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89-25-8

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89-25-8 Usage

Description

Different sources of media describe the Description of 89-25-8 differently. You can refer to the following data:
1. Edaravone was marketed in Japan for improving neurologic recovery following acute brain infarction. Currently, several agents classified as neuroprotectants and acting by diverse mechanisms (inhibition of glutamate release, blockade of calcium channels, lazaroids) have been marketed for treating the outcomes of brain damage due to trauma, ischemia or cardiac arrest. Edavarone is the first antioxidant with free radical scavenging activity to be introduced for this pathology. This previously described molecule (in particular as norantipyrine, one of three metabolites of antipyrine in mammals) can be simply prepared by direct cyclization of phenylhydrazine with alkylacetoacetate. Edarevone is a lipophilic agent, readily accessible to brain tissue, that is capable of reducing edema in the brain following ischemia by blocking the arachidonic acid cascade triggering peroxidative neurodegeneration. Interestingly, this agent has been shown to quench active oxygen species in endothelial cell homogenate, as well as inhibiting in vitro lipid peroxidative disintegration of membranes, so making this compound effective during reperfusion following ischemic injury. As an additional indication, phase III trials started with edaravone for increasing the chance of recovery after subarachnoid hemorrhage.
2. MCI-186 is a free radical scavenger with diverse protective effects in vivo. Most notably, it reduces damage due to ischemia-reperfusion injury in lung, liver, and brain in animal models of transplant, infection, traumatic brain injury, and stroke. MCI-186 provides these protective effects, at least in part, by reducing reactive oxygen species, inhibiting apoptosis, and blocking nonenzymatic peroxidation and lipoxygenase activity.

Chemical Properties

Off white to light yellow powder

Originator

Mitsubishi Pharma (Japan)

Uses

Different sources of media describe the Uses of 89-25-8 differently. You can refer to the following data:
1. 3-Methyl-1-phenyl-2-pyrazolin-5-one used as reagent for detection of reducing carbohydrates by ESI/MALDI -MS.
2. antioxidant, lipoxygenase inhibitor
3. Edaravone inhibits the disease activity in rheumatoid arthritis.

Definition

ChEBI: A pyrazolone that is 2,4-dihydro-3H-pyrazol-3-one which is substituted at positions 2 and 5 by phenyl and methyl groups, respectively.

Brand name

Radicut

General Description

A free radical scavenger and antioxidant that reduces post-ischemic brain injury. Inhibits iron-dependent peroxidation in rat brain homogenates (IC50 = 15 μM). Inhibits mitochondrial permeability transition pore.

Hazard

Toxic by ingestion.

Flammability and Explosibility

Notclassified

Biological Activity

A radical scavenger and antioxidant which is able to protect against the effects of ischemia, probably by inhibiting the lipoxygenase system. Protects against MPTP-induced neurotoxicity.

Biochem/physiol Actions

Product does not compete with ATP.

Safety Profile

Moderately toxic by ingestion andintraperitoneal routes. An eye irritant. When heated todecomposition it emits toxic fumes of NOx.

Purification Methods

Crystallise the pyrazolone from hot H2O, EtOH or EtOH/water (1:1). It complexes with metals. [Veibel et al. Acta Chim Scand 6 1066 1952, Beilstein 24 II 9, 24 III/IV 71.]

References

1) Watanabe et al. (1994), Protective effects of MCI-186 on cerebral ischemia:possible involvement of free radical scavenging and antioxidant actions; J. Pharmacol. Exp. Ther., 268 1597 2) Yoshida et al. (2006) Neuroprotective effects of edaravone:a novel free radical scavenger in cerebrovascular injury; CNS Drug Reviews, 12 9 3) Kawasaki et al. (2007) Edaravone (3-Methyl-1-phenyl-2-pyrazolin-5-one), a Radical Scavenger, Prevents 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced Neurotoxicity in the Substantia Nigra but Not the Striatum; J. Pharmacol. Exp. Ther., 322 274

Check Digit Verification of cas no

The CAS Registry Mumber 89-25-8 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 9 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 89-25:
(4*8)+(3*9)+(2*2)+(1*5)=68
68 % 10 = 8
So 89-25-8 is a valid CAS Registry Number.
InChI:InChI=1/C10H10N2O/c1-8-7-10(13)12(11-8)9-5-3-2-4-6-9/h2-6H,7H2,1H3

89-25-8 Well-known Company Product Price

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

  • (M0687)  3-Methyl-1-phenyl-5-pyrazolone  >98.0%(HPLC)(T)

  • 89-25-8

  • 25g

  • 160.00CNY

  • Detail
  • TCI America

  • (M0687)  3-Methyl-1-phenyl-5-pyrazolone  >98.0%(HPLC)(T)

