1-Phenyl-4-methyl-3-pyrazolidone supplier

Name
1-Phenyl-4-methyl-3-pyrazolidone
EINECS 220-180-6
CAS No. 2654-57-1
Article Data8
CAS DataBase
Density 1.126 g/cm³
Solubility 754.801mg/L at 30℃
Melting Point 133-136 °C
Formula C₁₀H₁₂N₂O
Boiling Point 306.6 °C at 760 mmHg
Molecular Weight 176.218
Flash Point 139.2 °C
Transport Information UN 2811
Appearance Slightly yellow to beige fine crystalline powder
Safety 24/25
Risk Codes 22-43-51/53
Molecular Structure
Hazard Symbols Xn, N
Synonyms 1-Phenyl-4-methyl-3-oxopyrazolidine;1-Phenyl-4-methyl-3-pyrazolidinone;4-Methyl-1-phenyl-3-pyrazolidinone;4-Methyl-1-phenyl-3-pyrazolidone;4-Methyl-1-phenyl-4,5-dihydro-1H-pyrazol-3-ol;NSC 96628;Phenidone B;
PSA 32.34000
LogP 1.56770

Synthetic route

: 79-39-0
Methacrylamide

: 100-63-0
phenylhydrazine

: 2654-57-1
4-methyl-1-phenyl-1H-pyrazolidin-3-one

Conditions

Conditions	Yield
With sodium ethanolate

: 80-62-6
methacrylic acid methyl ester

: 100-63-0
phenylhydrazine

: 2654-57-1
4-methyl-1-phenyl-1H-pyrazolidin-3-one

Conditions

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

: 80-62-6
methacrylic acid methyl ester

: 100-63-0
phenylhydrazine

A: 2654-57-1
4-methyl-1-phenyl-1H-pyrazolidin-3-one

B: 14776-41-1
4-methyl-2-phenyl-pyrazolidin-3-one

C 4-methyl-1-phenyl-Δ2-pyrazolidin-5-one: 4-methyl-1-phenyl-Δ2-pyrazolidin-5-one

D 4-methyl-1-phenyl-Δ4-pyrazolidin-3-one: 4-methyl-1-phenyl-Δ4-pyrazolidin-3-one

...Expand

: C11H12N2O2

: 2654-57-1
4-methyl-1-phenyl-1H-pyrazolidin-3-one

Conditions

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

: 888501-00-6
2-allyl-4-methyl-1-phenyl-pyrazolidin-3-one

: 2654-57-1
4-methyl-1-phenyl-1H-pyrazolidin-3-one

Conditions

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

: 888501-01-7
C13H16N2O

: 2654-57-1
4-methyl-1-phenyl-1H-pyrazolidin-3-one

Conditions

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

: 2654-57-1
4-methyl-1-phenyl-1H-pyrazolidin-3-one

: 80335-74-6
N-cyclopentyl-O-benzoylhydroxylamine

: 1-[2-(cyclopentylamino)phenyl]-4-methyl-3-pyrazolidinone

Conditions

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

: 2654-57-1
4-methyl-1-phenyl-1H-pyrazolidin-3-one

: 501-65-5
diphenyl acetylene

: 3-(2,3-diphenyl-1H-indol-1-yl)-2-methylpropanamide

Conditions

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%

: 2654-57-1
4-methyl-1-phenyl-1H-pyrazolidin-3-one

: 15763-55-0
4-methyl-1-phenyl-1,2-dihydro-3H-pyrazol-3-one

Conditions

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

: 2654-57-1
4-methyl-1-phenyl-1H-pyrazolidin-3-one

: 308805-77-8
1-(2-phenylethynyl)-1-cyclobutanol

: 2-methyl-9-(2-oxopentyl)-9-phenyl-2,3-dihydro-1H,9H-pyrazolo[1,2-a]indazol-1-one

Conditions

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%

: 2654-57-1
4-methyl-1-phenyl-1H-pyrazolidin-3-one

: 106-95-6
allyl bromide

: 888501-00-6
2-allyl-4-methyl-1-phenyl-pyrazolidin-3-one

Conditions

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

: 2654-57-1
4-methyl-1-phenyl-1H-pyrazolidin-3-one

: 201230-82-2
carbon monoxide

: 40400-15-5
2-(2-iodophenyl)acetonitrile

: 1178576-80-1
3-methyl-9-oxo-1-phenyl-1,2,3,9-tetrahydro-pyrazolo[1,5-b]isoquinoline-4-carbonitrile

