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60-80-0 Usage

Chemical Properties

Colorless crystal or white crystalline powder. Soluble in benzene, ethanol, water, chloroform, slightly soluble in ether. Odorless, slightly bitter.

History

Antipyrine (phenazone) was one of the first important synthetic Analgesic drugs that synthesis in Germany in 1884 by a pupil of Emil Fischer.

Uses

Antipyrine has been used for immunoblotting. It has also been used as an internal reference marker for studying the transport characteristics of platinum-containing drug, cisplatin in the human placenta in vitro. Antipyrine is an analgesic and antipyretic that has been given by mouth and as ear drops. It is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver. (From Martindale, The Extra Pharmacopoeia, 30th ed, p29)

Definition

ChEBI: Antipyrine is a pyrazolone derivative that is 1,2-dihydropyrazol-3-one substituted with methyl groups at N-1 and C-5 and with a phenyl group at N-2. It has a role as a non-narcotic analgesic, an antipyretic, a non-steroidal anti-inflammatory drug, a cyclooxygenase 3 inhibitor, a xenobiotic and an environmental contaminant.

Preparation

Antipyrine (1) was prepared from the reaction of 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one with methyl iodide in methanol or in acetonitrile containing sodium bicarbonate in water in 58% yield. The reaction of 1-methyl-2-phenylhydrazine (2) with methyl 3-oxobutanoate (3) in acetonitrile gave 1 and pyrazolone 4 . Krohn has been reported the synthesis of 1 from the reaction of 5 with dimethyl sulfate in 71% yield. The reaction of pyrazolone 6 with methanol in the presence of triphenylphosphine afforded 1 (14%) and pyrazole 7 (53%). The same reaction was reported by Pegurier et al by heating the reactants in methanol containing calcium monoxide. Knorr early reported also, the synthesis of antipyrine from heating of 1-phenyl-5-ethoxy-3- methylpyrazole (8) with methyl iodide in methanol.

Brand name

Aerol;Antigestin;Asthma dellipsoids;Aurafair;Auralgicin;Auraltone;Bajumol;Breezeazy;Calmasmin;Cetussan;Codalgin;Crema antisolar evanescente;Doleron novum;Dolo-med-much;Dol-stop;Kalopsis;Lanceotic;Lavylgan;Mig-antos;Migranin;Natt-lunedon;Neo-felsol;Orecil;Otipyrin;Otosan-sulfan;Otothricinol;Palacaine;Pasta antisola;Pomada heridas;Prednefrin;Prefrin liquifilm;Prefrin z;Priatan;Prophyllen;Remolmed;Salicopil;Sedaural;Sedonan;Shhe 21;Spalt n;Tympagesic;Visublefarite.

World Health Organization (WHO)

Phenazone is a pyrazolone derivative chemically related to aminophenazone. Some regulatory authorities have imposed restrictions on its use on these grounds. However, a recent international study showed no statisticallybased evidence of an association with agranulocytosis or aplastic anaemia. Nor does it share with aminophenazone the propensity to produce potentially carcinogenic nitrosamines.

General Description

Antipyrine is an antipyretic agent used for the symptomatic treatment of acute otitis media, most commonly in combination with benzocaine. One of the earliest widely used analgesics and antipyretics, antipyrine was gradually replaced in common use by other medications including phenacetin (itself later withdrawn because of safety concerns), aspirin, paracetamol and modern NSAIDs such as ibuprofen.

Biochem/physiol Actions

Antipyrine also referred to as phenazone or phenazonum is an anti-inflammatory agent that possesses analgesic, antipyretic and platelet-inhibitory actions.

Safety Profile

A human Doison bv 1 i an unspecified route. Moderately toxic via ingestion, subcutaneous, and intravenous routes. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Purification Methods

Antipyrine crystallises from EtOH/water mixture, *benzene, *benzene/pet ether or hot water (charcoal), and the crystals are dried under a vacuum. [Beilstein 24 H 27, 24 III/IV 75.]

