2654-57-1

Basic information

• Product Name: 1-Phenyl-4-methyl-3-pyrazolidone
• Synonyms: PYRAZOLIDONE B;PHENIDONE B;1-Phenyl-4-methyl-3-pyrazolido;4-methyl-1-phenyl-3-pyrazolidinon;AKOS B028768;4-METHYL-1-PHENYLPYRAZOLIDIN-3-ONE;4-METHYL-1-PHENYL-3-PYRAZOLIDINONE;4-METHYL-1-PHENYL-3-PYRAZOLIDONE
• CAS NO: 2654-57-1
• Molecular Formula: C₁₀H₁₂N₂O
• Molecular Weight: 176.22
• EINECS: 220-180-6
• Product Categories: Pyrazoles & Triazoles;Pyrazoles & Triazoles
• Mol File: 2654-57-1.mol
• Article Data: 1

Chemical Properties

• Melting Point: 133-136 °C
• Boiling Point: 307.83°C (rough estimate)
• Flash Point: 139.2 °C
• Appearance: Slightly yellow to beige fine crystalline powder
• Density: 1.1102 (rough estimate)
• Vapor Pressure: 0.001Pa at 25℃
• Refractive Index: 1.7110 (estimate)
• Storage Temp.: Dark Room
• Solubility: soluble in Methanol
• PKA: 9.54±0.70(Predicted)
• Water Solubility: 754.801mg/L at 30℃
• CAS DataBase Reference: 1-Phenyl-4-methyl-3-pyrazolidone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Phenyl-4-methyl-3-pyrazolidone(2654-57-1)
• EPA Substance Registry System: 1-Phenyl-4-methyl-3-pyrazolidone(2654-57-1)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-43-51/53
• Safety Statements: 24/25
• RIDADR: 2811
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 2654-57-1(Hazardous Substances Data)

Usage

Flammability and Explosibility

Notclassified

InChI:InChI=1/C10H12N2O/c1-8-7-12(11-10(8)13)9-5-3-2-4-6-9/h2-6,8H,7H2,1H3,(H,11,13)/t8-/m1/s1

Synthetic route

Methacrylamide (79-39-0) + phenylhydrazine (100-63-0) → 4-methyl-1-phenyl-1H-pyrazolidin-3-one (2654-57-1)

Conditions	Yield
With sodium ethanolate

methacrylic acid methyl ester (80-62-6) + phenylhydrazine (100-63-0) → 4-methyl-1-phenyl-1H-pyrazolidin-3-one (2654-57-1)

Conditions	Yield
With acetic acid at 150℃;
With sodium ethanolate

methacrylic acid methyl ester (80-62-6) + phenylhydrazine (100-63-0) → 4-methyl-1-phenyl-1H-pyrazolidin-3-one (2654-57-1) + 4-methyl-2-phenyl-pyrazolidin-3-one (14776-41-1) + 4-methyl-1-phenyl-Δ2-pyrazolidin-5-one + 4-methyl-1-phenyl-Δ4-pyrazolidin-3-one

C11H12N2O2 → 4-methyl-1-phenyl-1H-pyrazolidin-3-one (2654-57-1)

Conditions	Yield
With sodium hydrogencarbonate; sodium carbonate In acetone	35 mg

2-allyl-4-methyl-1-phenyl-pyrazolidin-3-one (888501-00-6) → 4-methyl-1-phenyl-1H-pyrazolidin-3-one (2654-57-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 87 percent / [(PCy3)2Cl2Ru=CHPh] / toluene / 110 °C 2: NaIO4; aq. RuCl3 / 1,2-dichloro-ethane / 20 °C 3: 35 mg / aq. NaHCO3; Na2CO3 / acetone View Scheme

C13H16N2O (888501-01-7) → 4-methyl-1-phenyl-1H-pyrazolidin-3-one (2654-57-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaIO4; aq. RuCl3 / 1,2-dichloro-ethane / 20 °C 2: 35 mg / aq. NaHCO3; Na2CO3 / acetone View Scheme

4-methyl-1-phenyl-1H-pyrazolidin-3-one (2654-57-1) + N-cyclopentyl-O-benzoylhydroxylamine (80335-74-6) → 1-[2-(cyclopentylamino)phenyl]-4-methyl-3-pyrazolidinone

Conditions	Yield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; cesium acetate; Trimethylacetic acid In toluene at 20℃;	96%

