1-(p-Tolyl)-3-methyl-5-pyrazolone supplier

Name
2,4-Dihydro-5-methyl-2-(4-methylphenyl)-3H-pyrazol-3-one
EINECS 201-708-4
CAS No. 86-92-0
Article Data29
CAS DataBase
Density 1.15 g/cm³
Solubility
Melting Point 129 °C
Formula C₁₁H₁₂N₂O
Boiling Point 365.1 °C at 760 mmHg
Molecular Weight 188.229
Flash Point 174.6 °C
Transport Information
Appearance Light yellow crystalline powder
Safety
Risk Codes 22
Molecular Structure
Hazard Symbols Xn
Synonyms 2-Pyrazolin-5-one,3-methyl-1-p-tolyl- (6CI,7CI,8CI);1-(p-Tolyl)-3-methylpyrazolone-5;1-p-Tolyl-3-methyl-5-pyrazolone;2,4-Dihydro-5-methyl-2-(4-methylphenyl)-3H-pyrazol-3-one;3-Methyl-1-(4-methylphenyl)-2-pyrazolin-5-one;3-Methyl-1-(4-methylphenyl)-5-pyrazolone;3-Methyl-1-(p-tolyl)-2-pyrazolin-5-one;3-Methyl-1-p-tolyl-5-pyrazolone;2,4-Dihydro-5-methyl-2-(4-methylphenyl)-3H-pyrazol-3-one;3H-pyrazol-3-one, 2,4-dihydro-5-methyl-2-(4-methylphenyl)-;5-methyl-2-(4-methylphenyl)-2,4-dihydro-3H-pyrazol-3-one;
PSA 32.67000
LogP 1.60820

Synthetic route

: 17028-79-4
5-methyl-2-p-tolylpyrazolidin-3-one

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

Conditions

Conditions	Yield
With sodium anthraquinone-2-sulfonate; palladium diacetate; potassium carbonate In chlorobenzene at 110℃; for 6h;	97%

: 674-82-8
4-methyleneoxetan-2-one

: 539-44-6
N-4-methylphenylhydrazine

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

Conditions

Conditions	Yield
Stage #1: 4-methyleneoxetan-2-one With ammonium hydroxide at 0℃; for 2h; Stage #2: N-4-methylphenylhydrazine at 15℃; for 2.5h; Stage #3: With hydrogenchloride In water for 0.5h; pH=1;	96.5%

: 141-97-9
ethyl acetoacetate

: 539-44-6
N-4-methylphenylhydrazine

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

Conditions

Conditions	Yield
With acetic acid at 100℃; for 1h;	83%
In ethanol Reflux;	65%
In ethanol for 3h; Heating;

: 624-31-7
4-tolyl iodide

: 108-26-9
3-methyl-2-pyrazoline-5-one

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

Conditions

Conditions	Yield
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine In acetonitrile Reflux; Inert atmosphere;	76%

: 637-60-5
p-tolylhydrazine hydrochloride

: 141-97-9
ethyl acetoacetate

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

Conditions

Conditions	Yield
With triethylamine In ethanol at 60℃; for 24h; Reflux;
With sodium acetate In acetic acid Reflux; Inert atmosphere;
Stage #1: p-tolylhydrazine hydrochloride With sodium acetate In ethanol; water at 20℃; for 0.0833333h; Stage #2: ethyl acetoacetate In ethanol; water for 3h; Reflux;

: 106-49-0
p-toluidine

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

: 105-45-3
acetoacetic acid methyl ester

: 539-44-6
N-4-methylphenylhydrazine

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

Conditions

Conditions	Yield
With acetic acid for 24h; Reflux;

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

: C11H12N2S

Conditions

Conditions	Yield
With Lawessons reagent In toluene Reflux;	100%
With Lawessons reagent In toluene for 2h; Reflux;	97%

: 102-96-5
(2-nitroethenyl)benzene

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

: 1451195-31-5
(R)-5-methyl-4-(2-nitro-1-phenylethyl)-2-p-tolyl-2H-pyrazol-3-ol

Conditions

Conditions	Yield
With quinine In chloroform at 20℃; for 14h; Michael Addition; enantioselective reaction;	99%