Check Digit Verification of cas no

The CAS Registry Mumber 60-80-0 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 0 respectively; the second part has 2 digits, 8 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 60-80:
(4*6)+(3*0)+(2*8)+(1*0)=40
40 % 10 = 0
So 60-80-0 is a valid CAS Registry Number.
InChI:InChI: 1S/C11H12N2O/c1-9-8-11(14)13(12(9)2)10-6-4-3-5-7-10/h3-8H,1-2H3

60-80-0 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (D1876)  2,3-Dimethyl-1-phenyl-5-pyrazolone  >99.0%(GC)(T)

  • 60-80-0

  • 25g

  • 220.00CNY

  • Detail
  • TCI America

  • (D1876)  2,3-Dimethyl-1-phenyl-5-pyrazolone  >99.0%(GC)(T)

  • 60-80-0

  • 500g

  • 1,390.00CNY

  • Detail
  • Alfa Aesar

  • (A11089)  Antipyrine, 98%   

  • 60-80-0

  • 100g

  • 225.0CNY

  • Detail
  • Alfa Aesar

  • (A11089)  Antipyrine, 98%   

  • 60-80-0

  • 500g

  • 826.0CNY

  • Detail
  • Sigma-Aldrich

  • (P0800000)  Phenazone  European Pharmacopoeia (EP) Reference Standard

  • 60-80-0

  • P0800000

  • 1,880.19CNY

  • Detail
  • USP

  • (1040005)  Antipyrine  United States Pharmacopeia (USP) Reference Standard

  • 60-80-0

  • 1040005-200MG

  • 4,647.24CNY

  • Detail
  • Sigma-Aldrich

  • (A5882)  Antipyrine  analytical standard

  • 60-80-0

  • A5882-25G

  • 122.85CNY

  • Detail
  • Sigma-Aldrich

  • (A5882)  Antipyrine  analytical standard

  • 60-80-0

  • A5882-100G

  • 375.57CNY

  • Detail
  • Sigma-Aldrich

  • (A5882)  Antipyrine  analytical standard

  • 60-80-0

  • A5882-500G

  • 1,125.54CNY

  • Detail
  • Sigma-Aldrich

  • (90567)  Antipyrine  analytical reference material

  • 60-80-0

  • 90567-100MG

  • 732.42CNY

  • Detail

60-80-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name antipyrine

1.2 Other means of identification

Product number -
Other names Anodynin

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:60-80-0 SDS

60-80-0Synthetic route

edaravone
89-25-8

edaravone

dimethyl sulfate
77-78-1

dimethyl sulfate

antipyrine
60-80-0

antipyrine

Conditions
ConditionsYield
at 160℃; for 5h;71%
at 140 - 170℃;
4-(2,3-dimethyl-5-oxo-2,5-dihydro-pyrazol-1-yl)-benzoic acid
948853-49-4

4-(2,3-dimethyl-5-oxo-2,5-dihydro-pyrazol-1-yl)-benzoic acid

antipyrine
60-80-0

antipyrine

Conditions
ConditionsYield
With potassium carbonate In chloroform at 20℃; for 24h; Irradiation; Inert atmosphere;68%
edaravone
89-25-8

edaravone

methyl iodide
74-88-4

methyl iodide

antipyrine
60-80-0

antipyrine

Conditions
ConditionsYield
Stage #1: edaravone; methyl iodide In acetonitrile at 120℃;
Stage #2: With sodium hydrogencarbonate In water; ethyl acetate
58%
With methanol at 100 - 120℃; im Rohr;
With sodium hydrogencarbonate In acetonitrile
In acetonitrile for 12h; Heating; Sealed tube;
methanol
67-56-1

methanol

edaravone
89-25-8

edaravone

A

5-methoxy-3-methyl-1-phenyl-1H-pyrazole
27349-35-5

5-methoxy-3-methyl-1-phenyl-1H-pyrazole

B

antipyrine
60-80-0

antipyrine

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 20h; Ambient temperature;A 53%
B 14%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 20h; Product distribution; Ambient temperature; various solvents, various ratio of products;
3-methyl-1-phenylpyrazolin-5(4H)-one
19735-89-8

3-methyl-1-phenylpyrazolin-5(4H)-one

A

5-methoxy-3-methyl-1-phenyl-1H-pyrazole
27349-35-5

5-methoxy-3-methyl-1-phenyl-1H-pyrazole

B

antipyrine
60-80-0

antipyrine

methanol
67-56-1

methanol

3-methyl-1-phenylpyrazolin-5(4H)-one
19735-89-8

3-methyl-1-phenylpyrazolin-5(4H)-one

antipyrine
60-80-0

antipyrine

Conditions
ConditionsYield
With hydrogenchloride at 120℃;
With ethyl bromide at 120℃;
methyl bromide
74-83-9

methyl bromide

3-methyl-1-phenylpyrazolin-5(4H)-one
19735-89-8

3-methyl-1-phenylpyrazolin-5(4H)-one

antipyrine
60-80-0

antipyrine

Conditions
ConditionsYield
With methoxybenzene
at 132℃;
3-methyl-1-phenylpyrazolin-5(4H)-one
19735-89-8