4-methyl-1-phenyl-1H-pyrazolidin-3-one (2654-57-1) + diphenyl acetylene (501-65-5) → 3-(2,3-diphenyl-1H-indol-1-yl)-2-methylpropanamide

Conditions	Yield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; palladium diacetate; sodium carbonate In 1,2-dichloro-ethane at 100℃; for 2h; Sealed tube;	95%
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; sodium acetate In chlorobenzene at 110℃; for 18h; Schlenk technique; Inert atmosphere; regioselective reaction;	93%

4-methyl-1-phenyl-1H-pyrazolidin-3-one (2654-57-1) → 4-methyl-1-phenyl-1,2-dihydro-3H-pyrazol-3-one (15763-55-0)

Conditions	Yield
With sodium anthraquinone-2-sulfonate; palladium diacetate; potassium carbonate In chlorobenzene at 110℃; for 6h;	93%
With trifluoro-N-(oxo-λ4-sulfanylidene)methanesulfonamide In dichloromethane at 20℃; Inert atmosphere;	88%
With iron(III) chloride

4-methyl-1-phenyl-1H-pyrazolidin-3-one (2654-57-1) + 1-(2-phenylethynyl)-1-cyclobutanol (308805-77-8) → 2-methyl-9-(2-oxopentyl)-9-phenyl-2,3-dihydro-1H,9H-pyrazolo[1,2-a]indazol-1-one

Conditions	Yield
With copper(l) iodide; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; sodium carbonate In 1,2-dichloro-ethane at 50℃; for 12h; Inert atmosphere;	91%
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; sodium acetate In dichloromethane at 60℃; for 8h;	45%

4-methyl-1-phenyl-1H-pyrazolidin-3-one (2654-57-1) + allyl bromide (106-95-6) → 2-allyl-4-methyl-1-phenyl-pyrazolidin-3-one (888501-00-6)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃;	89%

4-methyl-1-phenyl-1H-pyrazolidin-3-one (2654-57-1) + carbon monoxide (201230-82-2) + 2-(2-iodophenyl)acetonitrile (40400-15-5) → 3-methyl-9-oxo-1-phenyl-1,2,3,9-tetrahydro-pyrazolo[1,5-b]isoquinoline-4-carbonitrile (1178576-80-1)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate; triphenylphosphine In tetrahydrofuran at 80℃; under 5171.62 Torr; for 4h;	84%

4-methyl-1-phenyl-1H-pyrazolidin-3-one (2654-57-1) + ethyl 1,1-dimethyl-3-phenylpropargyl acetate (61423-02-7) → 2,5,5-trimethyl-7-phenyl-1,2-dihydro-3H,5H-benzo[c]pyrazolo[1,2-a][1,2]diazepin-3-one

Conditions	Yield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; sodium acetate In 1,2-dichloro-ethane at 100℃; for 12h;	82%

4-methyl-1-phenyl-1H-pyrazolidin-3-one (2654-57-1) + carbon monoxide (201230-82-2) + ethyl 2-(3,4-methylenedioxy-6-iodophenyl)acetate → 8-methyl-5-oxo-6-phenyl-5,6,7,8-tetrahydro-1,3-dioxa-5a,6-diazadicyclopenta[b,g]naphthalene-9-carboxylic acid ethyl ester (1178576-73-2)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate; triphenylphosphine In tetrahydrofuran at 80℃; under 5171.62 Torr; for 4h;	72%

4-methyl-1-phenyl-1H-pyrazolidin-3-one (2654-57-1) + 1-(2-phenylethynyl)-1-cyclobutanol (308805-77-8) → 3-(2-butyryl-3-phenyl-1H-indol-1-yl)-2-methylpropanamide

Conditions	Yield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; sodium carbonate In tetrahydrofuran at 100℃; for 2h;	71%

4-methyl-1-phenyl-1H-pyrazolidin-3-one (2654-57-1) + carbon monoxide (201230-82-2) + ethyl 2-(2-iodophenyl)acetate (90794-29-9) → 3-methyl-9-oxo-1-phenyl-1,2,3,9-tetrahydro-pyrazolo[1,5-b]isoquinoline-4-carboxylic acid ethyl ester (1178576-66-3)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate; triphenylphosphine In tetrahydrofuran at 80℃; under 5171.62 Torr; for 4h;	70%

