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Chemical Structure| 89-25-8 Chemical Structure| 89-25-8
Chemical Structure| 89-25-8

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Edaravone is a novel, potent free radical scavenger that inhibits MMP-9-related brain hemorrhage in rats treated with tissue plasminogen activator.

Synonyms: MCI-186; NSC 2629; Arone

4.5 *For Research Use Only !

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Product Details of Edaravone

CAS No. :89-25-8
Formula : C10H10N2O
M.W : 174.20
SMILES Code : O=C1CC(C)=NN1C2=CC=CC=C2
Synonyms :
MCI-186; NSC 2629; Arone
MDL No. :MFCD00003138
InChI Key :QELUYTUMUWHWMC-UHFFFAOYSA-N
Pubchem ID :4021

Safety of Edaravone

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Edaravone

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 89-25-8 ]

[ 89-25-8 ] Synthesis Path-Downstream   1~22

  • 3
  • [ 92-55-7 ]
  • [ 89-25-8 ]
  • 5-Methyl-4-[1-(5-nitro-furan-2-yl)-meth-(E)-ylidene]-2-phenyl-2,4-dihydro-pyrazol-3-one [ No CAS ]
  • 4
  • [ 71-33-0 ]
  • [ 89-25-8 ]
  • [ 108-19-0 ]
  • [ 61466-03-3 ]
  • 5
  • [ 71-33-0 ]
  • [ 89-25-8 ]
  • [ 61466-03-3 ]
  • 6
  • [ 122-51-0 ]
  • [ 89-25-8 ]
  • [ 13214-64-7 ]
  • 4-methoxy-<i>N</i>-(3-methyl-6-oxo-1-phenyl-1,6-dihydro-pyrano[2,3-<i>c</i>]pyrazol-5-yl)-benzamide [ No CAS ]
  • 7
  • [ 89-25-8 ]
  • [ 4494-26-2 ]
  • 1-(2-deoxypentafuranosyl)-5-(3-methyl-5-oxo-1-phenyl-4,5-dihydro-pyrazol-4-ylidene)pyrimidine-2,4(1H,3H)-dione [ No CAS ]
  • 8
  • [ 89-25-8 ]
  • [ 4494-26-2 ]
  • [ 898225-09-7 ]
  • 9
  • [ 34595-26-1 ]
  • [ 89-25-8 ]
  • C22H23N3O [ No CAS ]
  • 10
  • [ 463-49-0 ]
  • [ 156150-67-3 ]
  • [ 89-25-8 ]
  • 4,4-bis[(3-chloro-4-fluorophenyl)prop-2-en-1-yl]-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one [ No CAS ]
  • 11
  • [ 34595-26-1 ]
  • [ 89-25-8 ]
  • 3'-methyl-1',3-diphenyl-2,3,4,4a,5,6-hexahydro-1H-spiro-[benzo[c]quinolizine-5,4'-pyrazol]-5'-one [ No CAS ]
  • 12
  • [ 42059-80-3 ]
  • [ 89-25-8 ]
  • [ 1379795-54-6 ]
  • 14
  • [ 399-25-7 ]
  • [ 89-25-8 ]
  • (R)-4-[1-(2-fluorophenyl)-2-nitroethyl]-5-methyl-2-phenyl-2H-pyrazol-3-ol [ No CAS ]
  • 15
  • [ 68-12-2 ]
  • [ 89-25-8 ]
  • [ 186130-62-1 ]
  • 16
  • [ 10102-94-0 ]
  • [ 89-25-8 ]
  • C20H16BrN3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water; at 100℃; for 0.5h;Green chemistry; General procedure: A mixture of 5 (2.0 mmol) which were prepared by literature method,28 pyrazolone 2 (0.35 g, 2.0 mmol),30 mL of distilled water refluxed at 100 C for about 30 min. At the end of this period, the product was separated as an orange colour solid. The reaction mass was, filtered, washed with 10 mL of ethanol and dried to obtain crude 4, which on recrystallization from suitable solvent to gave pure 4.
  • 17
  • [ 34595-26-1 ]
  • [ 89-25-8 ]
  • C22H23N3O [ No CAS ]
  • C22H23N3O [ No CAS ]
  • 18
  • [ 3621-82-7 ]
  • [ 89-25-8 ]
  • 6-chloro-2-((3-methyl-1-phenyl-1H-pyrazol-5-yl)oxy)-1,3-benzoxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
64.5% With potassium carbonate; In dimethyl sulfoxide; at 20℃; for 3h; General procedure: Compound 5a (1.5 mmol) and powdered potassium carbonate (2.25 mmol) were added into dimethylsulfoxide (20 mL). 2, 6-Dichlorobenzoxazole (1.5 mmol) was added to the solution and the mixture was stirred at room temperature for 3 h. The mixture was diluted with water (20 mL) and extracted with diethyl ether (30 mL 2). The extract was washed with water and saturated brine, dried over anhydrous sodium sulfate, the filtrate was concentrated in vacuo. The residue was further purified by silica gel column chromatography (ethyl acetate/petroleum ether: 1/10 as the eluent) to give compound 6a as a white solid. Compounds 6b?i were synthesized using the same procedures.