3-methyl-1-phenylpyrazolin-5(4H)-one

methylene chloride
74-87-3

methylene chloride

antipyrine
60-80-0

antipyrine

Conditions
ConditionsYield
With methylpyridine at 135℃;
With antipyrine at 135℃;
3-methyl-1-phenylpyrazolin-5(4H)-one
19735-89-8

3-methyl-1-phenylpyrazolin-5(4H)-one

methyl p-toluene sulfonate
80-48-8

methyl p-toluene sulfonate

antipyrine
60-80-0

antipyrine

Conditions
ConditionsYield
at 150 - 160℃;
3-methyl-1-phenylpyrazolin-5(4H)-one
19735-89-8

3-methyl-1-phenylpyrazolin-5(4H)-one

dimethyl sulfate
77-78-1

dimethyl sulfate

antipyrine
60-80-0

antipyrine

Conditions
ConditionsYield
With xylene at 150℃;
With calcium oxide In methanol
methanol
67-56-1

methanol

3-methyl-1-phenylpyrazolin-5(4H)-one
19735-89-8

3-methyl-1-phenylpyrazolin-5(4H)-one

methyl iodide
74-88-4

methyl iodide

antipyrine
60-80-0

antipyrine

Conditions
ConditionsYield
at 100 - 120℃; im Rohr;
5-methoxy-3-methyl-1-phenyl-1H-pyrazole
27349-35-5

5-methoxy-3-methyl-1-phenyl-1H-pyrazole

antipyrine
60-80-0

antipyrine

Conditions
ConditionsYield
at 250 - 260℃; im geschlossenen Gefaess;
at 250 - 260℃; im geschlossenen Gefaess;
1-nitro-2-(2-nitrophenyl)benzene
2436-96-6

1-nitro-2-(2-nitrophenyl)benzene

antipyrine
60-80-0

antipyrine

Conditions
ConditionsYield
bei der elektrolytischen Reduktion;
methanol
67-56-1

methanol

5-ethoxy-3-methyl-1-phenyl-1H-pyrazole
1016-41-7

5-ethoxy-3-methyl-1-phenyl-1H-pyrazole

methyl iodide
74-88-4

methyl iodide

antipyrine
60-80-0

antipyrine

Conditions
ConditionsYield
at 115℃; Kochen des Reaktionsprodukts mit Natronlauge;
at 115℃; Kochen des Reaktionsprodukts mit Natronlauge;
2-(5-methyl-2-phenyl-2H-pyrazol-3-yloxy)-ethanol
5372-10-1

2-(5-methyl-2-phenyl-2H-pyrazol-3-yloxy)-ethanol

antipyrine
60-80-0

antipyrine

Conditions
ConditionsYield
bei der Methylierung;
carbonic acid methyl ester-(5-methyl-2-phenyl-2H-pyrazol-3-yl ester)

carbonic acid methyl ester-(5-methyl-2-phenyl-2H-pyrazol-3-yl ester)

A

5-methoxy-3-methyl-1-phenyl-1H-pyrazole
27349-35-5

5-methoxy-3-methyl-1-phenyl-1H-pyrazole

B

antipyrine
60-80-0

antipyrine

Conditions
ConditionsYield
at 200℃;
methylene chloride
74-87-3

methylene chloride

1-benzyl-5-methyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one
55774-20-4

1-benzyl-5-methyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one

A

3-methyl-1-phenylpyrazolin-5(4H)-one
19735-89-8

3-methyl-1-phenylpyrazolin-5(4H)-one

B

antipyrine
60-80-0

antipyrine

C

4-benzyl-5-methyl-2-phenyl-1,2-dihydro-pyrazol-3-one
54462-78-1

4-benzyl-5-methyl-2-phenyl-1,2-dihydro-pyrazol-3-one

Conditions
ConditionsYield
at 150 - 180℃;
antipyric acid
83-10-3

antipyric acid

antipyrine
60-80-0

antipyrine

Conditions
ConditionsYield
Beim Erhitzen ueber den Schmelzpunkt;
2,2'-Bis-(N'-acetyl-hydrazino)-biphenyl