4-methyl-1-phenyl-1H-pyrazolidin-3-one (2654-57-1) + carbon monoxide (201230-82-2) + ethyl 2-(2-iodo-4,5-dimethoxyphenyl)acetate (470662-16-9) → 6,7-dimethoxy-3-methyl-9-oxo-1-phenyl-1,2,3,9-tetrahydropyrazolo[1,5-b]isoquinoline-4-carboxylic acid ethyl ester (1178576-70-9)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate; triphenylphosphine In tetrahydrofuran at 80℃; under 5171.62 Torr; for 4h;	65%

4-methyl-1-phenyl-1H-pyrazolidin-3-one (2654-57-1) + carbon monoxide (201230-82-2) + 2-benzenesulfonylmethyl-4-bromo-1-iodo-benzene (1178576-94-7) → 4-benzenesulfonyl-6-bromo-3-methyl-1-phenyl-2,3-dihydro-1H-pyrazolo[1,5-b]isoquinolin-9-one (1178577-01-9)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate; triphenylphosphine In tetrahydrofuran at 80℃; under 5171.62 Torr; for 4h;	61%

4-methyl-1-phenyl-1H-pyrazolidin-3-one (2654-57-1) + carbon monoxide (201230-82-2) + 2-(2-iodo-3,4-methylenedioxyphenyl)acetonitrile (809233-22-5) → 8-methyl-5-oxo-6-phenyl-5,6,7,8-tetrahydro-1,3-dioxa-5a,6-diazadicyclopenta[b,g]naphthalene-9-carbonitrile (1178576-86-7)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate; triphenylphosphine In tetrahydrofuran at 80℃; under 5171.62 Torr; for 4h;	61%

4-methyl-1-phenyl-1H-pyrazolidin-3-one (2654-57-1) → 3-chloro-4-methyl-1-phenyl-4,5-dihydro-1H-pyrazole

Conditions	Yield
With trichlorophosphate In toluene at 70℃;	58%

4-methyl-1-phenyl-1H-pyrazolidin-3-one (2654-57-1) + carbon monoxide (201230-82-2) + 1-iodo-2-(phenylsulfonylmethyl)benzene (167708-86-3) → 4-benzenesulfonyl-3-methyl-1-phenyl-2,3-dihydro-1H-pyrazolo[1,5-b]isoquinolin-9-one (1178576-98-1)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate; triphenylphosphine In tetrahydrofuran at 80℃; under 5171.62 Torr; for 4h;	58%

4-methyl-1-phenyl-1H-pyrazolidin-3-one (2654-57-1) + benzoyl chloride (98-88-4) → benzoic acid 4-methyl-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl ester (313472-70-7)

Conditions	Yield
With triethylamine In tetrahydrofuran for 12h; Acylation;	53%

4-methyl-1-phenyl-1H-pyrazolidin-3-one (2654-57-1) + carbon monoxide (201230-82-2) + 1-bromo-2-(phenylsulfonylmethyl)naphthalene (138450-22-3) → 7-benzenesulfonyl-8-methyl-10-phenyl-9,10-dihydro-8H-10,10a-diazacyclopenta[b]phenanthren-11-one (1178577-19-9)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 110℃; under 10343.2 Torr; for 24h;	50%

4-methyl-1-phenyl-1H-pyrazolidin-3-one (2654-57-1) → 3-hydroxy-4-methyl-1-(4-nitro-phenyl)-1H-pyrazole (860761-90-6)

Conditions	Yield
Stage #1: 4-methyl-1-phenyl-1H-pyrazolidin-3-one With sulfuric acid at -5℃; for 0.0833333h; Stage #2: With nitric acid In water at -20 - -5℃; for 1h;	40%

4-methyl-1-phenyl-1H-pyrazolidin-3-one (2654-57-1) + 2-Bromoethyl methyl ether (6482-24-2) → 4-Methoxymethyl-4-methyl-1-phenyl-pyrazolidin-3-one (133043-37-5)

Conditions	Yield
With n-butyllithium; N,N,N,N,-tetramethylethylenediamine 1.) THF, hexane, from -78 deg C to 0 deg C, 2.5 h, 2.) THF, -78 deg C, 2 h; Yield given. Multistep reaction;

4-methyl-1-phenyl-1H-pyrazolidin-3-one (2654-57-1) → 3-anilino-2-methyl-N-<4-(4-methyl-3-oxopyrazolin-1-yl)-phenyl>propionamide + 4-methyl-1-phenyl-1,2-dihydro-3H-pyrazol-3-one (15763-55-0)

