128455-63-0

Basic information

• Product Name: 5-CHLORO-1-METHYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID
• Synonyms: 5-Chloro-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylicacid97%;5-Chloro-1-methyl-3-(trifluoromethyl);BUTTPARK 99\18-36;5-CHLORO-1-METHYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID;RARECHEM AL BO 1764;4-Carboxy-5-chloro-1-methyl-3-(trifluoromethyl)-1H-pyrazole
• CAS NO: 128455-63-0
• Molecular Formula: C₆H₄ClF₃N₂O₂
• Molecular Weight: 228.56
• EINECS: 1312995-182-4
• Product Categories: Heterocyclic Building Blocks;New Products for Chemical Synthesis;Pyrazoles;Carboxylic Acids;Pyrazoles & Triazoles;Carboxylic Acids;Pyrazoles & Triazoles;Building Blocks;Pyrazole;C6;Chemical Synthesis
• Mol File: 128455-63-0.mol

Chemical Properties

• Melting Point: 201 °C
• Boiling Point: 284.4 °C at 760 mmHg
• Flash Point: 125.8 °C
• Appearance: /
• Density: 1.71 g/cm³
• Vapor Pressure: 0.0014mmHg at 25°C
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 1.77±0.50(Predicted)
• CAS DataBase Reference: 5-CHLORO-1-METHYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLORO-1-METHYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID(128455-63-0)
• EPA Substance Registry System: 5-CHLORO-1-METHYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID(128455-63-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26
• HazardClass: IRRITANT
• Hazardous Substances Data: 128455-63-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
5-CHLORO-1-METHYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID is used as a building block for the synthesis of pharmaceuticals, contributing to the development of new drugs with improved bioavailability and metabolic stability due to the presence of the trifluoromethyl group.
Used in Agrochemical Synthesis:
In the agrochemical industry, 5-CHLORO-1-METHYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID serves as a key component in the creation of agrochemicals, potentially enhancing the effectiveness and stability of these compounds for agricultural applications.
Used as a Reagent in Organic Synthesis:
5-CHLORO-1-METHYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID is utilized as a reagent in organic synthesis to introduce the pyrazole-4-carboxylic acid motif into molecules, allowing for the creation of a variety of chemical entities with specific properties and applications.

InChI:InChI=1/C6H4ClF3N2O2/c1-12-4(7)2(5(13)14)3(11-12)6(8,9)10/h1H3,(H,13,14)/p-1

Upstream product

• 128455-62-9 5-chloro-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carbaldehyde 
• 1481-02-3 2,4-dihydro-2-methyl-5-trifluoromethyl-3H-pyrazol-3-one 
• 122431-37-2 2-methyl-5-trifluoromethyl-2H-pyrazol-3-ol 

Downstream Products

• 944546-10-5 5-(2-chlorobenzylsulfanyl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid 
• 1300734-66-0 bis(2-methoxyethyl)((5-chloro-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamido)(phenyl)methyl)phosphonate 
• 1300734-62-6 diethyl((5-chloro-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamido)(phenyl)methyl)phosphonate 
• 1300734-63-7 dipropyl((5-chloro-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamido)(phenyl)methyl)phosphonate 
• 1300734-64-8 diisopropyl ((5-chloro-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamido)(phenyl)methyl)phosphonate 
• 1300734-65-9 dibutyl((5-chloro-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-arboxamido)(phenyl)methyl)phosphonate 

Relevant articles and documents

Synthesis of novel EP4 antagonists and their use in cancer and inflammation

The present invention relates to a compound capable of effectively antagonizing EP4, which is a compound represented by formula I, or a tautomer, a stereoisomer, a hydrate, a solvate, a pharmaceutically-acceptable salt or a prodrug of the compound represented by formula I. R1 is selected from -CH3, -CHF2, and -CF3; R2 is selected from C2-C6 alkyl, C3-C6 cycloalkyl, halogenated C2-C6 alkyl, and halogenated C3-C6 cycloalkyl; R3 is selected from hydrogen, halogen, C1-C2 alkyl, and fluorinated C1-C2 alkyl; R4 is selected from hydrogen, halogen, C1-C6 alkyl, C1-C6 alkoxy, halogenated C1-C6 alkyl, and halogenated C1-C6 alkoxy.

Expedient discovery for novel antifungal leads targeting succinate dehydrogenase: Pyrazole-4-formylhydrazide derivatives bearing a diphenyl ether fragment

The pyrazole-4-carboxamide scaffold containing a flexible amide chain has emerged as the molecular skeleton of highly efficient agricultural fungicides targeting succinate dehydrogenase (SDH). Based on the above vital structural features of succinate dehydrogenase inhibitors (SDHI), three types of novel pyrazole-4-formylhydrazine derivatives bearing a diphenyl ether moiety were rationally conceived under the guidance of a virtual docking comparison between bioactive molecules and SDH. Consistent with the virtual verification results of a molecular docking comparison, the in vitro antifungal bioassays indicated that the skeleton structure of title compounds should be optimized as an N′-(4-phenoxyphenyl)-1H-pyrazole-4-carbohydrazide scaffold. Strikingly, N′-(4-phenoxyphenyl)-1H-pyrazole-4-carbohydrazide derivatives 11o against Rhizoctonia solani, 11m against Fusarium graminearum, and 11g against Botrytis cinerea exhibited excellent antifungal effects, with corresponding EC50 values of 0.14, 0.27, and 0.52 μg/mL, which were obviously better than carbendazim against R. solani (0.34 μg/mL) and F. graminearum (0.57 μg/mL) as well as penthiopyrad against B. cinerea (0.83 μg/mL). The relative studies on an in vivo bioassay against R. solani, bioactive evaluation against SDH, and molecular docking were further explored to ascertain the practical value of compound 11o as a potential fungicide targeting SDH. The present work provided a non-negligible complement for the structural optimization of antifungal leads targeting SDH.