2,2'-Bis-(N'-acetyl-hydrazino)-biphenyl

A

acetamide
60-35-5

acetamide

B

antipyrine
60-80-0

antipyrine

Conditions
ConditionsYield
at 250 - 260℃;
ethyl acetoacetate
141-97-9

ethyl acetoacetate

1-Methyl-1-phenylhydrazine
618-40-6

1-Methyl-1-phenylhydrazine

antipyrine
60-80-0

antipyrine

Conditions
ConditionsYield
at 130 - 160℃;
ethyl acetoacetate
141-97-9

ethyl acetoacetate

2-methylphenylhydrazine
529-27-1

2-methylphenylhydrazine

antipyrine
60-80-0

antipyrine

Conditions
ConditionsYield
at 130 - 160℃;
3-benzoyloxy-1,5-dimethyl-2-phenyl-pyrazolium; chloride

3-benzoyloxy-1,5-dimethyl-2-phenyl-pyrazolium; chloride

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

antipyrine
60-80-0

antipyrine

3-benzoyloxy-1,5-dimethyl-2-phenyl-pyrazolium; chloride

3-benzoyloxy-1,5-dimethyl-2-phenyl-pyrazolium; chloride

A

antipyrine
60-80-0

antipyrine

B

methylene chloride
74-87-3

methylene chloride

C

(3-methyl-1-phenyl-1H-pyrazol-5-yl) benzoate
56159-67-2

(3-methyl-1-phenyl-1H-pyrazol-5-yl) benzoate

D

benzoyl chloride
98-88-4

benzoyl chloride

Conditions
ConditionsYield
at 180℃;
methylene chloride
74-87-3

methylene chloride

edaravone
89-25-8

edaravone

antipyrine
60-80-0

antipyrine

Conditions
ConditionsYield
With methanol at 95 - 100℃; under 6840 - 7600 Torr;
2,2'-azinobis(3-ethylbenzthiazolinesulfonate)
28752-68-3

2,2'-azinobis(3-ethylbenzthiazolinesulfonate)

1,5-Dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one
60-80-0

1,5-Dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one

A

antipyrine
60-80-0

antipyrine

B

C18H18N4O6S4(1+)
28752-68-3

C18H18N4O6S4(1+)

Conditions
ConditionsYield
Rate constant;
(±)-2-chloro-10-(3-dimethylamino-2-methylpropyl)phenothiazine
20828-91-5

(±)-2-chloro-10-(3-dimethylamino-2-methylpropyl)phenothiazine

1,5-Dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one
60-80-0

1,5-Dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one

A

antipyrine
60-80-0

antipyrine

B

trimeprazine(1+) radical
20828-91-5

trimeprazine(1+) radical

Conditions
ConditionsYield
Rate constant; pH 3;
4-formyl-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one
950-81-2

4-formyl-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one

3-amino crotonic acid-tert-butylester
16052-66-7

3-amino crotonic acid-tert-butylester

A

antipyrine
60-80-0

antipyrine

B

di-tert-butyl 2,6-dimethylpyridine-3,5-dicarboxylate
55536-75-9

di-tert-butyl 2,6-dimethylpyridine-3,5-dicarboxylate

Conditions
ConditionsYield
With pyridine; thionyl chloride 1.) CH2Cl2, from 0 deg C to 20 deg C, 1 h, 2.) CH2Cl2, 20 deg C, 18 h; Multistep reaction;
4-formyl-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one
950-81-2

4-formyl-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one

ethyl (Z)-3-amino-3-phenylacrylate
53256-19-2

ethyl (Z)-3-amino-3-phenylacrylate

A

antipyrine
60-80-0

antipyrine

B

diethyl 2,6-diphenyl-3,5-pyridinedicarboxylate

diethyl 2,6-diphenyl-3,5-pyridinedicarboxylate

Conditions
ConditionsYield
With pyridine; thionyl chloride 1.) CH2Cl2, from 0 deg C to 20 deg C, 1 h, 2.) CH2Cl2, 20 deg C, 18 h; Multistep reaction;
4-formyl-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one
950-81-2

4-formyl-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one

methyl 3-aminocrotonate
21731-17-9

methyl 3-aminocrotonate

A

antipyrine
60-80-0

antipyrine

B

dimethyl 2,6-dimethylpyridine-3,5-dicarboxylate
27525-74-2

dimethyl 2,6-dimethylpyridine-3,5-dicarboxylate

Conditions
ConditionsYield
With pyridine; thionyl chloride 1.) CH2Cl2, from 0 deg C to 20 deg C, 1 h, 2.) CH2Cl2, 20 deg C, 18 h; Multistep reaction;
4-formyl-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one
950-81-2