  • 89-25-8

  • 500g

  • 575.00CNY

  • Detail
  • Alfa Aesar

  • (A11161)  3-Methyl-1-phenyl-2-pyrazolin-5-one, 98+%   

  • 89-25-8

  • 100g

  • 203.0CNY

  • Detail
  • Alfa Aesar

  • (A11161)  3-Methyl-1-phenyl-2-pyrazolin-5-one, 98+%   

  • 89-25-8

  • 500g

  • 417.0CNY

  • Detail
  • Alfa Aesar

  • (A11161)  3-Methyl-1-phenyl-2-pyrazolin-5-one, 98+%   

  • 89-25-8

  • 2500g

  • 1790.0CNY

  • Detail
  • Aldrich

  • (M70800)  3-Methyl-1-phenyl-2-pyrazoline-5-one  99%

  • 89-25-8

  • M70800-5G

  • 245.70CNY

  • Detail
  • Aldrich

  • (M70800)  3-Methyl-1-phenyl-2-pyrazoline-5-one  99%

  • 89-25-8

  • M70800-100G

  • 266.76CNY

  • Detail
  • Aldrich

  • (M70800)  3-Methyl-1-phenyl-2-pyrazoline-5-one  99%

  • 89-25-8

  • M70800-500G

  • 519.48CNY

  • Detail
  • Sigma-Aldrich

  • (Y0001138)  PhenazoneimpurityA  European Pharmacopoeia (EP) Reference Standard

  • 89-25-8

  • Y0001138

  • 1,880.19CNY

  • Detail
  • USP

  • (1040016)  AntipyrineRelatedCompoundA  United States Pharmacopeia (USP) Reference Standard

  • 89-25-8

  • 1040016-25MG

  • 14,500.98CNY

  • Detail

89-25-8SDS

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 edaravone

1.2 Other means of identification

Product number -
Other names 3-METHYL-1-PHENYL-2-PYRAZOLIN-5-ON

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:89-25-8 SDS

89-25-8Synthetic route

ethyl acetoacetate
141-97-9

ethyl acetoacetate

phenylhydrazine
100-63-0

phenylhydrazine

edaravone
89-25-8

edaravone

Conditions
ConditionsYield
In acetic acid Heating;100%
for 0.166667h; Irradiation;100%
at 0 - 90℃; for 1.5h;100%
acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

phenylhydrazine
100-63-0

phenylhydrazine

edaravone
89-25-8

edaravone

Conditions
ConditionsYield
With acetic acid for 3h; Reflux;98%
With cellulose sulfuric acid In water at 20℃; for 0.133333h; Knorr Pyrazole Synthesis; Green chemistry; regioselective reaction;92%
With Fe3O4(at)SiO2-bonded N-propyl-diethylenetetrasulfamic acid In water at 20℃; for 0.416667h; Catalytic behavior; Green chemistry;82%
4-methyleneoxetan-2-one
674-82-8

4-methyleneoxetan-2-one

phenylhydrazine
100-63-0

phenylhydrazine

edaravone
89-25-8

edaravone

Conditions
ConditionsYield
Stage #1: 4-methyleneoxetan-2-one With ammonium hydroxide at 10℃; for 0.5h;
Stage #2: phenylhydrazine at 60℃; for 2h;
Stage #3: With hydrogenchloride In water for 1h; pH=5;
93%
5-methyl-2-phenylpyrazolidin-3-one
13292-56-3

5-methyl-2-phenylpyrazolidin-3-one

edaravone
89-25-8

edaravone

Conditions
ConditionsYield
With sodium anthraquinone-2-sulfonate; palladium diacetate; potassium carbonate In chlorobenzene at 110℃; for 6h; Reagent/catalyst;92%
N-acetoacetylphenylhydroxyloamine
27991-08-8

N-acetoacetylphenylhydroxyloamine

A

N-Phenylhydroxylamine
100-65-2

N-Phenylhydroxylamine

B

edaravone
89-25-8

edaravone

Conditions
ConditionsYield
With phenylhydrazine In chloroform for 3h; Ambient temperature;A 90%
B 81%
phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

ethyl acetoacetate
141-97-9

ethyl acetoacetate

edaravone
89-25-8

edaravone

Conditions
ConditionsYield
In ethanol at 75℃; for 7h;85%
In ethanol at 50 - 70℃; for 5h; Reflux;85%
With ammonia at 95℃; for 6h; pH=6;85%
phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

ethyl acetoacetate
141-97-9

ethyl acetoacetate

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

A

edaravone
89-25-8

edaravone

B

4,4-methine-bis-(3-methyl-1-phenyl-2-pyrazolin-5-one)
61466-03-3, 4174-09-8

4,4-methine-bis-(3-methyl-1-phenyl-2-pyrazolin-5-one)

Conditions
ConditionsYield
With p-toluenesulfonic acid monohydrate at 110℃; for 1h; Kinetics; Reagent/catalyst; Temperature;A 78%
B 12%
With pyridine hydrochloride at 140℃; for 24h; Kinetics; Reagent/catalyst;A 39%
B 47%
5-isopropoxy-3-methyl-1-phenyl-1H-pyrazole

