68761-49-9

Basic information

• Product Name: 4-benzylidene-5-methyl-2,4-dihydro-3H-pyrazol-3-one
• CAS NO: 68761-49-9
• Molecular Formula: C₁₁H₁₀N₂O
• Molecular Weight: 186.2099
• Mol File: 68761-49-9.mol
• Article Data: 5

Chemical Properties

• Density: 1.17g/cm³
• Refractive Index: 1.609
• CAS DataBase Reference: 4-benzylidene-5-methyl-2,4-dihydro-3H-pyrazol-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-benzylidene-5-methyl-2,4-dihydro-3H-pyrazol-3-one(68761-49-9)
• EPA Substance Registry System: 4-benzylidene-5-methyl-2,4-dihydro-3H-pyrazol-3-one(68761-49-9)

Safety Data

• Hazardous Substances Data: 68761-49-9(Hazardous Substances Data)

Upstream product

• 90959-21-0 3-{3-Methyl-5-oxo-4-[1-phenyl-meth-(E)-ylidene]-4,5-dihydro-pyrazol-1-yl}-1-p-tolyl-pyrrolidine-2,5-dione 
• 90959-22-1 (E)-2-{3-Methyl-5-oxo-4-[1-phenyl-meth-(E)-ylidene]-4,5-dihydro-pyrazol-1-yl}-but-2-enedioic acid dimethyl ester 
• 90959-19-6 3-{3-Methyl-5-oxo-4-[1-phenyl-meth-(E)-ylidene]-4,5-dihydro-pyrazol-1-yl}-propionic acid ethyl ester 
• 90959-27-6 3-{3-Methyl-5-oxo-4-[1-phenyl-meth-(E)-ylidene]-4,5-dihydro-pyrazol-1-yl}-propionamide 
• 141-97-9 ethyl acetoacetate 
• 100-52-7 benzaldehyde 
• 108-26-9 3-methyl-2-pyrazoline-5-one 
• 90959-20-9 3-{3-Methyl-5-oxo-4-[1-phenyl-meth-(E)-ylidene]-4,5-dihydro-pyrazol-1-yl}-1-phenyl-pyrrolidine-2,5-dione 

Downstream Products

• 947339-36-8 C₂₁H₁₇N₃O₄ 
• 112701-03-8 4-benzyl-5-methyl-1,2-dihydro-3H-pyrazol-3-one 
• 90959-22-1 (E)-2-{3-Methyl-5-oxo-4-[1-phenyl-meth-(E)-ylidene]-4,5-dihydro-pyrazol-1-yl}-but-2-enedioic acid dimethyl ester 
• 90959-27-6 3-{3-Methyl-5-oxo-4-[1-phenyl-meth-(E)-ylidene]-4,5-dihydro-pyrazol-1-yl}-propionamide 
• 81000-11-5 6-amino-1,4-dihydro-3-methyl-4-phenylpyrano[2,3-c]pyrazole-5-carbonitrile 
• 96128-63-1 5-Methyl-4-[(3-methyl-1-phenyl-5-thioxo-4,5-dihydro-1H-pyrazol-4-yl)-phenyl-methyl]-2,4-dihydro-pyrazol-3-one 
• 96239-91-7 6-Amino-3-methyl-4-phenyl-1,4-dihydro-pyrano[2,3-c]pyrazole-5-carboxylic acid hydrazide 
• 68761-33-1 3-Hydrazono-2-[1-phenyl-meth-(Z)-ylidene]-butyric acid hydrazide 
• 90959-19-6 3-{3-Methyl-5-oxo-4-[1-phenyl-meth-(E)-ylidene]-4,5-dihydro-pyrazol-1-yl}-propionic acid ethyl ester 

Relevant articles and documents

“On-water” one-pot four-component synthesis of novel 1H-furo[2,3-c]pyrazole-4-amine derivatives

A catalyst-free, simple and green protocol has been accomplished for the synthesis of novel 1H-furo[2,3-c]pyrazole-4-amines in a one-pot four-component domino reaction involving hydrazines, ethyl acetoacetate, aromatic amines and phenylglyoxal monohydrate in water. The protocol presented herein describes in situ generated pyrazolone as intermediate reactants with phenylglyoxal monohydrate in a Knoevenagel condensation followed by a Michael addition of amine, intramolecular cyclization, dehydration and the resulting to the title compound. It was observed that in this protocol bis(pyrazole-5-ols) are formed with amines bearing strong electron withdrawing groups under similar reaction conditions instead of the expected products. The reaction merits the use of water as solvent, no additive catalyst, easy workup, easy purification of products by non-chromatography and provides high yield of products with good purity.

Synthesis and bioactivity evaluation of pyrazolone derivatives

3-Methyl-4-substituted benzylidene-pyrazol-5-ones 1-10 are synthesized by the condensation of 3-methyl-pyrazol-5-one with substituted aliphatic and aromatic aldehydes. Their structures have been elucidated from UV-Vis, IR, 1H NMR and mass spectral data. Among the synthesized derivatives 5, 6, 7 and 10 are found to have a potent anti-inflammatory response whereas compounds 1, 4, 5, 8 and 10 have an effective analgesic response. There is no remarkable difference in bioactivity of pyrazolones derived from aliphatic and aromatic aldehydes. All the experimental data are statistically significant at p0.05.

Michael Addition of Ylidenpyrazolones

The reactivity of ylidenpyrazolones (1a-c) towards compounds bearing an activated double bond has been investigated.Ia on treatment with acrylonitrile furnishes the amide (II) while with ethyl acrylate, N-arylmaleimides and dimethyl acetylendicarboxylate, the Michael adducts (IV-VI) are obtained.The reaction of Ib and Ic with acrylonitrile and ethyl acetate gives the adducts VII.