4-formyl-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one

ethyl 3-aminobut-2-enoate
626-34-6

ethyl 3-aminobut-2-enoate

A

antipyrine
60-80-0

antipyrine

B

2,6-dimethyl-pyridine-3,5-dicarboxylic acid diethyl ester
1149-24-2

2,6-dimethyl-pyridine-3,5-dicarboxylic acid diethyl ester

Conditions
ConditionsYield
With pyridine; thionyl chloride 1.) CH2Cl2, from 0 deg C to 20 deg C, 1 h, 2.) CH2Cl2, 20 deg C, 18 h; Multistep reaction;
antipyrine
60-80-0

antipyrine

Hexafluoroacetone
684-16-2

Hexafluoroacetone

4-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluorethyl)-2,3-dimethyl-1-phenylpyrazol-5-one

4-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluorethyl)-2,3-dimethyl-1-phenylpyrazol-5-one

Conditions
ConditionsYield
In chloroform 1.) 20 deg C, 24 h, 2.) 75 deg C, 3 h;100%
antipyrine
60-80-0

antipyrine

antipyrine perchlorate
20776-03-8, 49727-60-8

antipyrine perchlorate

Conditions
ConditionsYield
With perchloric acid In ethanol100%
antipyrine
60-80-0

antipyrine

2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

bis[1-(2,3-dimethyl-1-phenyl-3-pyrazolin-5-one)]-2-nitrophenylmethane
14957-18-7

bis[1-(2,3-dimethyl-1-phenyl-3-pyrazolin-5-one)]-2-nitrophenylmethane

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 20℃; for 1h;99%
With hydrogenchloride In methanol at 60℃; for 12h;67%
With ethanol hydrochloride
antipyrine
60-80-0

antipyrine

rac-1-(4-methoxyphenyl)-ethanol
3319-15-1

rac-1-(4-methoxyphenyl)-ethanol

4-[1-(4-methoxyphenyl)ethyl]antipyrine
1321804-59-4

4-[1-(4-methoxyphenyl)ethyl]antipyrine

Conditions
ConditionsYield
With gluconic acid In water at 100℃; for 4h;99%
antipyrine
60-80-0

antipyrine

2,3,4,9-tetrahydro-9-(2-hydroxy-4,4-dimethyl-6-oxo-1-cyclohexen-1-yl)-3,3-dimethyl-1H-xanthen-1-one
19744-87-7

2,3,4,9-tetrahydro-9-(2-hydroxy-4,4-dimethyl-6-oxo-1-cyclohexen-1-yl)-3,3-dimethyl-1H-xanthen-1-one

4-(3,3-dimethyl-1-oxo-2,3,4,9-tetrahydro-1H-xanthen-9-yl)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

4-(3,3-dimethyl-1-oxo-2,3,4,9-tetrahydro-1H-xanthen-9-yl)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

Conditions
ConditionsYield
With iron(III) chloride; triphenylphosphine In 1,2-dichloro-ethane at 80℃; for 11h;99%
antipyrine
60-80-0

antipyrine

salicylaldehyde
90-02-8

salicylaldehyde

dimedone
126-81-8

dimedone

4-(3,3-dimethyl-1-oxo-2,3,4,9-tetrahydro-1H-xanthen-9-yl)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

4-(3,3-dimethyl-1-oxo-2,3,4,9-tetrahydro-1H-xanthen-9-yl)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

Conditions
ConditionsYield
With iron(III) chloride; triphenylphosphine In nitromethane at 100℃; for 11h;99%
antipyrine
60-80-0

antipyrine

di(p-tolyl) disulfide
103-19-5

di(p-tolyl) disulfide

1,5-dimethyl-2-phenyl-4-(p-tolylthio)-1,2-dihydro-3H-pyrazol-3-one

1,5-dimethyl-2-phenyl-4-(p-tolylthio)-1,2-dihydro-3H-pyrazol-3-one

Conditions
ConditionsYield
With dipotassium peroxodisulfate; potassium iodide In acetonitrile at 60℃; for 16h;99%
With 1,4-diaza-bicyclo[2.2.2]octane; silver(I) acetate In methanol at 20℃; for 2h; Catalytic behavior; Reagent/catalyst; Solvent; Sealed tube;98%
With silver(I) acetate; silver trifluoromethanesulfonate In toluene at 100℃; for 16h; Temperature; Reagent/catalyst; Inert atmosphere;76%
antipyrine
60-80-0

antipyrine

bis(2-benzoylaminophenyl) disulfide
135-57-9

bis(2-benzoylaminophenyl) disulfide

N-(2-((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)thio)phenyl)benzamide