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.

Containing substituted 1, 3, 4-thiadiazole sulfide pyrazole amide and pyrazole imine derivatives and preparation method and application

The invention discloses pyrazole amide and pyrazole imine derivatives containing substituted 1, 3, 4-thiadiazole thioether as well as a preparation method and an application of the derivatives. The compounds have the structures as shown in formulae (I) and (II). The preparation method comprises the following steps: by taking substituted hydrazine as an initial raw material, carrying out closed loop, chlorine formylation, oxidation and chloro reaction to obtain pyrazole acyl chloride; carrying out a reaction on 2-amino-5-mercapto-1, 3, 4-thiadiazole and substituted benzyl chloride to obtain 2-amino-5-substituted 1, 3, 4-thiadiazole thioether; and then, carrying out a substitution reaction on 2-amino-5-substituted 1, 3, 4-thiadiazole thioether and substituted pyrazole acyl chloride to obtain the pyrazole amide compound (I) containing substituted 1, 3, 4-thiadiazole thioether; by taking substituted hydrazine as an initial raw material, carrying out closed loop and chlorine formylation to obtain pyrazole aldehyde; carrying out an additive elimination reaction on pyrazole aldehyde and 2-amino-5-mercapto-1, 3, 4-thiadiazole under a backflow condition of anhydrous ethanol to obtain 2-substituted pyrazole imidogen-5-mercapto-1, 3, 4-thiadiazole; and then carrying out a reaction on 2-substituted pyrazole imidogen-5-mercapto-1, 3, 4-thiadiazole and substituted benzyl chloride to generate the pyrazole imine compound (II) containing substituted 1, 3, 4-thiadiazole thioether. The compounds disclosed by the invention have a good inhibiting effect on tobacco mosaic virus and can be used for preparing anti-plant virus drugs.

Synthesis and antiviral activity of novel pyrazole amides containing α-aminophosphonate moiety

A series of novel pyrazole amides J1-J15 containing an α-aminophosphonate moiety were synthesized and subsequently characterized by spectral (IR, 1H-, 13C-, 31P-, and 19F-NMR) data and elemental analysis. The racemic sample of J1 was further separated into its enantiomers under normal-phase condition on two immobilized polysaccharide-based chiral stationary phases (Chiralpak IA and Chiralpak IC). The synthesized compounds revealed certain degree of antiviral activity in the bioassay. The title compounds (J 3, J10, and J12) showed some curative activities (39.9%, 41.8%, 50.1%, respectively) against tobacco mosaic virus at 0.5 mg/mL.

TREATMENT OF INFLAMMATION AND RELATED DISORDERS BY ACTIVATION OF THE UNFOLDED PROTEIN RESPONSE

The present invention is directed to a novel method for the treatment of diseases by activating the unfolded protein response (UPR), or of inhibiting the expression of the inducible isoform of the nitric oxide synthase (iNOS) enzyme, or both. New methylpyrazole compounds which activate the UPR, downregulate iNOS, and reduce inflammatory markers are disclose herein, as are compositions comprising said compounds and their applications as pharmaceuticals for the treatment of disease.

Processes for the preparation of pyrazole compounds

A process (1) for the preparation of 4-cyanoacetylpyrazoles of the general formula (I) wherein R1 is C1-6 alkyl, R2 is C1-6 alkyl or C1-6 haloalkyl, and X is hydrogen or C1-6 alkyl which comprises using a pyrazolecarboxylic acid halide and a cyanoacetate ester; a process (2) for the preparation of the same which comprises using a pyrazolecarboxylic acid and a cyanoacetate ester; a process (3) for the preparation of the same which comprises using a pyrazolecarbonitrile; and a process (4) for the preparation of the same which comprises using a haloacetylpyrazole. Furthermore, an industrially advantageous process for preparing pyrazolecarboxylic acids useful as intermediates in the above processes.

Etylene derivatives and pesticides containing said derivatives

Ethylene derivatives of formula (I): where Q is an unsubstituted or substituted phenyl or heterocyclic group, especially a 4-thiazolyl, 1- or 3-pyrazolyl, 1,3-oxazol-4-yl, phenyl or pyridyl group; E is a substituent such as a cyano group; A is a substituent such as a 4-pyrazolyl or thiazolyl group; and B is a substituent such as an alkylcarbonyl group. Agricultural chemicals and agents for preventing the attachment of aquatic organisms containing one or more such ethylene derivatives.

Synthesis and 13C NMR of (Trifluoromethyl)hydroxypyrazoles

Reaction of ethyl 4,4,4-trifluoroacetoacetate with methylhydrazine produced not only the previously reported 5-hydroxy-3-(trifluoromethyl)pyrazole 1 but also its unknown isomer the 3-hydroxy-5-(trifluoromethyl)pyrazole 4.The structure assignments are established based on 13C nmr spectra.Compound 1 was converted to 5-chloro-3-(trifluoromethyl)pyrazolecarboxylic acid 3 in two steps.