Conditions

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

...Expand

: 2654-57-1
4-methyl-1-phenyl-1H-pyrazolidin-3-one

: 61423-02-7
ethyl 1,1-dimethyl-3-phenylpropargyl acetate

: 2,5,5-trimethyl-7-phenyl-1,2-dihydro-3H,5H-benzo[c]pyrazolo[1,2-a][1,2]diazepin-3-one

Conditions

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

: 2654-57-1
4-methyl-1-phenyl-1H-pyrazolidin-3-one

: 201230-82-2
carbon monoxide

: ethyl 2-(3,4-methylenedioxy-6-iodophenyl)acetate

: 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

Conditions

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

...Expand

: 2654-57-1
4-methyl-1-phenyl-1H-pyrazolidin-3-one

: 308805-77-8
1-(2-phenylethynyl)-1-cyclobutanol

: 3-(2-butyryl-3-phenyl-1H-indol-1-yl)-2-methylpropanamide

Conditions

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

: 2654-57-1
4-methyl-1-phenyl-1H-pyrazolidin-3-one

: 201230-82-2
carbon monoxide

: 90794-29-9
ethyl 2-(2-iodophenyl)acetate

: 1178576-66-3
3-methyl-9-oxo-1-phenyl-1,2,3,9-tetrahydro-pyrazolo[1,5-b]isoquinoline-4-carboxylic acid ethyl ester

Conditions

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

...Expand

: 2654-57-1
4-methyl-1-phenyl-1H-pyrazolidin-3-one

: 201230-82-2
carbon monoxide

: 470662-16-9
ethyl 2-(2-iodo-4,5-dimethoxyphenyl)acetate

: 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

Conditions

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

...Expand

: 2654-57-1
4-methyl-1-phenyl-1H-pyrazolidin-3-one

: 201230-82-2
carbon monoxide

: 1178576-94-7
2-benzenesulfonylmethyl-4-bromo-1-iodo-benzene

: 1178577-01-9
4-benzenesulfonyl-6-bromo-3-methyl-1-phenyl-2,3-dihydro-1H-pyrazolo[1,5-b]isoquinolin-9-one

Conditions

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

...Expand

: 2654-57-1
4-methyl-1-phenyl-1H-pyrazolidin-3-one

: 201230-82-2
carbon monoxide

: 809233-22-5
2-(2-iodo-3,4-methylenedioxyphenyl)acetonitrile

: 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

Conditions

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

...Expand

: 2654-57-1
4-methyl-1-phenyl-1H-pyrazolidin-3-one

: 3-chloro-4-methyl-1-phenyl-4,5-dihydro-1H-pyrazole

Conditions

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

: 2654-57-1
4-methyl-1-phenyl-1H-pyrazolidin-3-one

: 201230-82-2
carbon monoxide

: 167708-86-3
1-iodo-2-(phenylsulfonylmethyl)benzene

: 1178576-98-1
4-benzenesulfonyl-3-methyl-1-phenyl-2,3-dihydro-1H-pyrazolo[1,5-b]isoquinolin-9-one

Conditions

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

...Expand

: 2654-57-1
4-methyl-1-phenyl-1H-pyrazolidin-3-one

: 98-88-4
benzoyl chloride

: 313472-70-7
benzoic acid 4-methyl-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl ester

Conditions

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

: 2654-57-1
4-methyl-1-phenyl-1H-pyrazolidin-3-one

: 201230-82-2
carbon monoxide

: 138450-22-3
1-bromo-2-(phenylsulfonylmethyl)naphthalene

: 1178577-19-9
7-benzenesulfonyl-8-methyl-10-phenyl-9,10-dihydro-8H-10,10a-diazacyclopenta[b]phenanthren-11-one

Conditions

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

...Expand

: 2654-57-1
4-methyl-1-phenyl-1H-pyrazolidin-3-one

: 860761-90-6
3-hydroxy-4-methyl-1-(4-nitro-phenyl)-1H-pyrazole

Conditions

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%

: 2654-57-1
4-methyl-1-phenyl-1H-pyrazolidin-3-one

: 6482-24-2
2-Bromoethyl methyl ether

: 133043-37-5
4-Methoxymethyl-4-methyl-1-phenyl-pyrazolidin-3-one

Conditions

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;