N-(2-((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)thio)phenyl)benzamide

Conditions
ConditionsYield
With dipotassium peroxodisulfate; potassium iodide In acetonitrile at 60℃; for 16h;99%
With 1,4-diaza-bicyclo[2.2.2]octane; silver(I) acetate In methanol at 20℃; for 2h; Sealed tube;81%
antipyrine
60-80-0

antipyrine

diphenyldisulfane
882-33-7

diphenyldisulfane

1,5-dimethyl-2-phenyl-4-(phenylthio)-1,2-dihydro-3H-pyrazol-3-one

1,5-dimethyl-2-phenyl-4-(phenylthio)-1,2-dihydro-3H-pyrazol-3-one

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; silver(I) acetate In methanol at 20℃; Sealed tube;99%
With dipotassium peroxodisulfate; potassium iodide In acetonitrile at 60℃; for 16h; Reagent/catalyst; Solvent; Temperature;99%
antipyrine
60-80-0

antipyrine

N-(4,4-diethoxybutyl)ethenesulfonamide

N-(4,4-diethoxybutyl)ethenesulfonamide

1,5-dimethyl-2-phenyl-4-(1-(vinylsulfonyl)pyrrolidin-2-yl)-1,2-dihydro-3H-pyrazol-3-one

1,5-dimethyl-2-phenyl-4-(1-(vinylsulfonyl)pyrrolidin-2-yl)-1,2-dihydro-3H-pyrazol-3-one

Conditions
ConditionsYield
With trifluoroacetic acid In benzene for 5h; Reflux;99%
antipyrine
60-80-0

antipyrine

methyl 3,3,3-trifluoropyruvate
13089-11-7

methyl 3,3,3-trifluoropyruvate

4-(1-hydroxy-1-methoxycarbonyl-2,2,2-trifluoroethyl)-2,3-dimethyl-1-phenylpyrazol-5-one

4-(1-hydroxy-1-methoxycarbonyl-2,2,2-trifluoroethyl)-2,3-dimethyl-1-phenylpyrazol-5-one

Conditions
ConditionsYield
In chloroform 1.) 20 deg C, 16 h, 2.) reflux, 2 h;98%
antipyrine
60-80-0

antipyrine

(2-Methylthio-2-pyrrolidinovinyl)phenylketon
185245-63-0

(2-Methylthio-2-pyrrolidinovinyl)phenylketon

1,2-dihydro-1-methyl-2,4-diphenyl-6-(1-pyrrolidyl)-3H-indazol-3-one

1,2-dihydro-1-methyl-2,4-diphenyl-6-(1-pyrrolidyl)-3H-indazol-3-one

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran; diethyl ether -78 deg C, 30-40 min; RT, 6-8 h;98%
antipyrine
60-80-0

antipyrine

4,4'-dimethoxyphenyl disulfide
5335-87-5

4,4'-dimethoxyphenyl disulfide

4-((4-methoxyphenyl)thio)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one

4-((4-methoxyphenyl)thio)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one

Conditions
ConditionsYield
With dipotassium peroxodisulfate; potassium iodide In acetonitrile at 60℃; for 16h;98%
With 1,4-diaza-bicyclo[2.2.2]octane; silver(I) acetate In methanol at 20℃; for 2h; Sealed tube;86%
2-thienyl disulfide
6911-51-9

2-thienyl disulfide

antipyrine
60-80-0

antipyrine

1,5-dimethyl-2-phenyl-4-(thiophen-2-ylthio)-1,2-dihydro-3H-pyrazol-3-one

1,5-dimethyl-2-phenyl-4-(thiophen-2-ylthio)-1,2-dihydro-3H-pyrazol-3-one

Conditions
ConditionsYield
With dipotassium peroxodisulfate; potassium iodide In acetonitrile at 60℃; for 16h;98%
With 1,4-diaza-bicyclo[2.2.2]octane; silver(I) acetate In methanol at 20℃; for 2h; Sealed tube;83%
ammonium thiocyanate