Conditions	Yield
In acetonitrile 0.6V, 0.1M-Et4NBF4 electrolyte, other electrolyte, other potential;	A 0.1 g B 0.1 g

butanoic acid anhydride (106-31-0) + 4-methyl-1-phenyl-1H-pyrazolidin-3-one (2654-57-1) → 2-butyryl-4-methyl-1-phenyl-pyrazolidin-3-one

Conditions	Yield
at 130 - 150℃; Acylation;

4-methyl-1-phenyl-1H-pyrazolidin-3-one (2654-57-1) + propionyl chloride (79-03-8) → propionic acid 4-methyl-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl ester

Conditions	Yield
With triethylamine In tetrahydrofuran Acylation;

4-methyl-1-phenyl-1H-pyrazolidin-3-one (2654-57-1) + propionic acid anhydride (123-62-6) → 4-methyl-1-phenyl-2-propionyl-pyrazolidin-3-one

Conditions	Yield
at 130 - 150℃; Acylation;

4-methyl-1-phenyl-1H-pyrazolidin-3-one (2654-57-1) + benzoic acid anhydride (93-97-0) → benzoic acid 4-methyl-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl ester (313472-70-7)

Conditions	Yield
at 50℃; Acylation;

4-methyl-1-phenyl-1H-pyrazolidin-3-one (2654-57-1) + butyryl chloride (141-75-3) → butyric acid 4-methyl-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl ester

Conditions	Yield
With triethylamine In tetrahydrofuran Acylation;

Upstream product

• 888501-01-7 C₁₃H₁₆N₂O 
• 888501-00-6 2-allyl-4-methyl-1-phenyl-pyrazolidin-3-one 
• 80-62-6 methacrylic acid methyl ester 
• 100-63-0 phenylhydrazine 
• 79-39-0 Methacrylamide 

Downstream Products

• 888501-00-6 2-allyl-4-methyl-1-phenyl-pyrazolidin-3-one 
• 1178576-86-7 8-methyl-5-oxo-6-phenyl-5,6,7,8-tetrahydro-1,3-dioxa-5a,6-diazadicyclopenta[b,g]naphthalene-9-carbonitrile 
• 1178576-70-9 6,7-dimethoxy-3-methyl-9-oxo-1-phenyl-1,2,3,9-tetrahydropyrazolo[1,5-b]isoquinoline-4-carboxylic acid ethyl ester 
• 1178576-73-2 8-methyl-5-oxo-6-phenyl-5,6,7,8-tetrahydro-1,3-dioxa-5a,6-diazadicyclopenta[b,g]naphthalene-9-carboxylic acid ethyl ester 
• 1178576-98-1 4-benzenesulfonyl-3-methyl-1-phenyl-2,3-dihydro-1H-pyrazolo[1,5-b]isoquinolin-9-one 
• 1178577-19-9 7-benzenesulfonyl-8-methyl-10-phenyl-9,10-dihydro-8H-10,10a-diazacyclopenta[b]phenanthren-11-one 
• 1178576-66-3 3-methyl-9-oxo-1-phenyl-1,2,3,9-tetrahydro-pyrazolo[1,5-b]isoquinoline-4-carboxylic acid ethyl ester 
• 1178576-80-1 3-methyl-9-oxo-1-phenyl-1,2,3,9-tetrahydro-pyrazolo[1,5-b]isoquinoline-4-carbonitrile 
• 1178577-01-9 4-benzenesulfonyl-6-bromo-3-methyl-1-phenyl-2,3-dihydro-1H-pyrazolo[1,5-b]isoquinolin-9-one 
• 95883-60-6 (+/-)-4,5-Dihydro-N-(4-methoxyphenyl)-4-methyl-1-phenyl-1H-pyrazol-3-amine 
• 860761-90-6 3-hydroxy-4-methyl-1-(4-nitro-phenyl)-1H-pyrazole 
• 313472-70-7 benzoic acid 4-methyl-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl ester 

Relevant articles and documents

A practical ruthenium-catalyzed cleavage of the allyl protecting group in amides, lactams, imides, and congeners

A convenient methodology for the deprotection of N-allylic amide-like moieties was developed. The first examples accounting for the ruthenium-catalyzed deallylation of amides, lactams, imides, pyrazolidones, hydantoins, and oxazolidinones have been achieved by the sequential use of Grubbs carbene (isomerization step) and RuCl3 (oxidation step). A variety of substrates, including enantiopure multifunctional β- and γ-lactams, can be employed.