: 2654-57-1
4-methyl-1-phenyl-1H-pyrazolidin-3-one

A: 3-anilino-2-methyl-N-<4-(4-methyl-3-oxopyrazolin-1-yl)-phenyl>propionamide

B: 15763-55-0
4-methyl-1-phenyl-1,2-dihydro-3H-pyrazol-3-one

Conditions

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

: 106-31-0
butanoic acid anhydride

: 2654-57-1
4-methyl-1-phenyl-1H-pyrazolidin-3-one

: 2-butyryl-4-methyl-1-phenyl-pyrazolidin-3-one

Conditions

Conditions	Yield
at 130 - 150℃; Acylation;

: 2654-57-1
4-methyl-1-phenyl-1H-pyrazolidin-3-one

: 79-03-8
propionyl chloride

: propionic acid 4-methyl-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl ester

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran Acylation;

: 2654-57-1
4-methyl-1-phenyl-1H-pyrazolidin-3-one

: 123-62-6
propionic acid anhydride

: 4-methyl-1-phenyl-2-propionyl-pyrazolidin-3-one

Conditions

Conditions	Yield
at 130 - 150℃; Acylation;

: 2654-57-1
4-methyl-1-phenyl-1H-pyrazolidin-3-one

: 93-97-0
benzoic acid anhydride

: 313472-70-7
benzoic acid 4-methyl-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl ester

Conditions

Conditions	Yield
at 50℃; Acylation;

: 2654-57-1
4-methyl-1-phenyl-1H-pyrazolidin-3-one

: 141-75-3
butyryl chloride

: butyric acid 4-methyl-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl ester

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran Acylation;

1-Phenyl-4-methyl-3-pyrazolidone Chemical Properties

IUPAC Name: 4-methyl-1-phenylpyrazolidin-3-one
Empirical Formula: C₁₀H₁₂N₂O
Molecular Weight: 176.2151g/mol
EINECS: 220-180-6
Structure of 3-Pyrazolidinone,4-methyl-1-phenyl- (CAS NO.2654-57-1):

Index of Refraction: 1.552
Molar Refractivity: 50.03 cm³
Molar Volume: 156.4 cm³
Polarizability: 19.83×10^-24cm³
Surface Tension: 39.4 dyne/cm
Density: 1.126 g/cm³
Flash Point: 139.2 °C
Enthalpy of Vaporization: 57.77 kJ/mol
Boiling Point: 306.6 °C at 760 mmHg
Melting Point: 133-136 °C
storage temp: Dark Room
Vapour Pressure: 0.000333 mmHg at 25°C
Product Categories: Pyrazoles & Triazoles;Pyrazoles & Triazoles
Canonical SMILES: CC1CN(NC1=O)C2=CC=CC=C2
InChI: InChI=1S/C10H12N2O/c1-8-7-12(11-10(8)13)9-5-3-2-4-6-9/h2-6,8H,7H2,1H3,(H,11,13)
InChIKey: ZZEYCGJAYIHIAZ-UHFFFAOYSA-N

1-Phenyl-4-methyl-3-pyrazolidone Safety Profile

Hazard Codes: Harmful Xn, Dangerous N
Risk Statements: 22-43-51/53
R22:Harmful if swallowed.
R43:May cause sensitization by skin contact.
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements: 24/25
S24/25:Avoid contact with skin and eyes.
RIDADR: 2811
HazardClass: 6.1(b)
PackingGroup: III

1-Phenyl-4-methyl-3-pyrazolidone Specification

3-Pyrazolidinone,4-methyl-1-phenyl- , its cas register number is 2654-57-1. It also can be called 1-Phenyl-4-methyl-3-pyrazolidone ; 4-Methyl-1-phenyl-3-pyrazolidinone ; AI3-60150 ; NSC 96628 ; Phenidone B . 3-Pyrazolidinone,4-methyl-1-phenyl- (CAS NO.2654-57-1) toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. And it is harmful if swallowed.

Product Name

1-Phenyl-4-methyl-3-pyrazolidone

Synthetic route

1-Phenyl-4-methyl-3-pyrazolidone Chemical Properties

1-Phenyl-4-methyl-3-pyrazolidone Safety Profile

1-Phenyl-4-methyl-3-pyrazolidone Specification

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