947-95-5

Basic information

• Product Name: 5-CHLORO-3-METHYL-1-PHENYL-1H-PYRAZOLE-4-CARBALDEHYDE
• Synonyms: AKOS BBS-00001388;AKOS B018718;5-CHLORO-3-METHYL-1-PHENYL-1H-PYRAZOLE-4-CARBALDEHYDE;5-CHLORO-3-METHYL-1-PHENYL-4-PYRAZOLECARBOXALDEHYDE;5-CHLORO-3-METHYL-1-PHENYL PYRAZOLE-4-ALDEHYDE;5-CHLORO-3-METHYL-1-PHENYLPYRAZOLE-4-CARBALDEHYDE;5-CHLORO-3-METHYL-1-PHENYLPYRAZOLE-4-CARBOXALDEHYDE;5-CHLORO-4-FORMYL-3-METHYL-1-PHENYLPYRAZOLE
• CAS NO: 947-95-5
• Molecular Formula: C₁₁H₉ClN₂O
• Molecular Weight: 220.65
• Product Categories: Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyrazoles;PyrazolesHeterocyclic Building Blocks
• Mol File: 947-95-5.mol
• Article Data: 92

Chemical Properties

• Melting Point: 145-148 °C(lit.)
• Boiling Point: 356.1 °C at 760 mmHg
• Flash Point: 169.2 °C
• Appearance: light yellow to yellow flakes or needles
• Density: 1.26
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -3.81±0.10(Predicted)
• CAS DataBase Reference: 5-CHLORO-3-METHYL-1-PHENYL-1H-PYRAZOLE-4-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLORO-3-METHYL-1-PHENYL-1H-PYRAZOLE-4-CARBALDEHYDE(947-95-5)
• EPA Substance Registry System: 5-CHLORO-3-METHYL-1-PHENYL-1H-PYRAZOLE-4-CARBALDEHYDE(947-95-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 947-95-5(Hazardous Substances Data)

Usage

Description

5-Chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde is an organic compound that serves as a key intermediate in the synthesis of various pharmaceutically active molecules. It is characterized by the presence of a chloro, methyl, and phenyl group attached to a pyrazole ring, with a carbaldehyde functional group at the 4-position.

Uses

Used in Pharmaceutical Synthesis:
5-Chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde is used as a starting material for the synthesis of various pyrazole derivatives with potential pharmacological applications. These derivatives have been evaluated for their analgesic and anti-inflammatory properties, making them valuable in the development of new drugs for pain relief and inflammation management.
Used in the Synthesis of Hydrazones:
5-CHLORO-3-METHYL-1-PHENYL-1H-PYRAZOLE-4-CARBALDEHYDE is utilized in the synthesis of 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carboxaldehyde hydrazone, which is a key intermediate in the preparation of other biologically active molecules.
Used in the Synthesis of Thiosemicarbazones:
5-Chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde is also used in the synthesis of N1-((5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene)thiosemicarbazone, a class of compounds known for their diverse biological activities, including antimicrobial, antiviral, and anticancer properties.
Used in the Synthesis of Substituted Hydrazides:
Furthermore, this compound is employed in the synthesis of N′-[(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene] 2/4-substituted hydrazides, which are of interest in medicinal chemistry due to their potential therapeutic applications.

Upstream product

• 1131-17-5 5-chloro-3-methyl-1-phenyl-1H-pyrazole 
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• 19735-89-8 3-methyl-1-phenylpyrazolin-5(4H)-one 
• 93-61-8 N-methyl-N-phenylformamide 
• 100-63-0 phenylhydrazine 
• 13292-56-3 5-methyl-2-phenylpyrazolidin-3-one 
• 1128-54-7 3-methyl-1-phenyl-1H-pyrazole 
• 100-97-0 hexamethylenetetramine 
• 99068-19-6 C₁₀H₁₂N₂O₂ 
• 6078-46-2 ethyl 3-(2-phenylhydrazono)butanoate 
• 59-88-1 phenylhydrazine hydrochloride 
• 62-53-3 aniline 

Downstream Products

• 109576-78-5 3-{[3-Methyl-1-phenyl-5-selenoxo-1,5-dihydro-pyrazol-(4Z)-ylidenemethyl]-amino}-benzoic acid methyl ester 
• 104753-35-7 4-{[3-Methyl-1-phenyl-5-thioxo-1,5-dihydro-pyrazol-(4Z)-ylidenemethyl]-amino}-benzoic acid ethyl ester 
• 160348-48-1 3-methyl-5-(3-methylbut-2-enylsulfanyl)-1-phenyl-1H-pyrazole-4-carbaldehyde 
• 160348-57-2 5-(but-3-enyloxy)-3-methyl-1-phenylpyrazole-4-carbaldehyde 
• 160348-49-2 5-furfurylsulfanyl-3-methyl-1-phenylpyrazole-4-carbaldehyde 
• 104753-33-5 4-[1-(3-Methoxy-phenylamino)-meth-(Z)-ylidene]-5-methyl-2-phenyl-2,4-dihydro-pyrazole-3-thione 
• 104753-30-2 5-Methyl-2-phenyl-4-[1-p-tolylamino-meth-(Z)-ylidene]-2,4-dihydro-pyrazole-3-thione 
• 109576-82-1 5-Methyl-2-phenyl-4-[1-p-tolylamino-meth-(Z)-ylidene]-2,4-dihydro-pyrazole-3-selone 
• 109576-79-6 4-[1-(4-Chloro-phenylamino)-meth-(Z)-ylidene]-5-methyl-2-phenyl-2,4-dihydro-pyrazole-3-selone 
• 104753-29-9 4-[1-(4-Methoxy-phenylamino)-meth-(Z)-ylidene]-5-methyl-2-phenyl-2,4-dihydro-pyrazole-3-thione 
• 109604-14-0 4-[1-(4-Methoxy-phenylamino)-meth-(Z)-ylidene]-5-methyl-2-phenyl-2,4-dihydro-pyrazole-3-selone 
• 160348-55-0 3-methyl-1-phenyl-5-(prop-2-ynyloxy)pyrazole-4-carbaldehyde 
• 104753-28-8 4-[1-(4-Dimethylamino-phenylamino)-meth-(Z)-ylidene]-5-methyl-2-phenyl-2,4-dihydro-pyrazole-3-thione 
• 109576-83-2 4-[1-(4-Dimethylamino-phenylamino)-meth-(Z)-ylidene]-5-methyl-2-phenyl-2,4-dihydro-pyrazole-3-selone 