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

edaravone
89-25-8

edaravone

Conditions
ConditionsYield
With hydrogen bromide; acetic acid at 140℃; for 2h; Inert atmosphere;76%
carbon monoxide
201230-82-2

carbon monoxide

chloroacetone
78-95-5

chloroacetone

phenylhydrazine
100-63-0

phenylhydrazine

edaravone
89-25-8

edaravone

Conditions
ConditionsYield
With palladium diacetate; triethylamine; triphenylphosphine In tetrahydrofuran at 110℃; under 20521.4 Torr; for 10h; Temperature; Reagent/catalyst; Solvent; Time; Autoclave; regioselective reaction;72%
ethyl acetoacetate
141-97-9

ethyl acetoacetate

edaravone
89-25-8

edaravone

Conditions
ConditionsYield
With phenylhydrazine In ethanol67%
With phenylhydrazine In 1,4-dioxane; water11.17 g (64%)
tert-butyl acetoacetate
1694-31-1

tert-butyl acetoacetate

phenylhydrazine
100-63-0

phenylhydrazine

edaravone
89-25-8

edaravone

Conditions
ConditionsYield
In ethanol at 50 - 80℃; for 7h; Temperature; Darkness;60.98%
3-Methyl-1-phenyl-2-pyrazoline-4,5-dione
881-05-0

3-Methyl-1-phenyl-2-pyrazoline-4,5-dione

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

malononitrile
109-77-3

malononitrile

A

bis-p-(N,N-dimethylaminophenyl)malonitrile
27781-29-9

bis-p-(N,N-dimethylaminophenyl)malonitrile

B

edaravone
89-25-8

edaravone

Conditions
ConditionsYield
In ethanol for 2h; Heating;A 60%
B n/a
5-(fluoro-dimethylsilanyl)-3-methyl-1-phenyl-1H-pyrazole
387353-94-8

5-(fluoro-dimethylsilanyl)-3-methyl-1-phenyl-1H-pyrazole

edaravone
89-25-8

edaravone

Conditions
ConditionsYield
With potassium fluoride; 3-chloro-benzenecarboperoxoic acid In N,N-dimethyl-formamide at -100℃;58%
3-Methyl-1-phenyl-2-pyrazoline-4,5-dione
881-05-0

3-Methyl-1-phenyl-2-pyrazoline-4,5-dione

N,N-diethylaniline
91-66-7

N,N-diethylaniline

malononitrile
109-77-3

malononitrile

A

bis-p-(N,N-diethylaminophenyl)malonitrile
27781-21-1

bis-p-(N,N-diethylaminophenyl)malonitrile

B

edaravone
89-25-8

edaravone

Conditions
ConditionsYield
In ethanol for 2h; Heating;A 55%
B 42%
(4E)-4-benzylidene-5-methyl-2-phenyl-3,4-dihydropyrazol-3(3H)-one
130691-00-8

(4E)-4-benzylidene-5-methyl-2-phenyl-3,4-dihydropyrazol-3(3H)-one

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

A

2-Phenylbenzothiazole
883-93-2

2-Phenylbenzothiazole

B

edaravone
89-25-8

edaravone

C

4-phenyl-3-methyl-1-phenylpyrazolo[3,4-b][1,5]benzothiazepine

4-phenyl-3-methyl-1-phenylpyrazolo[3,4-b][1,5]benzothiazepine

Conditions
ConditionsYield
With acetic acid In ethanol for 3h; Heating;A 25%
B n/a
C 55%
formaldehyd
50-00-0

formaldehyd

1-Methoxymethyl-5-methyl-2-phenyl-1,2-dihydro-pyrazol-3-one
98395-57-4

1-Methoxymethyl-5-methyl-2-phenyl-1,2-dihydro-pyrazol-3-one

A

C21H20N4O2
98395-58-5

C21H20N4O2

B

edaravone
89-25-8

edaravone

Conditions
ConditionsYield
With hydrogenchloride In methanol for 0.166667h; Heating;A 53%
B 46%
1-Methoxymethyl-5-methyl-2-phenyl-1,2-dihydro-pyrazol-3-one
98395-57-4

1-Methoxymethyl-5-methyl-2-phenyl-1,2-dihydro-pyrazol-3-one

A

C21H20N4O2
98395-58-5

C21H20N4O2

B

edaravone
89-25-8

edaravone

Conditions
ConditionsYield
With hydrogenchloride In methanol for 0.166667h; Heating;A 53%
B 46%
3-phenylaminobut-2-enoic acid ethyl ester
6287-35-0, 17469-23-7, 66558-23-4

3-phenylaminobut-2-enoic acid ethyl ester

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

edaravone
89-25-8

edaravone

Conditions
ConditionsYield
With potassium acetate In ethanol at 25℃; for 1h;50%
(E)-4-(4-chlorobenzylidene)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one
897030-44-3

(E)-4-(4-chlorobenzylidene)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

A

2-(4-chlorophenyl)benzothiazole
6265-91-4

2-(4-chlorophenyl)benzothiazole

B

edaravone
89-25-8

edaravone

C

4-(4-chlorophenyl)-3-methyl-1-phenylpyrazolo[3,4-b][1,5]benzothiazepine

4-(4-chlorophenyl)-3-methyl-1-phenylpyrazolo[3,4-b][1,5]benzothiazepine

Conditions
ConditionsYield
With acetic acid In ethanol for 3h; Heating;A 20%
B n/a
C 50%
polymer, product of polymerization of 4-vinylbenzyl-polytetrahydrofuran with styrene and 1,4-bis(4-vinylphenoxy)butane, with polytetrahydrofuran chain terminated with 2-phenylhydrazonopropylcarbonyloxy group

polymer, product of polymerization of 4-vinylbenzyl-polytetrahydrofuran with styrene and 1,4-bis(4-vinylphenoxy)butane, with polytetrahydrofuran chain terminated with 2-phenylhydrazonopropylcarbonyloxy group