: 108-24-7
acetic anhydride

: 92210-53-2
3-nitro-2H-1-benzopyran

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

: 3-methyl-4-((3S,4S)-3-nitrochroman-4-yl)-1-(p-tolyl)-1H-pyrazol-5-yl acetate

Conditions

Conditions	Yield
Stage #1: 3-nitro-2H-1-benzopyran; 3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one With quinine In dichloromethane at -15℃; for 96h; Michael Addition; Stage #2: acetic anhydride With triethylamine In dichloromethane at 20℃; for 0.5h; enantioselective reaction;	98%

...Expand

: 100-63-0
phenylhydrazine

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

: 3-methyl-4-(phenyldiazenyl)-1-(p-tolyl)-1H-pyrazol-5-ol

Conditions

Conditions	Yield
With iodine; silver nitrate; acetic acid In 1,2-dichloro-ethane at 70℃; for 6h; Inert atmosphere;	97%

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

: 882-33-7
diphenyldisulfane

: 3-methyl-4-(phenylthio)-1-(p-tolyl)-1H-pyrazol-5-ol

Conditions

Conditions	Yield
With dihydrogen peroxide; iodine In 1,4-dioxane; decane; water at 25℃; for 24h;	97%

: 1147550-11-5
ammonium thiocyanate

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

: ammonium 3-methyl-4-thiocyanato-1-(p-tolyl)-1H-pyrazol-5-olate

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 3h; Electrochemical reaction;	97%

: tert-butyl (3-methyl-5-oxo-1-phenyl-1,5-dihydro-4H-pyrazol-4-ylidene)carbamate

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

: tert-butyl (S)-[5-hydroxy-3,3′-dimethyl-5′-oxo-1′-phenyl-1-(ptolyl)-1′,5′-dihydro-1H,4′H-[4,4′-bipyrazol]-4′-yl]carbamate

Conditions

Conditions	Yield
Stage #1: tert-butyl (3-methyl-5-oxo-1-phenyl-1,5-dihydro-4H-pyrazol-4-ylidene)carbamate With C32H28F6N4O3 In dichloromethane at -48℃; for 0.166667h; Molecular sieve; Stage #2: 3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one In dichloromethane at -48℃; for 24h; Molecular sieve; enantioselective reaction;	96%

: 2438-71-3
5-bromoisatin β-hydrazone

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

: 3-methyl-1-(p-tolyl)pyrazole-4,5-dione 4-(4-bromo-2-cyanophenyl)hydrazone

Conditions

Conditions	Yield
Stage #1: 5-bromoisatin β-hydrazone With sulfuric acid; acetic acid; sodium nitrite Stage #2: 3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one In ethanol at 20℃; for 1h;	94%

: 100-52-7
benzaldehyde

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

: 122-52-1
triethyl phosphite

: diethyl [(5-hydroxy-3-methyl-1-(p-tolyl)-1H-pyrazol-4-yl)(phenyl)-methyl]phosphonate

Conditions

Conditions	Yield
With palladium In ethanol at 20℃;	94%

...Expand

: 106-54-7
p-Chlorothiophenol

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

: 3-methyl-1-(4-methylphenyl)-4-(4-chlorophenylthio)-1H-pyrazole-5-ol

Conditions

Conditions	Yield
With dimethyl sulfoxide at 60 - 110℃; Sealed tube;	94%
With Pd(II)(NHC)Cl2; potassium carbonate In N,N-dimethyl-formamide at 100℃; for 3h; regioselective reaction;	79%

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

: 4-bromo-2-cyano-benzenediazonium; hydrogen sulfate

: 3-methyl-1-(p-tolyl)pyrazole-4,5-dione 4-(4-bromo-2-cyanophenyl)hydrazone

Conditions

Conditions	Yield
In ethanol at 20℃; Condensation;	93.5%

: 358-23-6
trifluoromethylsulfonic anhydride

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

: 1373936-54-9
3-methyl-1-p-tolyl-1H-pyrazol-5-yl trifluoromethanesulfonate

Conditions

Conditions	Yield
With 2,4,6-tri-tertbutylpyridine In 1,2-dichloro-ethane at 0 - 20℃; Inert atmosphere;	93%

: 106-45-6
para-thiocresol

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

: 3-methyl-1-(4-methylphenyl)-4-(4-methyl-phenylthio)-1H-pyrazole-5-ol

Conditions

Conditions	Yield
With sodium hydroxide In acetonitrile at 60℃;	93%
With 5-ethyl-1,3,7,8-tetramethylalloxazinium triflate; iodine In acetonitrile at 25℃; under 760.051 Torr; for 24h; Green chemistry; chemoselective reaction;	91%
With Pd(II)(NHC)Cl2; potassium carbonate In N,N-dimethyl-formamide at 100℃; for 3h; regioselective reaction;	84%
With dimethyl sulfoxide at 60 - 110℃; Sealed tube;	64%