ammonium thiocyanate

antipyrine
60-80-0

antipyrine

1,5-dimethyl-2-phenyl-4-thiocyanato-1,2-dihydro-3H-pyrazol-3-one
91397-05-6

1,5-dimethyl-2-phenyl-4-thiocyanato-1,2-dihydro-3H-pyrazol-3-one

Conditions
ConditionsYield
With dipotassium peroxodisulfate In acetonitrile at 20℃; for 16h; Reagent/catalyst;98%
antipyrine
60-80-0

antipyrine

para-nitrophenyl bromide
586-78-7

para-nitrophenyl bromide

1,5-dimethyl-4-(4-nitrophenyl)-2-phenyl-1H-pyrazol-3(2H)-one

1,5-dimethyl-4-(4-nitrophenyl)-2-phenyl-1H-pyrazol-3(2H)-one

Conditions
ConditionsYield
With potassium acetate; palladium diacetate at 150℃; for 16h; Inert atmosphere; Schlenk technique;98%
1-oxothiolane
1600-44-8

1-oxothiolane

antipyrine
60-80-0

antipyrine

(2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)-tetrahydrothiopheniumperchlorat

(2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)-tetrahydrothiopheniumperchlorat

Conditions
ConditionsYield
With lithium perchlorate; trifluoroacetic acid In dichloromethane 2.) r.t.;97%
antipyrine
60-80-0

antipyrine

di(benzothiazol-2-yl)disulfide
120-78-5

di(benzothiazol-2-yl)disulfide

4-(benzo[d]thiazol-2-ylthio)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one

4-(benzo[d]thiazol-2-ylthio)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one

Conditions
ConditionsYield
With dipotassium peroxodisulfate; potassium iodide In acetonitrile at 60℃; for 16h;97%
With 1,4-diaza-bicyclo[2.2.2]octane; silver(I) acetate In methanol at 20℃; for 2h; Sealed tube;84%
antipyrine
60-80-0

antipyrine

2-bromo-6-(trifluoromethyl)pyridine
189278-27-1

2-bromo-6-(trifluoromethyl)pyridine

1,5-dimethyl-2-phenyl-4-(6-(trifluoromethyl)pyridin-2-yl)-1H-pyrazol-3(2H)-one

1,5-dimethyl-2-phenyl-4-(6-(trifluoromethyl)pyridin-2-yl)-1H-pyrazol-3(2H)-one

Conditions
ConditionsYield
With potassium acetate; palladium diacetate at 150℃; for 16h; Inert atmosphere; Schlenk technique;97%
4-(morpholinomethyl)morpholine
5625-90-1

4-(morpholinomethyl)morpholine

antipyrine
60-80-0

antipyrine

4-(N-morpholinylmethyl) antipyrine
101268-93-3

4-(N-morpholinylmethyl) antipyrine

Conditions
ConditionsYield
In acetonitrile at 40℃; for 24h;95%
With water
antipyrine
60-80-0

antipyrine

4,4'-dichlorodiphenyl disulfide
1142-19-4

4,4'-dichlorodiphenyl disulfide

4-((4-chlorophenyl)thio)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one

4-((4-chlorophenyl)thio)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one

Conditions
ConditionsYield
With dipotassium peroxodisulfate; potassium iodide In acetonitrile at 60℃; for 16h;95%
With 1,4-diaza-bicyclo[2.2.2]octane; silver(I) acetate In methanol at 20℃; for 2h; Sealed tube;83%
antipyrine
60-80-0

antipyrine

iodoantipyrine
129-81-7

iodoantipyrine

Conditions
ConditionsYield
With [bis(pyridine)iodine]+ tetrafluoroborate In dichloromethane for 2h; Ambient temperature;94%
With iodine; oxygen; 9,10-phenanthrenequinone; trifluoroacetic acid In 1,2-dichloro-ethane at 25℃; for 1h; Irradiation; regioselective reaction;83%
With iodine In dichloromethane at 20℃; for 2h;83%
antipyrine
60-80-0

antipyrine

di(p-tolyl) disulfide
103-19-5

di(p-tolyl) disulfide

1,5-dimethyl-2-phenyl-4-(phenylthio)-1,2-dihydro-3H-pyrazol-3-one

1,5-dimethyl-2-phenyl-4-(phenylthio)-1,2-dihydro-3H-pyrazol-3-one

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; silver(I) acetate In methanol at 20℃; for 2h; Sealed tube;94%
antipyrine
60-80-0

antipyrine

3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

bis[1-(2,3-dimethyl-1-phenyl-3-pyrazolin-5-one)]-3-nitrophenylmethane
1606-53-7

bis[1-(2,3-dimethyl-1-phenyl-3-pyrazolin-5-one)]-3-nitrophenylmethane

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 20℃; for 24h;93%
With hydrogenchloride
With sulfuric acid
antipyrine
60-80-0

antipyrine

2-(4-bromo-benzylidenamino)-ethanol
27895-60-9

2-(4-bromo-benzylidenamino)-ethanol

4-[(4-Bromo-phenyl)-(2-hydroxy-ethylamino)-methyl]-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one
84905-11-3