edaravone
89-25-8

edaravone

Conditions
ConditionsYield
With trifluoroacetic acid In acetonitrile at 20℃; for 0.5h;48%
polymer, product derived from polytetrahydrofuran-grafted 5-hydroxypentyl-JandaJel (polytetrahydrofuran wt percent 33.4) with substituted polytetrahydrofuran chain end-OH group on 2-phenylhydrazonopropylcarbonyloxy group

polymer, product derived from polytetrahydrofuran-grafted 5-hydroxypentyl-JandaJel (polytetrahydrofuran wt percent 33.4) with substituted polytetrahydrofuran chain end-OH group on 2-phenylhydrazonopropylcarbonyloxy group

edaravone
89-25-8

edaravone

Conditions
ConditionsYield
With trifluoroacetic acid In acetonitrile at 20℃; for 0.5h;47%
cyclohexanone
108-94-1

cyclohexanone

(Z)-3-(5-Chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-2-cyano-acrylic acid ethyl ester

(Z)-3-(5-Chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-2-cyano-acrylic acid ethyl ester

A

edaravone
89-25-8

edaravone

B

2-Oxo-5,6,7,8-tetrahydro-2H-chromene-3-carbonitrile

2-Oxo-5,6,7,8-tetrahydro-2H-chromene-3-carbonitrile

Conditions
ConditionsYield
With piperidine In ethanol for 8h; Heating;A n/a
B 45%
(Z)-3-(5-Chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-2-cyano-acrylic acid ethyl ester

(Z)-3-(5-Chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-2-cyano-acrylic acid ethyl ester

A

edaravone
89-25-8

edaravone

B

2-Oxo-5,6,7,8-tetrahydro-2H-chromene-3-carbonitrile

2-Oxo-5,6,7,8-tetrahydro-2H-chromene-3-carbonitrile

Conditions
ConditionsYield
With piperidine; cyclohexanone In ethanol for 8h; Heating;A n/a
B 45%
E-1-phenyl-3-methyl-4-<(4-nitrophenyl)methylene>-5-pyrazolone
132603-48-6

E-1-phenyl-3-methyl-4-<(4-nitrophenyl)methylene>-5-pyrazolone

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

A

2-(4-nitrophenyl)benzothiazole
22868-34-4

2-(4-nitrophenyl)benzothiazole

B

edaravone
89-25-8

edaravone

C

4-(4-nitrophenyl)-3-methyl-1-phenylpyrazolo[3,4-b][1,5]benzothiazepine

4-(4-nitrophenyl)-3-methyl-1-phenylpyrazolo[3,4-b][1,5]benzothiazepine

Conditions
ConditionsYield
With acetic acid In ethanol for 3h; Heating;A 15%
B n/a
C 45%
polymer, product derived from polytetrahydrofuran-grafted 5-hydroxypentyl-JandaJel (polytetrahydrofuran wt percent 49.9) with substituted polytetrahydrofuran chain end-OH group on 2-phenylhydrazonopropylcarbonyloxy group

polymer, product derived from polytetrahydrofuran-grafted 5-hydroxypentyl-JandaJel (polytetrahydrofuran wt percent 49.9) with substituted polytetrahydrofuran chain end-OH group on 2-phenylhydrazonopropylcarbonyloxy group

edaravone
89-25-8

edaravone

Conditions
ConditionsYield
With trifluoroacetic acid In acetonitrile at 20℃; for 0.5h;42%
phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

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

ethyl 3-aminobut-2-enoate

edaravone
89-25-8

edaravone

Conditions
ConditionsYield
With potassium acetate In ethanol at 25℃; for 0.75h;40%
phenylhydrazine
100-63-0

phenylhydrazine

resin-OCOCH2COMe

resin-OCOCH2COMe

edaravone
89-25-8

edaravone

Conditions
ConditionsYield
In dichloromethane at 20℃; for 22h;40%
(Z)-3-pyrrolidin-1-yl-but-2-enoic acid ethyl ester
70526-06-6

(Z)-3-pyrrolidin-1-yl-but-2-enoic acid ethyl ester

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

edaravone
89-25-8

edaravone

Conditions
ConditionsYield
With potassium acetate In ethanol at 25℃; for 1.41667h;21%
4-isopropylidene-5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-one
22123-17-7

4-isopropylidene-5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-one

edaravone
89-25-8

edaravone

Conditions
ConditionsYield
With piperidine In benzene for 48h; Product distribution; Ambient temperature;8%
C22H18NO(1+)*I3(1-)
121572-86-9

C22H18NO(1+)*I3(1-)

edaravone
89-25-8

edaravone

6,8-Dimethyl-7-[3-methyl-5-oxo-1-phenyl-1,5-dihydro-pyrazol-(4Z)-ylidene]-2,3-diphenyl-7H-indolizin-1-one
121030-55-5

6,8-Dimethyl-7-[3-methyl-5-oxo-1-phenyl-1,5-dihydro-pyrazol-(4Z)-ylidene]-2,3-diphenyl-7H-indolizin-1-one

Conditions
ConditionsYield
With pyridine for 1h; Ambient temperature;100%
2-(4,6-dimethyl-3-cyano-2-pyridinylthio)benzenediazonium nitrate