: 86-93-1
1-Phenyl-1H-tetrazole-5-thiol

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

: 3-methyl-4-((1-phenyl-1H-tetrazol-5-yl)thio)-1-(p-tolyl)-1H-pyrazol-5-ol

Conditions

Conditions	Yield
With iodine In dimethyl sulfoxide at 80℃; for 1.5h; Green chemistry;	93%

: 935749-19-2
acetic acid 1-phenyl-buta-2,3-dienyl ester

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

: (E)-3-methyl-4-phenyl-6-(4-phenylbuta-1,3-dien-2-yl)-1-(p-tolyl)-4,7-dihydro-1H-oxepino[2,3-c]pyrazole

Conditions

Conditions	Yield
With dichloro(1,5-cyclooctadiene)palladium(II); potassium carbonate; triphenylphosphine In chloroform at 30℃; for 10h; Inert atmosphere; stereoselective reaction;	93%

: 1191-99-7
2,3-dihydro-2H-furan

: 110912-15-7
3-chloro-1H-indole-2-carboxaldehyde

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

: C24H22ClN3O2

Conditions

Conditions	Yield
With triethylammonium acetate for 0.183333h; Microwave irradiation; Green chemistry;	92%

...Expand

: 73568-26-0
2-chloro-8-methyl-quinoline-3-carbaldehyde

: 109-92-2
ethyl vinyl ether

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

: C26H26ClN3O2

Conditions

Conditions	Yield
With triethylammonium acetate for 0.183333h; Microwave irradiation; Green chemistry;	91%

...Expand

: 73568-26-0
2-chloro-8-methyl-quinoline-3-carbaldehyde

: 928-55-2
ethyl 1-propenyl ether

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

: C27H28ClN3O2

Conditions

Conditions	Yield
With triethylammonium acetate for 0.166667h; Microwave irradiation; Green chemistry;	91%

...Expand

: 591-50-4
iodobenzene

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

: 1543006-70-7
3-methyl-1-(5-methyl-[1,1'-biphenyl]-2-yl)-1H-pyrazol-5(4H)-one

Conditions

Conditions	Yield
With silver(I) acetate; palladium diacetate; trifluoroacetic acid at 120℃; for 5h;	91%

: 1747-60-0
6-methoxybenzothiazol-2-ylamine

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

: (6-methoxy-benzothiazol-2-yl)-(5-methyl-2-p-tolyl-2,4-dihydro-pyrazol-3-ylidene)-amine

Conditions

Conditions	Yield
In methanol for 0.025h; microwave irradiation;	90%

: 6285-57-0
2-amino-6-nitrobenzothiazole

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

: 1-(4'-methylphenyl)-3-methyl-5-(2''-imino-6''-nitrobenzothiazole)pyrazole

Conditions

Conditions	Yield
In methanol for 0.0333333h; microwave irradiation;	90%

: 1191-99-7
2,3-dihydro-2H-furan

: 73568-26-0
2-chloro-8-methyl-quinoline-3-carbaldehyde

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

: C26H24ClN3O2

Conditions

Conditions	Yield
With triethylammonium acetate for 0.133333h; Microwave irradiation; Green chemistry;	90%

...Expand

: 928-55-2
ethyl 1-propenyl ether

: 110912-15-7
3-chloro-1H-indole-2-carboxaldehyde

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

: C25H28ClN3O2

Conditions

Conditions	Yield
With triethylammonium acetate for 0.15h; Microwave irradiation; Green chemistry;	90%

...Expand

: 2-methyl-2-(4-methylpent-3-en-1-yl)-2H-thiopyrano[2,3-b]quinoline-3-carbaldehyde

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

: (5aR,15bS)-1,5,5,7a-tetramethyl-3-(p-tolyl)-5,5a,6,7,7a,15bhexahydro-3H-pyrazolo[4'',3'':5',6']pyrano[4',3':5,6]thiochromeno[2,3-b]quinoline

