ChemicalBook > CAS DataBase List > 5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one

5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one

Product Name:
5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one
CAS No.
89-25-8
Chemical Name:
5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one
CBNumber:
CB1287462
Molecular Formula:
C10H10N2O
Formula Weight:
174.2
MOL File:
89-25-8.mol
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5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one Property

Melting point:
126-128 °C(lit.)
Boiling point:
287 °C265 mm Hg(lit.)
Density 
1,12 g/cm3
refractive index 
1.6300 (estimate)
Flash point:
191°C/17mm
storage temp. 
Store at RT
solubility 
3.30g/l
pka
2.73±0.50(Predicted)
form 
Crystalline Powder
color 
Yellow to beige
PH
4.0-4.4 (H2O, 20℃)(saturated aqueous solution)
Water Solubility 
3 g/L (20 ºC)
Merck 
14,6713
BRN 
609575
InChIKey
QELUYTUMUWHWMC-UHFFFAOYSA-N
CAS DataBase Reference
89-25-8(CAS DataBase Reference)
NIST Chemistry Reference
3H-Pyrazol-3-one, 2,4-dihydro-5-methyl-2-phenyl-(89-25-8)
EPA Substance Registry System
1-Phenyl-3-methyl-5-pyrazolone (89-25-8)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
1
RTECS 
UQ9625000
TSCA 
Yes
HS Code 
29331990
Hazardous Substances Data
89-25-8(Hazardous Substances Data)
Toxicity
LD50 orl-rat: 3500 mg/kg LONZA# 08FEB79
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N-Bromosuccinimide Price More Price(16)

Sigma-Aldrich Gold
Product number:
443300
Product name :
MCI-186
Packaging:
500mg
Price:
$75.2
Updated:
2019/12/02
Buy:
Buy
Sigma-Aldrich Gold
Product number:
1040016
Product name :
Antipyrine Related Compound A
Purity:
United States Pharmacopeia (USP) Reference Standard
Packaging:
25mg
Price:
$1212.75
Updated:
2019/12/02
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Buy
TCI Chemical Gold
Product number:
M0687
Product name :
3-Methyl-1-phenyl-5-pyrazolone
Purity:
>98.0%(HPLC)(T)
Packaging:
25g
Price:
$17
Updated:
2019/12/02
Buy:
Buy
TCI Chemical Gold
Product number:
M0687
Product name :
3-Methyl-1-phenyl-5-pyrazolone
Purity:
>98.0%(HPLC)(T)
Packaging:
500g
Price:
$36
Updated:
2019/12/02
Buy:
Buy
Alfa Aesar Gold
Product number:
A11161
Product name :
3-Methyl-1-phenyl-2-pyrazolin-5-one, 98+%
Packaging:
500g
Price:
$37.4
Updated:
2019/12/02
Buy:
Buy
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5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one Chemical Properties,Usage,Production

Description

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.

Chemical Properties

Off white to light yellow powder

Originator

Mitsubishi Pharma (Japan)

Uses

antioxidant, lipoxygenase inhibitor

Uses

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

Hazard

Toxic by ingestion.

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.

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.]

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89-25-8, 5-Methyl-2-phenyl-1,2-dihydropyrazol-3-oneRelated Search:

1-PHENYLPYRAZOLE Oxazoline 3-Methyl-2-pyrazolin-5-one Pyrazole Paraquat dichloride Methylparaben 2,6-Dimethyl-7-octen-2-ol Methyl 5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one PHENYL VALERATE Kresoxim-methyl Methanol Methyl acrylate Basic Violet 1 Cefazolin sodium salt Methyl acetate Acetonitrile Cefazolin
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