2-(4,6-dimethyl-3-cyano-2-pyridinylthio)benzenediazonium nitrate

edaravone
89-25-8

edaravone

4-[(4',6'-dimethyl-3'-cyano-2'-pyridinylthio)-2-phenylhydrazono]-5-methyl-2-phenyl-2,4-dihydropyrazole-3-one

4-[(4',6'-dimethyl-3'-cyano-2'-pyridinylthio)-2-phenylhydrazono]-5-methyl-2-phenyl-2,4-dihydropyrazole-3-one

Conditions
ConditionsYield
Stage #1: 2-(4,6-dimethyl-3-cyano-2-pyridinylthio)benzenediazonium nitrate; 3-methyl-1-phenylpyrazolin-5-(4H)-one for 0.0833333h; grinding;
Stage #2: With trimethylamine at 20℃; under 375.038 Torr; for 12h; Further stages.;
100%
α-bromoacetophenone
70-11-1

α-bromoacetophenone

edaravone
89-25-8

edaravone

(5-methyl-2-phenyl-2H-pyrazol-3-yl) (2-oxo-2-phenylethyl) ether

(5-methyl-2-phenyl-2H-pyrazol-3-yl) (2-oxo-2-phenylethyl) ether

Conditions
ConditionsYield
Stage #1: α-bromoacetophenone; 3-methyl-1-phenylpyrazolin-5-(4H)-one at 20℃; for 1h; ball-milling;
Stage #2: With sodium carbonate Further stages.;
100%
edaravone
89-25-8

edaravone

3-methyl-1-phenyl-1H-pyrazole-5(4H)-thione
22717-42-6

3-methyl-1-phenyl-1H-pyrazole-5(4H)-thione

Conditions
ConditionsYield
With Lawessons reagent In toluene Reflux;100%
With Lawessons reagent In toluene for 2h; Reflux;97%
With Lawessons reagent for 0.0833333h; Irradiation; microwave;70%
With Lawessons reagent In toluene at 110℃; for 2h; Inert atmosphere;
edaravone
89-25-8

edaravone

4-methoxycarbonyl aniline
619-45-4

4-methoxycarbonyl aniline

C18H16N4O3

C18H16N4O3

Conditions
ConditionsYield
Stage #1: 4-methoxycarbonyl aniline With hydrogenchloride; sodium nitrite In water at 0 - 40℃; for 1h;
Stage #2: 3-methyl-1-phenylpyrazolin-5-(4H)-one With sodium hydroxide In water at 2 - 5℃; for 1h;
99.6%
benzoyl chloride
98-88-4

benzoyl chloride

edaravone
89-25-8

edaravone

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

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

Conditions
ConditionsYield
Stage #1: edaravone With potassium hydroxide In water; acetonitrile for 0.5h;
Stage #2: benzoyl chloride In dichloromethane; water; acetonitrile for 0.0833333h;
99%
With triethylamine In chloroform for 1h; Heating;90%
for 0.133333h; microwave irradiation;87%
acetic anhydride
108-24-7

acetic anhydride

edaravone
89-25-8

edaravone

(3-methyl-1-phenyl-1H-pyrazol-5-yl) acetate
138853-66-4

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

Conditions
ConditionsYield
With triethylamine In chloroform for 1h; Heating;99%
at 20℃; for 12h;65%
With 4-ethoxymethylene-2-phenyl-2-oxazolin-5-one at 70 - 80℃;
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

edaravone
89-25-8

edaravone

malononitrile
109-77-3

malononitrile

6-amino-4-(4-chlorophenyl)-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazole
76973-35-8

6-amino-4-(4-chlorophenyl)-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazole

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride In water at 90℃; for 6h;99%
With imidazole spacer and sulfonic acid tagged silica coated magnetite nanoparticle In neat (no solvent) at 20℃; for 0.333333h; Catalytic behavior; Reagent/catalyst; Temperature;98%
With Fe3O4 (at) tris(hydroxymethyl)aminomethane-SO3H nanoparticles In ethanol; water at 100℃; for 0.0833333h;98%
benzaldehyde
100-52-7

benzaldehyde

edaravone
89-25-8

edaravone

malononitrile
109-77-3

malononitrile

6-amino-1,4-dihydro-3-methyl-1,4-diphenylpyrano[2,3-c]pyrazole-5-carbonitrile
53316-57-7

6-amino-1,4-dihydro-3-methyl-1,4-diphenylpyrano[2,3-c]pyrazole-5-carbonitrile

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride In water at 90℃; for 6h;99%
With rac-Pro-OH at 25℃; for 0.0833333h;99%
With trichloroacetic acid at 100℃; for 0.05h; neat (no solvent);98%
benzaldehyde
100-52-7

benzaldehyde

edaravone
89-25-8

edaravone

4,4'-(phenylmethylene)bis(3-methyl-1-phenyl-pyrazol-5-ol)
57303-46-5

4,4'-(phenylmethylene)bis(3-methyl-1-phenyl-pyrazol-5-ol)

