C-methylation of 3-trifluoromethyl-1H-pyrazol-5-ol for synthesis of analgesic compounds

We have found selective conditions for methylation of 3-trifluoromethyl-1H-pyrazol-5-ol that allowed us to obtain mono-Me-substituted N1- and O-isomers as well N1,N2-, N1,O- and N2,O-disubstituted isomers. A tautomeric structure of the parent pyrazole and its Me-substituted derivatives was investigated using quantum-chemical calculations, X-ray diffraction analysis, IR and NMR spectroscopy. Besides, the quantum-chemical calculations were used to explain the methylation direction. An analgesic activity and acute toxicity of some synthesized compounds were evaluated in vivo experiments.

METHOD FOR PREPARATION OF 1-METHYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOL-5-OL

The invention discloses a method for the preparation of 1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-ol with high selectivity with respect to the content of the isomer 1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-ol, wherein ethyl 4,4,4-trifluoroacetoacetate is reacted with methyl hydrazine in the presence of 1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-ol: ethyl 4,4,4-trifluoroacetoacetate and methyl hydrazine are brought into contact in the presence of 1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-ol and are reacted in the presence of 1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-ol.

METHOD FOR PREPARATION OF 1-METHYL-3-(TRIFLUOROMETHYL)-1HPYRAZOL-5-OL

The invention discloses a method for the preparation of 1-methyl-3-(trifluoromethyl)-1H- pyrazol-5-ol with high selectivity with respect to the content of the isomer 1-methyl-5- (trifluoromethyl)-1H-pyrazol-3-ol.

PYRAZOLE DERIVATIVES AND RELATIVE USE FOR THE PREPARATION OF 1,3,4-THIADIAZOLES

The present invention relates to pyrazole derivatives having general formula (IV) and their use as intermediates for the preparation of 1, 3, 4-thiadiazoles having general formula (I) having herbicidal properties. The present invention also relates to the preparation process of said compounds having general formula (IV).

ANNELATED PYRROLES AND THEIR USE AS CRAC INHIBITORS

The invention relates to substituted bicyclic pyrroloheterocyclyl compounds of general formula (I), wherein A1 and A2 represent direct bond or C(=O), with the proviso that 0 or 1 of A1 and A2 represents C(=O); m and n independently denote 0, 1, 2 or 3, with the proviso that the sum [n + m] is 1, 2, 3 or 4; R1 denotes H, F, CI, Br, I, CN, CF3, CF2H, CFH2, CO2H, CO2R13, R13, OH. O-R13, NH2, N(H)R13, N(R13)2, R2 represents 0 to 4 substituents, each independently selected from F, CI, Br, CN. CF3, CF2H, CFH2, R13, OH, O-R13, NH2, N(H)R13 and N(R13)2; Ar1 represents phenyl or 5- or 6-membered heteroaryl, in each case unsubstituted or substituted with one, two, three or four substituents, independently selected from F, CI, Br, CN, CF3. CF2H, CFH2, R13 and O- R13; or C3-6-cycloalkyl or 3 to 7 membered heterocycloalkyl, in each case unsubstituted or mono- or polysubstituted; Ar2 represents phenyl or 5- or 6-membered heteroaryl, wherein said phenyl or said heteroaryl may be unsubstituted or mono- or polysubstituted and may be condensed with a 4-, 5-, 6-or 7- membered ring, being carbocyclic or heterocyclic, wherein said condensed ring may be saturated, partially unsaturated or aromatic and may be unsubstituted or mono- or polysubstituted; useful as ICRAC inhibitors, to pharmaceutical compositions containing these compounds and to these compounds for the use in the treatment and/or prophylaxis of diseases and/or disorders, in particular inflammatory diseases and/or inflammatory disorders.