4-[(4-Bromo-phenyl)-(2-hydroxy-ethylamino)-methyl]-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 12h; Heating;93%
antipyrine
60-80-0

antipyrine

2-[(4-chlorophenyl)(phenylthio)methyl]-3-hydroxy-5,5-dimethylcyclohex-2-enone
1609076-47-2

2-[(4-chlorophenyl)(phenylthio)methyl]-3-hydroxy-5,5-dimethylcyclohex-2-enone

4-[(4-chlorophenyl)(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)methyl]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one
1609076-74-5

4-[(4-chlorophenyl)(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)methyl]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

Conditions
ConditionsYield
With manganese(II) chloride tetrahydrate In nitromethane at 100℃; for 6h;93%
bromochlorobenzene
106-39-8

bromochlorobenzene

antipyrine
60-80-0

antipyrine

4-(4-chlorophenyl)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

4-(4-chlorophenyl)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

Conditions
ConditionsYield
With potassium acetate; palladium diacetate at 150℃; for 16h; Inert atmosphere; Schlenk technique;93%
antipyrine
60-80-0

antipyrine

1,2-bis(3,5-dichlorophenyl)disulfane
137897-99-5

1,2-bis(3,5-dichlorophenyl)disulfane

4-((3,5-dichlorophenyl)thio)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one

4-((3,5-dichlorophenyl)thio)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one

Conditions
ConditionsYield
With dipotassium peroxodisulfate; potassium iodide In acetonitrile at 60℃; for 16h;92%
With 1,4-diaza-bicyclo[2.2.2]octane; silver(I) acetate In methanol at 20℃; for 8h; Sealed tube;49%
2-(p-Nitrobenzylidenamino)ethanol
19394-08-2

2-(p-Nitrobenzylidenamino)ethanol

antipyrine
60-80-0

antipyrine

4-[(2-Hydroxy-ethylamino)-(4-nitro-phenyl)-methyl]-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one
84905-12-4

4-[(2-Hydroxy-ethylamino)-(4-nitro-phenyl)-methyl]-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 12h; Heating;91%
antipyrine
60-80-0

antipyrine

potassium thioacyanate
333-20-0

potassium thioacyanate

1,5-dimethyl-2-phenyl-4-thiocyanato-1,2-dihydro-3H-pyrazol-3-one
91397-05-6

1,5-dimethyl-2-phenyl-4-thiocyanato-1,2-dihydro-3H-pyrazol-3-one

Conditions
ConditionsYield
With dipotassium peroxodisulfate In acetonitrile at 20℃; for 16h; Reagent/catalyst;90%
With bromine; acetic acid

60-80-0Relevant articles and documents

-

Gosztonyi

, p. 196 (1969)

-

Metal-Free Direct C–H Thiolation and Thiocyanation of Pyrazolones

Kittikool, Tanakorn,Yotphan, Sirilata

supporting information, (2020/02/13)

Metal-free approach for direct C–H thiolation and thiocyanation of N-substituted pyrazolones with disulfides and thiocyanate salts, respectively, are developed. These reactions allow the C–S bond coupling to proceed effectively under mild conditions, providing useful and convenient methods for preparation of a series of 4-thio-substituted pyrazolone analogues, which have potential applications in organic, medicinal and material chemistry. Preliminary mechanistic investigation suggested that radical processes are likely to involve in these transformations.

Copper-catalyzed acylation of pyrazolones with aldehydes to afford 4-acylpyrazolones

Xiao, Yan,Wu, Xiaopeng,Teng, Jiangang,Sun, Song,Yu, Jin-Tao,Cheng, Jiang

supporting information, p. 7552 - 7557 (2019/08/20)

Copper-catalyzed direct acylation of the alkenyl C-H bond in 1,2-dihydro-3H-pyrazol-3-ones has been developed, affording a series of 4-acylpyrazolones in moderate to good yields. Notably, this protocol involves readily accessible substrates and reagents, which have good functional group tolerance leading to pyrazolone derivatives under mild reaction conditions.

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