Conditions
ConditionsYield
With MCM-41 nanoparticles-supported guanine bonded with zirconium(IV) In ethanol at 80℃; for 0.333333h; Green chemistry; chemoselective reaction;99%
With Mn/lysine(at)CoFe2O4 nanocomposite at 80℃; for 1h;99%
With 3-aminopropylated silica gel In acetonitrile at 20℃; for 0.166667h; tandem Knoevenagel-Michael reaction;98%
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

edaravone
89-25-8

edaravone

malononitrile
109-77-3

malononitrile

6-amino-4-(4-methoxyphenyl)-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
53316-60-2

6-amino-4-(4-methoxyphenyl)-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile

Conditions
ConditionsYield
With rac-Pro-OH at 25℃; for 0.166667h;99%
With sodium fluoride In methanol; water at 25℃; for 0.1h; Sonication;98%
With N-benzyl-N,N,N-triethylammonium chloride In water at 90℃; for 6h;96%
1-(3-methyl-2-butenyl)-pyrrol-2-carbaldehyde
110719-45-4

1-(3-methyl-2-butenyl)-pyrrol-2-carbaldehyde

edaravone
89-25-8

edaravone

2,4-dihydro-5-methyl-4-<1'-(3-methyl-2-butenyl)pyrrol-2-yl>methylene-2-phenyl-3H-pyrazol-3-one
110719-46-5

2,4-dihydro-5-methyl-4-<1'-(3-methyl-2-butenyl)pyrrol-2-yl>methylene-2-phenyl-3H-pyrazol-3-one

Conditions
ConditionsYield
With ethylenediamine diacetic acid In acetonitrile99%
4-nitrobenzenediazonium chloride
100-05-0

4-nitrobenzenediazonium chloride

edaravone
89-25-8

edaravone

5-methyl-4-(2-(4-nitrophenyl)hydrazono)-2-phenyl-2,4-dihydro-3H-pyrazol-3one

5-methyl-4-(2-(4-nitrophenyl)hydrazono)-2-phenyl-2,4-dihydro-3H-pyrazol-3one

Conditions
ConditionsYield
With trimethylamine at 20℃; under 375.038 Torr; for 12h;99%
4-methoxy-benzenediazonium; nitrate

4-methoxy-benzenediazonium; nitrate

edaravone
89-25-8

edaravone

4-(4-methoxyphenylhydrazono)-3-methyl-1-phenyl-4,5-dihydropyrazole-5-one

4-(4-methoxyphenylhydrazono)-3-methyl-1-phenyl-4,5-dihydropyrazole-5-one

Conditions
ConditionsYield
With trimethylamine at 20℃; under 375.038 Torr; for 12h;99%
4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

edaravone
89-25-8

edaravone

3-methyl-1-phenyl-1H-pyrazol-5-yl 4-methylbenzoate

3-methyl-1-phenyl-1H-pyrazol-5-yl 4-methylbenzoate

Conditions
ConditionsYield
Stage #1: edaravone With potassium hydroxide In water; acetonitrile for 0.5h;
Stage #2: 4-methyl-benzoyl chloride In dichloromethane; water; acetonitrile for 0.0833333h;
99%
for 0.133333h; microwave irradiation;37%
4-chloro-benzoyl chloride
122-01-0

4-chloro-benzoyl chloride

edaravone
89-25-8

edaravone

(3-methyl-1-phenyl-1H-pyrazol-5-yl) 4-chlorobenzoate

(3-methyl-1-phenyl-1H-pyrazol-5-yl) 4-chlorobenzoate

Conditions
ConditionsYield
With triethylamine In chloroform for 1h; Heating;99%
for 0.133333h; microwave irradiation;81%
With 1,1-dichloroethane; triethylamine at 50 - 60℃;
4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

edaravone
89-25-8

edaravone

malononitrile
109-77-3

malononitrile

3-methyl-6-amino-5-cyano-4-(4-methylphenyl)-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazole
53316-59-9

3-methyl-6-amino-5-cyano-4-(4-methylphenyl)-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazole

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride In water at 90℃; for 6h;99%
With imidazole spacer and sulfonic acid tagged silica coated magnetite nanoparticle In neat (no solvent) at 20℃; for 0.75h;94%
With [amberlite IRA900OH]-supported L-prolinate In ethanol for 0.3h; Catalytic behavior; Reflux;94%
2,4-dichlorobenzaldeyhde
874-42-0

2,4-dichlorobenzaldeyhde

edaravone
89-25-8

edaravone

malononitrile
109-77-3

malononitrile

6-amino-4-(2, 4-dichlorophenyl)-3-methyl-1-phenyl-1,4-dihydropyrano[2, 3-c]pyrazole-5-carbonitrile

6-amino-4-(2, 4-dichlorophenyl)-3-methyl-1-phenyl-1,4-dihydropyrano[2, 3-c]pyrazole-5-carbonitrile

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride In water at 90℃; for 6h;99%
With imidazole spacer and sulfonic acid tagged silica coated magnetite nanoparticle In neat (no solvent) at 20℃; for 0.25h;97%
With triethylammonium acetate at 20℃; for 0.5h;96%
pyridoxal hydrochloride
65-22-5

pyridoxal hydrochloride

edaravone
89-25-8

edaravone

1-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-6-methyl-1,3-dihydro-furo[3,4-c]pyridin-7-ol
854010-13-2

1-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-6-methyl-1,3-dihydro-furo[3,4-c]pyridin-7-ol

