128455-62-9

Basic information

• Product Name: 5-CHLORO-1-METHYL-3-(TRIFLUOROMETHYL)PYRAZOLE-4-CARBOXALDEHYDE
• Synonyms: TIMTEC-BB SBB000527;BUTTPARK 46\18-83;AKOS B029556;5-CHLORO-1-METHYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBALDEHYDE;5-CHLORO-1-METHYL-3-(TRIFLUOROMETHYL)PYRAZOLE-4-CARBOXALDEHYDE;5-Chloro-1-methyl-3-(trifluoromethyl)pyrazole-4-carboxyaldehyde;3-trifluoromethyl-1-methyl-1H-5-chloropyrazole-4-carbaldehyde;5-Chloro-4-formyl-1-methyl-3-(trifluoromethyl)-1H-pyrazole
• CAS NO: 128455-62-9
• Molecular Formula: C₆H₄ClF₃N₂O
• Molecular Weight: 212.56
• EINECS: 1312995-182-4
• Product Categories: Pyrazoles & Triazoles;Aldehydes;Pyrazoles & Triazoles;Building Blocks;Pyrazole
• Mol File: 128455-62-9.mol

Chemical Properties

• Melting Point: 42-44°C
• Boiling Point: 239.6°C at 760 mmHg
• Flash Point: 98.7°C
• Appearance: /
• Density: 1.56g/cm³
• Vapor Pressure: 0.0396mmHg at 25°C
• Refractive Index: 1.501
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -4.03±0.10(Predicted)
• CAS DataBase Reference: 5-CHLORO-1-METHYL-3-(TRIFLUOROMETHYL)PYRAZOLE-4-CARBOXALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLORO-1-METHYL-3-(TRIFLUOROMETHYL)PYRAZOLE-4-CARBOXALDEHYDE(128455-62-9)
• EPA Substance Registry System: 5-CHLORO-1-METHYL-3-(TRIFLUOROMETHYL)PYRAZOLE-4-CARBOXALDEHYDE(128455-62-9)

Safety Data

• Hazard Codes: Xi
• Statements: R36/37/38:Irritating to eyes, respiratory system and skin.
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S37/39:Wear suitable g
• Hazardous Substances Data: 128455-62-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-CHLORO-1-METHYL-3-(TRIFLUOROMETHYL)PYRAZOLE-4-CARBOXALDEHYDE is used as a key intermediate for the synthesis of bioactive molecules, contributing to the development of new pharmaceuticals with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 5-CHLORO-1-METHYL-3-(TRIFLUOROMETHYL)PYRAZOLE-4-CARBOXALDEHYDE is utilized as a precursor in the production of compounds with pesticidal and herbicidal properties, aiding in the creation of effective solutions for crop protection and management.

InChI:InChI=1/C6H4ClF3N2O/c1-12-5(7)3(2-13)4(11-12)6(8,9)10/h2H,1H3

Upstream product

• 122431-37-2 2-methyl-5-trifluoromethyl-2H-pyrazol-3-ol 
• 68-12-2 N,N-dimethyl-formamide 
• 75-03-6 ethyl iodide 
• 1481-02-3 2,4-dihydro-2-methyl-5-trifluoromethyl-3H-pyrazol-3-one 
• 356759-12-1 2-methyl-5-(trifluoromethyl)-1,2-dihydro-3H-pyrazol-3-one 

Downstream Products

• 321533-90-8 5-(2-chlorobenzylsulfanyl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxaldehyde 
• 321553-53-1 5-(4-tert-butyl-benzylsulfanyl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carbaldehyde 
• 769171-48-4 C₁₈H₁₃F₃N₂O₄ 
• 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 
• 929634-33-3 5-[5-(4-chloro-benzylsulfanyl)-1-methyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylene]-2-thioxo-thiazolidin-4-one 
• 321533-70-4 5-(4-chloro-phenylsulfanyl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carbaldehyde 
• 929634-62-8 5-benzylsulfanyl-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carbaldehyde 
• 321533-77-1 1-methyl-5-phenylsulfanyl-3-trifluoromethyl-1H-pyrazole-4-carbaldehyde 
• 128455-63-0 5-chloro-1-methyl-3-trifluoromethylpyrazole-4-carboxylic acid 

Relevant articles and documents

Novel 5-chloro-pyrazole derivatives containing a phenylhydrazone moiety as potent antifungal agents: synthesis, crystal structure, biological evaluation and a 3D-QSAR study

Based on the active substructure combination principle, twenty-four novel 5-chloro-pyrazole derivatives containing a phenylhydrazone moiety were designed, synthesized, and evaluated for their antifungal activity. Their structures were confirmed using 1H NMR, 13C NMR, and HR-MS spectra. The single-crystal structure of compound 8a was analyzed emphatically using X-ray diffraction. The antifungal activities against Fusarium graminearum, Botrytis cinerea, and Rhizoctonia solani were evaluated in vitro. The results of the bioassays revealed that most of the target compounds showed obvious fungicidal activity. Strikingly, the compound 7c exhibited the most potent activity with EC50 values of 0.74, 0.68, and 0.85 μg mL?1 against the above three plant pathogenic fungi, respectively. The compounds 7c, 8d, and 8g showed significant bioactivity against R. solani with EC50 values of 0.85, 0.25, and 0.96 μg mL?1, respectively. In addition, CoMFA and CoMSIA molecular modeling was performed for a 3D-QSAR study, and presented a good predictive ability with q2 values of 0.575 and 0.667, and r2 values of 0.961 and 0.962, respectively. The results provide useful information for guiding the design and synthesis of novel potent pyrazole derivatives with good antifungal activity.

Isoxazoline derivative and application thereof in agriculture

The invention provides an isoxazoline derivative and application of the isoxazoline derivative in agriculture. Specifically, the invention provides a compound as shown in a formula (I) or a stereoisomer, nitrogen oxide or salt of the compound as shown in the formula (I), and a preparation method thereof. In the formula (I), R1, R2, R3, R4, n, R5, R6, R7, R8 and Acy are as defined in the invention.Further, the invention provides compositions containing these compounds and use thereof in agriculture, particularly as herbicidal active ingredients for controlling unwanted plants.

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.

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).

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.

5-((1H-Pyrazol-4-yl)methylene)-2-thioxothiazolidin-4-one inhibitors of ADAMTS-5

A series of 5-((1H-pyrazol-4-yl)methylene)-2-thioxothiazolidin-4-one inhibitors of ADAMTS-5 (aggrecanase-2) is described. These compounds show μM functional inhibition of ADAMTS-5, and represent a new class of agents with the potential of inhibiting degradation of aggrecan, a major component of cartilage which is lost in osteoporosis. Compound 12 is noteworthy in that it has an ADAMTS-5 IC50: 1.1 μM and shows >40-fold functional selectivity over ADAMTS-4 (aggrecanase-1).

NOVEL HERBICIDES

Compounds of formula (I) wherein the substituents are defined as in claim 1, are suitable for use as herbicides. Also claimed is the intermediate (II) wherein R1 is chloro, R2 is hydrogen and XA is methylsulfonate, three p