14580-22-4

Basic information

• Product Name: 1-(2-Chlorophenyl)-3-methyl-2-pyrazolin-5-one
• Synonyms: LABOTEST-BB LT00452413;1-(O-CHLOROPHENYL)-3-METHYL-2-PYRAZOLINE-5-ONE;1-(O-CHLOROPHENYL)-3-METHYL-5-PYRAZOLONE;2-(2-chlorophenyl)-2,4-dihydro-5-methyl-3h-pyrazol-3-one;1-(2-CHLOROPHENYL)-3-METHYL-2-PYRAZOLIN-5-ONE;1-(2'-CHLOROPHENYL)-3-METHYL-5-PYRAZOLONE;1-(2-CHLOROPHENYL)-3-METHYL-5-PYRAZOLONE;1-(2-CHLOROPHENYL)-3-METHYL-5-PYRAZOLONE HYDRATE
• CAS NO: 14580-22-4
• Molecular Formula: C₁₀H₉ClN₂O
• Molecular Weight: 208.64
• EINECS: 238-623-7
• Product Categories: Intermediates of Dyes and Pigments;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyrazoles;PyrazolesHeterocyclic Building Blocks;API Intermediate
• Mol File: 14580-22-4.mol
• Article Data: 10

Chemical Properties

• Melting Point: 193-197 °C(lit.)
• Boiling Point: 361.6 °C at 760 mmHg
• Flash Point: 172.5 °C
• Appearance: /
• Density: 1.32 g/cm³
• Vapor Pressure: 2.04E-05mmHg at 25°C
• Refractive Index: 1.625
• PKA: 2.05±0.50(Predicted)
• CAS DataBase Reference: 1-(2-Chlorophenyl)-3-methyl-2-pyrazolin-5-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-Chlorophenyl)-3-methyl-2-pyrazolin-5-one(14580-22-4)
• EPA Substance Registry System: 1-(2-Chlorophenyl)-3-methyl-2-pyrazolin-5-one(14580-22-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• WGK Germany: 1
• Hazardous Substances Data: 14580-22-4(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow crystalline powder

Uses

1-(2-Chlorophenyl)-3-methyl-2-pyrazolin-5-one may be used in the preparation of 1-(2-chlorophenyl)-3-methylchromeno[2,3-c]pyrazol-4(1H)-one, a heterocyclic analog of xanthone.

InChI:InChI=1/C10H9ClN2O/c1-7-6-10(14)13(12-7)9-5-3-2-4-8(9)11/h2-5H,6H2,1H3

Upstream product

• 141-97-9 ethyl acetoacetate 
• 10449-07-7 (2-chlorophenyl)hydrazine 
• 41052-75-9 o-chlorophenylhydrazine hydrochloride 
• 89-25-8 edaravone 
• 95-51-2 o-chloroaniline 

Downstream Products

• 67365-78-0 2-(2-chloro-phenyl)-4-furfurylidene-5-methyl-2,4-dihydro-pyrazol-3-one 
• 85094-16-2 1-(2-Chloro-phenyl)-3,4-dimethyl-1H-pyrano[2,3-c]pyrazol-6-one 
• 67365-84-8 2-(2-chloro-phenyl)-4-furfuryl-5-methyl-1,2-dihydro-pyrazol-3-one 
• 67365-87-1 2-(2-chloro-phenyl)-5-methyl-4-(5-nitro-furan-2-ylmethyl)-1,2-dihydro-pyrazol-3-one 
• 1415230-71-5 1-(2-chlorophenyl)-3-methyl-4-(3-oxobutyl)-1H-pyrazol-5-yl acetate 
• 1415230-95-3 4,4'-(1-(2-chlorophenyl)-3-methyl-5-oxo-4,5-dihydro-1H-pyrazole-4,4-diyl)bis(butan-2-one) 
• 1415230-65-7 1-(2-chlorophenyl)-3-methyl-1H-pyrazol-5-yl acetate 

Relevant articles and documents

Discovery of novel inhibitors of human phosphoglycerate dehydrogenase by activity-directed combinatorial chemical synthesis strategy

Serine, the source of the one-carbon units essential for de novo purine and deoxythymidine synthesis plays a crucial role in the growth of cancer cells. Phosphoglycerate dehydrogenase (PHGDH) which catalyzes the first, rate-limiting step in de novo serine biosynthesis has become a promising target for the cancer treatment. Here we identified H-G6 as a potential PHGDH inhibitor from the screening of an in-house small molecule library based on the enzymatic assay. We adopted activity-directed combinatorial chemical synthesis strategy to optimize this hit compound. Compound b36 was found to be the noncompetitive and the most promising one with IC50 values of 5.96 ± 0.61 μM against PHGDH. Compound b36 inhibited the proliferation of human breast cancer and ovarian cancer cells, reduced intracellular serine synthesis, damaged DNA synthesis, and induced cell cycle arrest. Collectively, our results suggest that b36 is a novel PHGDH inhibitor, which could be a promising modulator to reprogram the serine synthesis pathway and might be a potential anticancer lead worth further exploration.

Synthesis of pyrazolones and pyrazoles via Pd-catalyzed aerobic oxidative dehydrogenation

A palladium-catalyzed oxidative dehydrogenation reaction in the presence of AMS and base to synthesize pyrazolones and pyrazoles was identified. This method can be utilized to a wide range of substrates, operates under mild react conditions and can give high yields. We believe it could be used as an alternative protocol for the classical dehydrogenation reactions.

DABCO-catalyzed silver-promoted direct thiolation of pyrazolones with diaryl disulfides

A highly efficient protocol for a direct thiolation of N-substituted pyrazolones with diaryl disulfides is described. Using a combination of DABCO and silver(i) acetate, the C-S bond formation proceeds smoothly at room temperature under mild and easy to handle conditions. This synthetic strategy offers a convenient and direct modification of antipyrine and other pyrazolone substrates, giving a series of aryl sulfide-substituted pyrazolone products in moderate to excellent yields.