Conditions
ConditionsYield
With sodium carbonate In water at 10 - 20℃; pH=2.04; Reagent/catalyst; pH-value;99%
With sodium hydroxide In water at 20℃; for 0.5h;6.8%
With sodium hydroxide In water at 20 - 30℃; for 2h; pH=6.3 - 12.1; Time;
4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

edaravone
89-25-8

edaravone

4,4′-[(4-flurophenyl)methylene]-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)

4,4′-[(4-flurophenyl)methylene]-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)

Conditions
ConditionsYield
In ethanol at 78℃; for 0.0833333h; Green chemistry;99%
With 2-carbamoylhydrazine-1-sulfonic acid In neat (no solvent) at 60℃; for 0.416667h; Reagent/catalyst; Green chemistry;97%
With phosphomolybdic acid In ethanol at 20℃; for 4h;94%
N,N-phenylbistrifluoromethane-sulfonimide
37595-74-7

N,N-phenylbistrifluoromethane-sulfonimide

edaravone
89-25-8

edaravone

trifluoromethanesulfonic acid 5-methyl-2-phenyl-2H-pyrazol-3-yl ester
276249-49-1

trifluoromethanesulfonic acid 5-methyl-2-phenyl-2H-pyrazol-3-yl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 35℃; for 3h;99%
(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

edaravone
89-25-8

edaravone

(R)-5-methyl-4-(2-nitro-1-phenylethyl)-2-phenyl-2H-pyrazol-3-ol
1440200-00-9

(R)-5-methyl-4-(2-nitro-1-phenylethyl)-2-phenyl-2H-pyrazol-3-ol

Conditions
ConditionsYield
With quinine In chloroform at 20℃; for 4h; Solvent; Temperature; Reagent/catalyst; Michael Addition; enantioselective reaction;99%
With C33H30F6N4O3 In dichloromethane at 20℃; for 24h; Michael Addition; Inert atmosphere; enantioselective reaction;96%
With C31H39N3O9S; benzoic acid In toluene at 20℃; Inert atmosphere;95%
With C29H32N4O2S In chloroform at -30℃; for 12h; Michael Addition; enantioselective reaction;95.3%
With C40H31F6N3O2 In 1,2-dichloro-ethane at 20℃; for 24h; Catalytic behavior; Reagent/catalyst; Solvent; Michael Addition; enantioselective reaction;93%
1-chloro-4-(2-nitrovinyl)benzene
706-07-0

1-chloro-4-(2-nitrovinyl)benzene

edaravone
89-25-8

edaravone

(R)-4-(1-(4-chlorophenyl)-2-nitroethyl)-3-methyl-1-phenyl-1H-pyrazol-5-ol
1451195-14-4

(R)-4-(1-(4-chlorophenyl)-2-nitroethyl)-3-methyl-1-phenyl-1H-pyrazol-5-ol

Conditions
ConditionsYield
With quinine In chloroform at 20℃; for 4h; Michael Addition; enantioselective reaction;99%
With C31H39N3O9S; benzoic acid In toluene at 20℃; for 12h; Schlenk technique; Inert atmosphere; enantioselective reaction;99%
With C40H31F6N3O2 In 1,2-dichloro-ethane at 20℃; for 18h; Michael Addition; enantioselective reaction;95%
With C29H32N4O2S In chloroform at -30℃; for 12h; Michael Addition; enantioselective reaction;93.7%
With C31H39N3O9S; benzoic acid In toluene at 20℃; Inert atmosphere;
terephthalaldehyde,
623-27-8

terephthalaldehyde,

edaravone
89-25-8

edaravone

4,4'-(1,4-phenylenebis(methanylylidene))bis(3-methyl-1-phenyl-1H-pyrazol)-5(4H)-one
306765-12-8

4,4'-(1,4-phenylenebis(methanylylidene))bis(3-methyl-1-phenyl-1H-pyrazol)-5(4H)-one

Conditions
ConditionsYield
With sulfuric acid-modified polyethyleneglycol-6000 In neat (no solvent) at 70℃; for 0.05h; Knoevenagel Condensation; Green chemistry;99%
3-nitro-β-nitrostyrene
882-26-8

3-nitro-β-nitrostyrene

edaravone
89-25-8

edaravone

(R)-3-methyl-4-(2-nitro-1-(3-nitrophenyl)ethyl)-1-phenyl-1H-pyrazol-5-ol
1451195-21-3

(R)-3-methyl-4-(2-nitro-1-(3-nitrophenyl)ethyl)-1-phenyl-1H-pyrazol-5-ol

Conditions
ConditionsYield
With quinine In chloroform at 20℃; for 6h; Michael Addition; enantioselective reaction;99%
With C29H32N4O2S In chloroform at -30℃; for 18h; Michael Addition; enantioselective reaction;93.2%
With C40H31F6N3O2 In 1,2-dichloro-ethane at 20℃; for 24h; Michael Addition; enantioselective reaction;92%
2-cyclohexyl-1-nitroethene
50598-92-0

2-cyclohexyl-1-nitroethene

edaravone
89-25-8

edaravone

(R)-4-(1-cyclohexyl-2-nitro-ethyl)-5-methyl-2-phenyl-2H-pyrazol-3-ol
1451195-27-9