Conditions

Conditions	Yield
With glycerol at 120℃; for 3h; Green chemistry;	90%

: 20718-17-6
2-(dimethyl(oxo)-λ6-sulfaneylidene)-1-phenylethan-1-one

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

: 3,8-dimethyl-5-phenyl-1H-pyrazolo[1,2-a]cinnolin-1-one

Conditions

Conditions	Yield
With silver hexafluoroantimonate; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; zinc trifluoromethanesulfonate; toluene-4-sulfonic acid at 120℃; for 12h; Sealed tube;	90%

: 79-03-8
propionyl chloride

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

: 151512-60-6
3-methyl-1-(4'-methylphenyl)-4-propionyl-2-pyrazolin-5-one

Conditions

Conditions	Yield
With calcium hydroxide In 1,4-dioxane for 2h; Reflux;	89%

: C21H23NOS

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

: (5aR,15bS)-1,5,5,7a,10-pentamethyl-3-(p-tolyl)-5,5a,6,7,7a,15b-hexahydro-3H-pyrazolo[4'',3'':5',6']pyrano[4',3':5,6]thiochromeno[2,3-b]quinoline

Conditions

Conditions	Yield
With glycerol at 120℃; for 3h; Green chemistry;	89%

: 100-32-3
di(p-nitrophenyl) disulfide

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

: C17H15N3O3S

Conditions

Conditions	Yield
With dihydrogen peroxide; iodine In 1,4-dioxane; decane; water at 25℃; for 24h;	89%

1-(p-Tolyl)-3-methyl-5-pyrazolone Consensus Reports

Reported in EPA TSCA Inventory.

1-(p-Tolyl)-3-methyl-5-pyrazolone Specification

The 1-(p-Tolyl)-3-methyl-5-pyrazolone, with the CAS registry number 86-92-0 and EINECS registry number 201-708-4, has the systematic name of 5-methyl-2-(4-methylphenyl)-2,4-dihydro-3H-pyrazol-3-one. It belongs to the product category of Intermediates of Dyes and Pigments. And the molecular formula of this chemical is C₁₁H₁₂N₂O.

The physical properties of 1-(p-Tolyl)-3-methyl-5-pyrazolone are as following: (1)ACD/LogP: 0.90; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.9; (4)ACD/LogD (pH 7.4): 0.9; (5)ACD/BCF (pH 5.5): 2.82; (6)ACD/BCF (pH 7.4): 2.82; (7)ACD/KOC (pH 5.5): 73.12; (8)ACD/KOC (pH 7.4): 73.18; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 32.67 Å²; (13)Index of Refraction: 1.595; (14)Molar Refractivity: 55.63 cm³; (15)Molar Volume: 163.6 cm³; (16)Polarizability: 22.05×10^-24cm³; (17)Surface Tension: 40.9 dyne/cm; (18)Density: 1.15 g/cm³; (19)Flash Point: 174.6 °C; (20)Enthalpy of Vaporization: 61.14 kJ/mol; (21)Boiling Point: 365.1 °C at 760 mmHg; (22)Vapour Pressure: 1.6E-05 mmHg at 25°C.

Uses of 1-(p-Tolyl)-3-methyl-5-pyrazolone: It can react with acetoacetic acid ethyl ester to produce 3,4-dimethyl-1-p-tolyl-1H-pyrano[2,3-c]pyrazol-6-one. The reaction time is 1 hour with temperature of 150-170°C, and the yield is about 86%.

1-(p-Tolyl)-3-methyl-5-pyrazolone can react with acetoacetic acid ethyl ester to produce 3,4-dimethyl-1-p-tolyl-1H-pyrano[2,3-c]pyrazol-6-one

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1N(/N=C(\C1)C)c2ccc(cc2)C
(2)InChI: InChI=1/C11H12N2O/c1-8-3-5-10(6-4-8)13-11(14)7-9(2)12-13/h3-6H,7H2,1-2H3
(3)InChIKey: IOQOLGUXWSBWHR-UHFFFAOYAE

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rat	LD50	oral	7450mg/kg (7450mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) SKIN AND APPENDAGES (SKIN): HAIR: OTHER	Personal Communication from LONZA Ltd., CH-4002, Basel, SwitzerlandVol. 26APR1982,

Product Name

2,4-Dihydro-5-methyl-2-(4-methylphenyl)-3H-pyrazol-3-one

Synthetic route

1-(p-Tolyl)-3-methyl-5-pyrazolone Consensus Reports

1-(p-Tolyl)-3-methyl-5-pyrazolone Specification

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