Relevant articles and documents

Synthesis and biological evaluation of novel triazole substituted pyrazolyl-methylenehydrazinyl-5-arylidene thiazolidinone derivatives as antibacterial and cytotoxic agents

Novel triazole substituted pyrazolyl-methylenehydrazinyl-5-arylidene thiazolidinone derivatives 6a–n and 7a–l were synthesized and characterized by Fourier transform infrared, 1H and 13C nuclear magnetic resonance, mass spectrometry and elemental (CHN) analysis. The in vitro antibacterial (6a–n and 7a–l) and cytotoxic (6a–n) activities were evaluated for these compounds. The results revealed that the compounds 6b, 6i, 6k, 7b, 7h displayed good antibacterial activity. The compounds 6c (IC50?=?5.4?μM), 6l (IC50?=?6.3?μM) and 6f (IC50?=?9.85?μM) were effective for inhibition of human breast cancer cell line MCF-7. Similarly, the compounds 6b (IC50?=?8.7?μM) and 6c (IC50?=?9.06?μM) were shown to have effective inhibition on human cervical cancer cell line Hela.

Bipyrazole-based palladium(II) complexes as DNA intercalator and artificial metallonuclease

Abstract: Substituted 3′-methyl-1′,2-diphenyl-3,4-dihydro-1′H,2H-3,4′-bipyrazole and their square planar palladium(II) complexes of type [Pd(4n)Cl2], where 4n = bipyrazole-based ligands, have been synthesized. The compounds have been characterized by various techniques like elemental analysis, mass, absorption, IR, 1H NMR and 13C NMR spectroscopy. The complexes have been further analyzed by thermogravimetric analysis (TGA), conductance measurement and energy-dispersive X-ray spectroscopy (EDX). Interaction between compounds and herring sperm DNA has been studied by absorption titration, viscosity measurement, ethidium bromide displacement titration, and molecular docking study. The binding strength between compounds and DNA has been checked in terms of Kb, Ksv, and Kf values; while spontaneity of interaction has been checked by evaluating thermodynamic parameters like Gibb’s free energy, enthalpy change (?H°) and entropy change (?S°). The plasmid cleavage efficacy of complexes has been evaluated by gel electrophoresis technique. The minimum inhibitory concentration of compounds has been evaluated against pathogens such as Staphylococcus aureus, Escherichia coli, B. subtilis, S. marcescens and Pseudomonas aeruginosa. The in vivo and in vitro cytotoxic activity has been performed using cell viability assay and brine shrimp lethality bioassay. Graphical abstract: [Figure not available: see fulltext.].

Microwave assisted one-pot synthetic route to imidazo[1,2-: A] pyrimidine derivatives of imidazo/triazole clubbed pyrazole and their pharmacological screening

An efficient synthesis of imidazo[1,2-a]pyrimidine derivatives of pyrazole in excellent yield over a short reaction time based on a microwave-assisted, one-pot three-component condensation reaction of pyrazole aldehyde clubbed with imidazole 4 and triazole 5 nuclei, (substituted-phenyl/hetero-aryl)ethanones 6(a-g), and 2-amino benzimidazole 7 in the presence of the strong base KOH is described. All the compounds were screened for their preliminary in vitro antimicrobial, antituberculosis and antimalarial activities against a panel of pathogenic strains. The majority of the compounds exhibited excellent inhibitory action against S. typhi, S. pneumoniae, B. subtilis, and C. tetani. Some of the compounds showed good antifungal activity and moderate antituberculosis activity as compared to first line drugs. Two of the compounds 8b and 9b exhibited excellent antimalarial activity against P. falciparum strains.

Design, synthesis, antibacterial evaluation and molecular docking studies of novel pyrazole/1,2,4-oxadiazole conjugate ester derivatives

The development of new antimicrobial drugs is most needed due to rapid growth in global antimicrobial resistance. Thus, in this context, a series of novel pyrazole/1,2,4-oxadiazole conjugate ester derivatives (7a–j) was synthesized. All the derivatives we

Synthesis of Selenopyrano[2,3- c ]pyrazol-4(1 H)-ones and Their C-H Activation

We disclose the synthesis of selenopyrano[2,3- c ]pyrazol-4(1 H)-ones and their aryl derivatives for the first time by using selenopyran ring formation via an in situ-generated selenide that reacts directly with α-halo-β-ynone-bearing substituted pyrazole