64.5% With potassium carbonate; In dimethyl sulfoxide; at 20℃; for 4h; In a 50mL single-mouth bottle,Add 1.74 g (10 mmol) of 3-methyl-1-phenyl-5-pyrazolone,Dimethyl sulfoxide (30 mL) as a solvent,Then add 1.8g (10mmol, 99percent) of <strong>[3621-82-7]2,6-dichlorobenzoxazole</strong>.Potassium carbonate (15mmol, 2.07g) is used as an acid binding agent.Stir at room temperature for 4 h,When TLC monitoring no longer has raw material points,Stop the reaction,Pour into the water,The solid is precipitated and separated and purified by a silica gel column.The volume ratio of the eluent petroleum ether to ethyl acetate is 20:1.Concentrated and concentrated under reduced pressure to give a white solid3-methyl-1-phenyl-5-(2-(6-chlorobenzoxazolyl)oxy)-1H-pyrazole 2.1 g,The yield was 64.5percent.
  • 19
  • [ 399-25-7 ]
  • [ 89-25-8 ]
  • (S)-4-(1-(2-fluorophenyl)-2-nitroethyl)-3-methyl-1-phenyl-1H-pyrazol-5-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With C40H31F6N3O2; In 1,2-dichloro-ethane; at 20℃; for 18h; General procedure: To a stirred solution of 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one (1a, 52.2 mg, 0.3 mmol) and catalyst III (2.1 mg, 3 μmol) in DCE (3.0 mL) was added β-nitrostyrene (2a, 44.7 mg, 0.3 mmol) at room temperature.The reaction mixture was stirred for 24 h at room temperature. After completion of the reaction, the resulting solution was concentrated in vacuo and the obtained residue was purified by flash column chromatography (EtOAc:Hex, 1:2) to afford (R)-3-methyl-4-(2-nitro-1-phenylethyl)-1-phenyl-1H-pyrazol-5-ol (3a, 93 yield, 90 mg).
  • 20
  • [ 98-32-8 ]
  • [ 89-25-8 ]
  • 4-Hydroxy-3-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-ylazo)-benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
(Step 1). After adding 50 parts of <strong>[98-32-8]3-amino-4-hydroxyphenylsulfonamide</strong> to 400 parts of water, a 25percent sodium hydroxide aqueous solution was added to obtain an aqueous solution having a pH of 7.5 to 8.0. After adding 31 parts of 35percent hydrochloric acid to this aqueous solution, the temperature was adjusted to 5 to 10 ° C. in an ice bath, 49.6 parts of 40percent aqueous solution of sodium nitrite was added, after reacting at the same temperature for about 30 minutes, 2.1 parts of acid was added and stirred for 5 minutes to obtain a diazo reaction solution.On the other hand, 44.2 parts of 3-methyl-1-phenylpyrazolone was added to 400 parts of water, and then a 25percent sodium hydroxide aqueous solution was added to obtain an aqueous solution having a pH of 8.5 to 9.0. The temperature was further raised to 5 to 10 ° C. in an ice bath. The diazo reaction solution obtained above was added dropwise to this aqueous solution over a period of 15 minutes while maintaining the pH at 8.5 to 9.0 and the temperature at 5 to 10 ° C. by adding a 25percent sodium hydroxide aqueous solution as needed The reaction was further continued for 3 hours while maintaining the pH at 8.5 to 9.0 and the temperature at 5 to 10 ° C. The precipitated solid was collected by filtration to obtain 295 parts of the compound represented by the following formula (6) It was obtained as a wet cake.
  • 21
  • [ 25365-71-3 ]
  • [ 89-25-8 ]
  • 3‐methyl‐1‐phenyl‐4‐((2‐phenyl‐1H‐indol‐3‐yl)methylene)‐1H‐pyrazol‐5(4H)‐one [ No CAS ]
  • 22
  • [ 2737-22-6 ]
  • [ 89-25-8 ]
  • 5-methyl-2-phenyl-4-(2,4,6-tribromo-3-hydroxybenzylidene)-2,4-dihydro-3H-pyrazol-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With acetic acid; In ethanol; at 55℃; General procedure: Building blocks for moieties I (1.0 equiv), II (1.2 equiv), and acetic acid (2.0 equiv) in ethanol were stirred at 55 C for 3-5 h. After coolingto room temperature, the products were precipitated, filtered, andcollected, then purified by column chromatography using PE-EA orMeOH-DCM as an eluent.
 

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