(R)-4-(1-cyclohexyl-2-nitro-ethyl)-5-methyl-2-phenyl-2H-pyrazol-3-ol

Conditions
ConditionsYield
With quinine In chloroform at 20℃; for 12h; Michael Addition; enantioselective reaction;99%
nitrostyrene
5153-67-3

nitrostyrene

edaravone
89-25-8

edaravone

(R)-5-methyl-4-(2-nitro-1-phenylethyl)-2-phenyl-2H-pyrazol-3-ol
1440200-00-9

(R)-5-methyl-4-(2-nitro-1-phenylethyl)-2-phenyl-2H-pyrazol-3-ol

Conditions
ConditionsYield
With C31H39N3O9S; benzoic acid In toluene at 20℃; for 12h; Reagent/catalyst; Solvent; Time; Schlenk technique; Inert atmosphere; enantioselective reaction;99%
Stage #1: nitrostyrene With (S)-3-(3,5-bis(trifluoromethyl)phenylamino)-4-(1-phenyl-2-(piperidin-1-yl)ethylamino)cyclobut-3-ene-1,2-dione In 1,2-dichloro-ethane for 0.166667h; Michael Addition; Inert atmosphere;
Stage #2: edaravone In 1,2-dichloro-ethane at 20℃; for 24h; Michael Addition; Inert atmosphere; enantioselective reaction;
n/a
1-naphthaldehyde
66-77-3

1-naphthaldehyde

edaravone
89-25-8

edaravone

4,4'-(naphthalen-1-ylmethanediyl)bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)
1433750-55-0

4,4'-(naphthalen-1-ylmethanediyl)bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)

Conditions
ConditionsYield
With 2-carbamoylhydrazine-1-sulfonic acid In neat (no solvent) at 60℃; for 0.75h; Reagent/catalyst; Green chemistry;99%
With zinc(II) oxide In ethanol; water for 0.5h; Catalytic behavior; Reflux;93%
Stage #1: 1-naphthaldehyde; 3-methyl-1-phenylpyrazolin-5-(4H)-one With zinc(II) oxide In ethanol; water Knoevenagel Condensation; Reflux; Green chemistry;
Stage #2: With zinc(II) oxide In ethanol; water Michael Addition; Reflux; Green chemistry;
90%
3-nitro-2H-1-benzopyran
92210-53-2

3-nitro-2H-1-benzopyran

edaravone
89-25-8

edaravone

C19H17N3O4

C19H17N3O4

Conditions
ConditionsYield
With quinine In dichloromethane at -15℃; for 96h; Catalytic behavior; Solvent; Temperature; Reagent/catalyst; Michael Addition; enantioselective reaction;99%

89-25-8Relevant articles and documents

Structure and extractive ability of 1-alkyl- and 3-methyl-1-phenyl-2- pyrazolin-5-ones

Lesnov,Sazonova,Pavlov

, p. 298 - 302 (2005)

Extractive ability of 1-substituted 3-methylpyrazol-5-ones (LH) is studied. From acidic chloride complexes, ionic thallium(III) associates (LH 2)[TlCl4] are extracted; from trichloroacetate, coordination scandium complexes Sc(LH)4(CCl3COO) 3; and from ammine, copper(II) complexes CuL2. The extractive ability decreases in the order R = C7H15 > C6H13 > C5H11 > C 6H5 > C4H9. 2005 Pleiades Publishing, Inc.

Synthesis and Herbicidal Activity of 5-Heterocycloxy-3-methyl-1-substituted-1H-pyrazoles

Kang, Jing,Yue, Xia Li,Chen, Chang Shui,Li, Jian Hong,Ma, Hong Ju

, (2016)

With the objective of finding valuable herbicidal candidates, a series of new 5-heterocycloxy- 3-methyl-1-substituted-1H-pyrazoles were synthesized and their herbicidal activities were evaluated. The bioassay results showed that some compounds exhibited e

Catalytic Asymmetric Addition of Diorganozinc Reagents to Pyrazole-4,5-Diones and Indoline-2,3-Diones

Wang, Rong-Hui,Li, Ya-Ling,He, Hong-Jiao,Xiao, You-Cai,Chen, Fen-Er

supporting information, p. 4302 - 4306 (2021/02/16)

The catalytic enantioselective diorganozinc additions to cyclic diketones including pyrazolin-4,5-diones and isatins have been developed. In the presence of morpholine-containing chiral amino alcohol ligand, the corresponding chiral cyclic tertiary alcohols were produced in good to excellent yields (up to 97 %) and enantioselectivities (up to 95 % ee). The notable feature of this protocol includes its mild reaction conditions, Lewis acid additives free and broad functional group tolerance.

Scale-Up of a Continuous Manufacturing Process of Edaravone

He, Yan,Hong, Qingxia,Mei, Wenliu,Sun, Tiemin,Wu, Chengjun,Zhou, Shuhao

, p. 2146 - 2153 (2021/09/13)

Edaravone belongs to a class of brain-protective agents, which can scavenge free radicals. To reduce impurities and improve the yield, a continuous flow production process of edaravone was developed. The synthesis is continuously carried out in two steps. The throughput can reach 11.328 kg/day and the purity of the final product is 99.95%, which are in accordance with the needs of production. This is an efficient and quick production process suitable for industrial production.

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